From e97f7369339b215fda7d0169b567a211db6c5c38 Mon Sep 17 00:00:00 2001 From: Christoph Helma Date: Sun, 7 Oct 2018 19:39:34 +0200 Subject: Rakefile instead of Makefile and scripts --- Dockerfile | 6 +- Makefile | 68 ++-- Rakefile | 165 ++++++++++ data/PA_complete_SMILES.csv | 676 -------------------------------------- data/PA_complete_SMILES_fixed.csv | 602 --------------------------------- data/efsa.csv | 1 + data/hansen.csv | 1 + data/mutagenicity-merged.id | 2 +- scripts/carcinogenicity2csv.rb | 25 -- scripts/convert_pa.rb | 12 - scripts/efsa2csv.rb | 28 -- scripts/import-csv.rb | 8 - 12 files changed, 213 insertions(+), 1381 deletions(-) create mode 100644 Rakefile delete mode 100644 data/PA_complete_SMILES.csv delete mode 100644 data/PA_complete_SMILES_fixed.csv delete mode 100755 scripts/carcinogenicity2csv.rb delete mode 100755 scripts/convert_pa.rb delete mode 100755 scripts/efsa2csv.rb delete mode 100755 scripts/import-csv.rb diff --git a/Dockerfile b/Dockerfile index 2222d87..3932e6f 100644 --- a/Dockerfile +++ b/Dockerfile @@ -42,11 +42,11 @@ RUN git clone https://github.com/opentox/lazar.git WORKDIR lazar RUN git checkout "development" RUN ruby ext/lazar/extconf.rb -RUN gem install bundler +RUN gem install bundler rake RUN bundle install RUN git checkout -b "mutanew" -USER root -RUN pacman -S catdoc +#USER root +#RUN pacman -S catdoc # set environment vars # start mongo and R USER ist diff --git a/Makefile b/Makefile index 6ce86d3..015f075 100644 --- a/Makefile +++ b/Makefile @@ -4,6 +4,17 @@ summaries = summaries/weighted_majority_merged_sim0.1.json summaries/weighted_ma all: $(summaries) +# exports + +export/mutagenicity-merged.sdf: data/mutagenicity-merged.id + scripts/export.rb $< sdf > $@ + +export/mutagenicity-merged.csv: data/mutagenicity-merged.id + scripts/export.rb $< > $@ + +export/carcinogenicity.csv: data/carcinogenicity.id + scripts/export.rb $< > $@ + summaries/pa_carcinogenicity_neighbor_sets.json: experiments/pa_carcinogenicity_prediction.json scripts/pa_neighbor_sets.rb $< > $@ @@ -34,43 +45,37 @@ summaries/weighted_majority_merged_sim0.1.json: experiments/weighted_majority_me experiments/weighted_majority_merged_sim0.1.id: data/mutagenicity-merged.csv scripts/repeated_crossvalidation.rb $< > $@ -experiments/pa_carcinogenicity_prediction.json: data/carcinogenicity.csv data/PA_complete_SMILES_fixed.csv +experiments/pa_carcinogenicity.id: data/carcinogenicity.id data/PA.id scripts/predict.rb $^ > $@ -experiments/pa_mutagenicity_prediction.json: data/mutagenicity-merged.csv data/PA_complete_SMILES_fixed.csv +experiments/pa_mutagenicity.id: data/mutagenicity-merged.id data/PA.id scripts/predict.rb $^ > $@ -# test data - -data/PA_complete_SMILES_fixed.csv: data/PA.sdf - cat $< | scripts/convert_pa.rb > $@ - -data/PA_complete_SMILES_fixed.csv: data/PA_complete_SMILES.csv - cat $< | scripts/convert_pa.rb > $@ - -# training data +# models -export/mutagenicity-merged.sdf: data/mutagenicity-merged.id - scripts/export-sdf.rb $< > $@ +models/mutagenicity-merged.id: data/mutagenicity-merged.id + scripts/merge.rb $^ > $@ -data/mutagenicity-merged.id: data/mutagenicity-merged.csv - scripts/import-csv.rb $< > $@ +models/carcinogenicity.id: data/carcinogenicity.id + scripts/import-pubchem.rb 1205 -data/mutagenicity-merged.csv: $(data) - scripts/merge-mutagenicity.rb $(data) > $@ +# test data -data/carcinogenicity.csv: data/aid1205.csv - scripts/carcinogenicity2csv.rb $< > $@ +data/PA.id: data/PA.sdf + scripts/import.rb $< sdf > $@ + +# training data -# carcinogenicity +data/mutagenicity-merged.id: data/hansen.id data/kazius.id data/efsa.id + scripts/merge.rb $^ > $@ -data/aid1205.csv: - cd data && curl https://pubchem.ncbi.nlm.nih.gov/rest/pug/assay/aid/1205/CSV -o $@ +data/carcinogenicity.id: + scripts/import-pubchem.rb 1205 # kazius -data/kazius.csv: data/cas_4337.sdf - scripts/kazius2csv.rb $< > $@ +data/kazius.id: data/cas_4337.sdf + scripts/import.rb $< sdf > $@ data/cas_4337.sdf: data/cas_4337.zip cd data && unzip cas_4337.zip @@ -80,8 +85,11 @@ data/cas_4337.zip: # efsa +data/efsa.id: data/efsa.csv + scripts/import.rb $< > $@ + data/efsa.csv: data/GENOTOX_data_and_dictionary.tsv - scripts/efsa2csv.rb $< > $@ + scripts/efsa2csv.rb $< > $@ data/GENOTOX_data_and_dictionary.tsv: data/GENOTOX_data_and_dictionary.xls xls2csv -s cp1252 -d utf-8 -x -c " " $< > $@ @@ -91,11 +99,19 @@ data/GENOTOX_data_and_dictionary.xls: # hansen +data/hansen.id: data/hansen.csv + scripts/import.rb $< > $@ + data/hansen.csv: data/Mutagenicity_N6512.csv scripts/hansen2csv.rb $< > $@ data/Mutagenicity_N6512.csv: cd data && wget "http://doc.ml.tu-berlin.de/toxbenchmark/Mutagenicity_N6512.csv" +# cleanup + clean: - rm data/hansen.csv + rm data/*.id + +cleanall: + rm data/* diff --git a/Rakefile b/Rakefile new file mode 100644 index 0000000..5d63b4f --- /dev/null +++ b/Rakefile @@ -0,0 +1,165 @@ +#!/usr/bin/env ruby +require_relative '../lazar/lib/lazar.rb' +include OpenTox + +#task :default => ["predictions/PA_mutagenicity.id","validations/mutagenicity-merged.id"] +task :default => ["predictions/PA_mutagenicity.id"] + +# summaries +# predictions + +file "predictions/PA_mutagenicity.id" => ["models/mutagenicity-merged.id", "data/PA.id"] do |t| predict t end +file "predictions/PA_carcinogenicity.id" => ["models/carcinogenicity.id", "data/PA.id"] do |t| predict t end + +# validations + +file "validations/mutagenicity-merged.id" => "models/mutagenicity-merged.id" do |t| validate_model t end +file "validations/carcinogenicity.id" => "models/carcinogenicity.id" do |t| validate_model t end + +# models + +file "models/mutagenicity-merged.id" => "data/mutagenicity-merged.id" do |t| create_model t end +file "models/carcinogenicity.id" => "data/carcinogenicity.id" do |t| create_model t end + +# test data + +file "data/PA.id" => "data/PA.sdf" do |t| import_sdf t end + +# training data + +file "data/mutagenicity-merged.id" => ["data/hansen.id", "data/kazius.id", "data/efsa.id"] do |t| + input = t.prerequisites.collect{|id| Dataset.find(File.read(id).chomp)} + source_feature = Feature.where(:name => "Ames test categorisation").first # Kazius + target_feature = Feature.where(:name => "Mutagenicity").first + merged = Dataset.merge input, {source_feature => target_feature}, {1 => "mutagen", 0 => "nonmutagen"} + File.open(t.name,"w+") { |f| f.puts merged.id } +end + +file "data/carcinogenicity.id" do |t| + File.open(t.name,"w+") do |f| + d = Dataset.from_pubchem 1205 + f.puts d.id + end +end + +# kazius + +file "data/kazius.id" => "data/cas_4337.sdf" do |t| import_sdf t end + +file "data/cas_4337.sdf" => "data/cas_4337.zip" do |t| + `cd data && unzip cas_4337.zip` +end + +file "data/cas_4337.zip" do + `cd data && wget "http://cheminformatics.org/datasets/bursi/cas_4337.zip"` +end + +# efsa + +file "data/efsa.id" => "data/efsa.csv" do |t| import_csv t end + +file "data/efsa.csv" => "data/GENOTOX_data_and_dictionary.tsv" do |t| efsa2csv t end + +file "data/GENOTOX_data_and_dictionary.tsv" => "data/GENOTOX_data_and_dictionary.xls" do |t| + `xls2csv -s cp1252 -d utf-8 -x -c " " #{t.name} > #{t.prerequisites[0]}` +end + +file "data/GENOTOX_data_and_dictionary.xls" do |t| + `cd data && wget "https://data.europa.eu/euodp/data/storage/f/2017-07-19T142131/GENOTOX%20data%20and%20dictionary.xls" -o #{t.name}` +end + +# hansen + +file "data/hansen.id" => "data/hansen.csv" do |t| import_csv t end + +file "data/hansen.csv" => "data/Mutagenicity_N6512.csv" do |t| + File.open(t.name,"w+") do |f| + i = 0 + CSV.foreach(t.prerequisites[0]) do |row| + if i == 0 + f.puts "ID,SMILES,Mutagenicity" + else + c = OpenTox::Compound.from_smiles(row[5]).smiles + f.puts ["hansen_#{row[0]}",c, row[2]].join "," + end + i += 1 + end + end +end + +file "data/Mutagenicity_N6512.csv" do + `cd data && wget "http://doc.ml.tu-berlin.de/toxbenchmark/Mutagenicity_N6512.csv"` +end + +# cleanup + +task :clean do `rm data/*id` end +task :cleanall do `rm data/*` end + +# functions + +def import_csv t + File.open(t.name,"w+") do |f| + d = Dataset.from_csv_file t.prerequisites[0] + f.puts d.id + end +end + +def import_sdf t + File.open(t.name,"w+") do |f| + d = Dataset.from_sdf_file t.prerequisites[0] + f.puts d.id + end +end + +def efsa2csv t + File.open(t.name,"w+") do |f| + i = 0 + db = {} + CSV.foreach(t.prerequisites[0], :encoding => "UTF-8", :col_sep => "\t", :liberal_parsing => true) do |row| + if i > 0 and row[11] and !row[11].empty? and row[24].match(/Salmonella/i) and ( row[25].match("TA 98") or row[25].match("TA 100") ) and row[33] + begin + c = OpenTox::Compound.from_smiles(row[11].gsub('"','')).smiles + rescue + c = OpenTox::Compound.from_inchi(row[12]).smiles # some smiles (row[11]) contain non-parseable characters + end + db[c] ||= {} + db[c][:id] ||= "efsa_#{row[2]}" + if row[33].match(/Positiv/i) + db[c][:value] = 1 # at least one positive result in TA 98 or TA 100 + elsif row[33].match(/Negativ/i) + db[c][:value] ||= 0 + end + end + i += 1 + end + + f.puts "ID,SMILES,Mutagenicity" + db.each do |s,v| + f.puts [v[:id],s,v[:value]].join "," + end + end +end + +def create_model t + File.open(t.name,"w+") do |f| + model = Model::LazarClassification.create(training_dataset: Dataset.find(File.read(t.prerequisites.first).chomp)) + f.puts model.id + end +end + +def validate_model t + File.open(t.name,"w+") do |f| + rcv = Validation::RepeatedCrossValidation.create(Model.find(File.read(t.prerequisites.first).chomp)) + f.puts rcv.id + end +end + +def predict t + File.open(t.name,"w+") do |f| + model = Model.find t.prerequisites[0] + dataset = Dataset.find t.prerequisites[1] + prediction = model.predict dataset + f.puts prediction.id + end +end diff --git a/data/PA_complete_SMILES.csv b/data/PA_complete_SMILES.csv deleted file mode 100644 index 378d8c7..0000000 --- a/data/PA_complete_SMILES.csv +++ /dev/null @@ -1,676 +0,0 @@ -ID;CID;Name;SMILES -1;9415;1: Monocrotaline;C[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O -2;5281743;1: Retrosine;C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(CO)O)C -3;73614;"1: Indicine -2: Intermedine -3: Lycopsamine -4: Rinderine -5: Echinatine";C[C@@H]([C@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)O)O -4;119040;1: Trichodesmine;CC(C)[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O -5;280564;1: Indicine N-oxide;C[C@@H]([C@](C(C)C)(C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)O)[O-])O)O -6;5280906;1: Senecionine;C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C -7;5281733;"1: Integerrimine -2: Inegerrimine";C/C=C/1\C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C -8;5281734;"1: Isatidine -2: Retrorsine N-oxide";C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(CO)O)C -9;5281744;1: Riddeliine;C/C=C\1/CC(=C)[C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(CO)O -10;5281756;1: 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-21;442726;"1: Fulvine -2: Crispatine";C[C@@H]1C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC(=O)[C@@H]([C@@]1(C)O)C -22;5281753;"1: Symlandine -2: 7-Angeloylechinatine -3: 7-Angeloylrinderine -4: Echiumine";C/C=C(/C)\C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)O)(C(C)C)O -23;5281754;"1: Symphytine -2: Mycoscorpine -3: 7-Tigloyllacopsamine -4: 7-Tiglyl-9-viridiflorylretronecine";C/C=C(\C)/C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)O)(C(C)C)O -24;6269253;"1: Latifoline -2: Cynoglossum";C/C=C(\C)/C(=O)OC1CCN2C1C(=CC2)COC(=O)C3(C(C(=O)OC3C)C)O -25;6440301;1: Riddelline N-oxide;C/C=C\1/CC(=C)[C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(CO)O -26;6440889;"1: Gynuramine -2: 19-Hydroxysenecionine";C/C=C/1\CC(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O)CO -27;6441178;1: 12,21-Dihydroxy-4-methyl-4,8-secosenecinonan-8,11,16-trione;C[C@@H]1C/C(=C\CO)/C(=O)O[C@@H]2CC[N+]3([C@@]2(C(=CC3)COC(=O)[C@]1(C)O)O)C -28;12308873;1: Erucifoline (Z );C/C=C\1/CC2(C(O2)(C(=O)OCC3=CCN4[C@H]3[C@@H](CC4)OC1=O)C)CO -29;15120074;1: Seneciphyllinine;C/C=C\1/CC(=C)[C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)OC(=O)C -30;15736564;1: Adonifoline;CC1C2(CC3(CO1)C(O3)(C(=O)OCC4=CCN5[C@H]4[C@@H](CC5)OC2=O)C)O -31;76957522;(1R,4Z,6R,7S,14R,17S)-4-ethylidene-7,17-dihydroxy-7-(hydroxymethyl)-6,14-dimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-en-14-ium;C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CC[N@@+]3([C@]2([C@@H](CC3)OC1=O)O)C)(CO)O)C -32;98222;1: Europine;CC(C(C(=O)OCC1=CCN2C1C(CC2)O)(C(C)(C)O)O)OC -33;197173;1: Monocrotaline N-oxide;CC1C(=O)OC2CC[N+]3(C2C(=CC3)COC(=O)C(C1(C)O)(C)O)[O-] -34;259727;"1: Spectabiline -2: Acetylmonocrotaline";C[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@@]1(C)OC(=O)C)(C)O -35;268949;1: Monocrotaline diacetate;C[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@@]1(C)OC(=O)C)(C)OC(=O)C -36;279070;1: Swazine;CC1C(=C)C(=O)OC2CCN3C2C(=CC3)COC(=O)C(C14CO4)(C)O -37;323256;1: Europine N-oxide;CC(C(C(=O)OCC1=CC[N+]2(C1C(CC2)O)[O-])(C(C)(C)O)O)OC -38;333106;1: (7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl)methyl 2-hydroxy-2-phenylbutanoate;CCC(C1=CC=CC=C1)(C(=O)OCC2=CC[N+]3(C2C(CC3)O)[O-])O -39;333468;1: [(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl 2-phenylacetate;C1CN2CC=C([C@@H]2[C@@H]1O)COC(=O)CC3=CC=CC=C3 -40;333469;1: [(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl 3-methylbutanoate;CC(C)CC(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O -41;340066;"1: Intermedine N-oxide -2: Lycopsamine N-oxide -3: Echinatine N-oxide -4: Rinderine N-oxide";C[C@H]([C@@](C(C)C)(C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)O)[O-])O)O -42;341142;1: 4,6,8,9,9a,9b-hexahydro[1,3]dioxepino[4,5,6-gh]pyrrolizine;C1CN2CC=C3C2C1OCOC3 -43;357033;1: [(7R)-7-(ethylcarbamoyloxy)-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl 2-(4-chlorophenyl)-2-hydroxybutanoate;CCC(C1=CC=C(C=C1)Cl)(C(=O)OCC2=CC[N+]3(C2[C@@H](CC3)OC(=O)NCC)[O-])O -44;357034;1: [(7R)-4-oxido-7-(phenylcarbamoyloxy)-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl 2-(4-chlorophenyl)-2-hydroxybutanoate;CCC(C1=CC=C(C=C1)Cl)(C(=O)OCC2=CC[N+]3(C2[C@@H](CC3)OC(=O)NC4=CC=CC=C4)[O-])O -45;5281729;"1: Echimidine -2: Heliosupine -3: Cynoglossofin";C/C=C(/C)\C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)O)(C(C)(C)O)O -46;5458800;1: Lasiocarpine N-oxide;C/C=C(/C)\C(=O)O[C@H]1CC[N+]2([C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)OC)(C(C)(C)O)O)[O-] -47;6438237;"1: Spartioidine -2: Seneciphynine";C/C=C/1\CC(=C)[C@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O -48;6440654;1: Scorpioidine;C/C=C(\C)/C(=O)O[C@@H](C)[C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)O -49;6604611;1: (1R,4E,6S,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;C/C=C/1\C[C@@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(CO)O)C -50;10569934;1: (13R)-13-hydroxyretroisosenine;C[C@@H]1[C@H]([C@@]2(CC(=O)O[C@@H]3CCN4[C@@H]3C(=CC4)COC(=O)[C@]1(O2)C)C)O -51;21771304;1: [(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-phenylbutanoate;CC[C@](C1=CC=CC=C1)(C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)O)O -52;44284782;[(1S,7aR)-1-[(2-hydroxy-2-phenylbutanoyl)oxy]-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl 2-hydroxy-2-phenylbutanoate;CCC(C1=CC=CC=C1)(C(=O)OCC2=CCN3[C@H]2[C@H](CC3)OC(=O)C(CC)(C4=CC=CC=C4)O)O -53;44284870;1-hydroxy-7-{[(2-hydroxy-2-phenylpropanoyl)oxy]methyl}-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;CC(C1=CC=CC=C1)(C(=O)OCC2=CC[N+]3(C2C(CC3)O)[O-])O -54;44374459;(1R)-7-[(benzoyloxy)methyl]-1-hydroxy-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;C1C[N+]2(CC=C(C2[C@@H]1O)COC(=O)C3=CC=CC=C3)[O-] -55;44374601;(1R,7aR)-7-{[(2,3-dihydroxy-2-methylbutanoyl)oxy]methyl}-1-hydroxy-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;CC(C(C)(C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)O)[O-])O)O -56;44559289;1: 7-Acetylscorpioidine;C/C=C(\C)/C(=O)O[C@@H](C)[C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)C)O -57;71449185;1: (1S,7aR)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2S)-2-hydroxy-2-phenylbutanoate;CC[C@](C1=CC=CC=C1)(C(=O)O[C@H]2CCN3[C@@H]2C(=CC3)CO)O -58;71449186;1: (1S,7aR)-1-{[(2S)-2-hydroxy-2-phenylbutanoyl]oxy}-7-(hydroxymethyl)-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;CC[C@](C1=CC=CC=C1)(C(=O)O[C@H]2CC[N+]3([C@@H]2C(=CC3)CO)[O-])O -59;71458133;1: (1S,7aR)-7-{[(2-hydroxy-2-phenylbutanoyl)oxy]methyl}-1-{[(2S)-2-hydroxy-2-phenylbutanoyl]oxy}-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;CC[C@](C1=CC=CC=C1)(C(=O)O[C@H]2CC[N+]3([C@@H]2C(=CC3)COC(=O)C(CC)(C4=CC=CC=C4)O)[O-])O -60;76313095;1: (1S,7aR)-7-({[(2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-1-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;C/C=C(/C)\C(=O)O[C@H]1CC[N+]2([C@@H]1C(=CC2)COC(=O)[C@@]([C@@H](C)OC)(C(C)C)O)[O-] -61;76315880;1: (1R,5R,6R,17R)-5,6,7,7-tetramethyl-4-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;C[C@@H]1[C@H](C(C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC(=O)C1=C)(C)C)C -62;76330453;1: Acetylusaramine;C/C=C/1\C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(COC(=O)C)O)C -63;76334042;"1: Echimidine N-oxide -2: Aspermine N-oxide";C/C=C(/C)\C(=O)O[C@@H]1CC[N+]2([C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)O)(C(C)(C)O)O)[O-] -64;59827875;1: (1R,4Z,17R)-4-ethylidene-7,7-dimethyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;C/C=C\1/CC(=C)C(C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)C -65;91554673;1: (1R,17R)-4-ethylidene-7,7-dimethyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;CC=C1CC(=C)C(C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)C -66;31745;1: 12,18-dihydroxy-13,19-didehydrosenecionan-11,16-dione;CC=C1CC(=C)C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(CO)O -67;33555;1: Acetylheliotrine;CC(C)C(C(C)OC)(C(=O)OCC1=CCN2C1[C@H](CC2)OC(=O)C)O -68;43040;1: 7,9-Di-n-valerylheliotridine;CCCCC(=O)OCC1=CCN2C1[C@H](CC2)OC(=O)CCCC -69;72614;1: Jaconine;C[C@@H]1C[C@@](C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]1(C)O)(C(C)Cl)O -70;107939;1: (1R,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-en-14-ium-14-olate;CC=C1C[C@H]([C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(C)O)C -71;119052;1: Jacozine;C[C@H]1[C@@]2(O1)CC(=C)[C@@](C(=O)OCC3=CCN4[C@H]3[C@@H](CC4)OC2=O)(C)O -72;119390;1: [7-(2-methylbut-2-enoyloxy)-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl 2,3-dihydroxy-2-(1-methoxyethyl)-3-methylbutanoate;CC=C(C)C(=O)OC1CC[N+]2(C1C(=CC2)COC(=O)C(C(C)OC)(C(C)(C)O)O)[O-] -73;148316;1: Retronecine-7:9-(p-chlorobenzoate);C1CN2CC=C([C@@H]2[C@@H]1OC(=O)C3=CC=C(C=C3)Cl)COC(=O)C4=CC=C(C=C4)Cl -74;148317;1: [(7R,8R)-7-(3,4,5-trimethoxybenzoyl)oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl 3,4,5-trimethoxybenzoate;COC1=CC(=CC(=C1OC)OC)C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC(=O)C4=CC(=C(C(=C4)OC)OC)OC -75;148318;1: Retronecine-7,9-piperonylate;C1CN2CC=C([C@@H]2[C@@H]1OC(=O)C3=CC4=C(C=C3)OCO4)COC(=O)C5=CC6=C(C=C5)OCO6 -76;148326;1: Retronecine 7,9-phenylacetate diester;C1CN2CC=C([C@@H]2[C@@H]1OC(=O)CC3=CC=CC=C3)COC(=O)CC4=CC=CC=C4 -77;153499;1: Senecivernine;CC1C(C(C(=O)OCC2=CCN3C2C(CC3)OC(=O)C1=C)(C)O)C -78;156006;"1: Acetyllycopsamine -2: Acetylechinatine -3: Acetlyintermedine -4: Acetylrinderine";C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)C)O)O -79;156038;4,9-dihydroxy-8-methyl-4,9-bis(propan-2-yl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹?,¹?]nonadec-13-ene-3,6,10-trione;CC1C(C(=O)OCC2=CCN3C2C(CC3)OC(=O)C(CC(=O)O1)(C(C)C)O)(C(C)C)O -80;156169;1: Crotananine;CC1C(C(C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC(=O)C1C)O)C -81;156170;Cronaburmine;CC1C(C(=O)OC2CCN3C2C(=CC3)COC(=O)C1C(C)O)C -82;156778;1: Uplandicine;C[C@@H]([C@](C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)C)(C(C)(C)O)O)O -83;157017;1: 7H-(1,5,10)Trioxacyclotetradecino(7,8,9-gh)pyrrolizine-2,5,9(8H)-trione,3,4,11,13,15,16,16a,16b-octahydro-3,4,8-trihydroxy-3-(1-hydroxy-1-methylpropyl)-7-methyl-8-(1-methylethyl)-, (16aR,16bR)-;CCC(C)(C1(C(C(=O)OC(C(C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C(C)C)O)C)O)O)O -84;158192;1: Senecicannabine;C[C@H]1C2(O1)C[C@]3(CO3)[C@@](C(=O)OCC4=CCN5[C@H]4[C@@H](CC5)OC2=O)(C)O -85;162662;1: Retronecine 7,9-bis(p-nitrobenzoate);C1CN2CC=C(C2C1OC(=O)C3=CC=C(C=C3)[N+](=O)[O-])COC(=O)C4=CC=C(C=C4)[N+](=O)[O-] -86;165417;"1: Sceleratin -2: Sceleratine";C[C@@H]1C(C(C(=O)O[C@@H]2CCN3C2C(=CC3)COC(=O)C1(C)O)(CO)O)C -87;165551;1: Retusamine;CCC12C(C(C(=O)OCC3=CC[N+]4(C3(C(CC4)OC1=O)O)C)(OC2=O)C)C -88;167211;1: Retronecine 7,9-isovalerate diester;CC(C)CC(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)CC(C)C -89;169196;1: Crosemperine;C[C@H]1[C@H](C(=O)O[C@@H]2CC[N@+]3([C@@]2(C(=CC3)COC(=O)[C@]1(C)O)O)C)C(C)C -90;169779;1: Emiline;CCC1CC(=C)C(C(=O)OCC2=CC[N+]3(C2([C@@H](CC3)OC1=O)O)C)(C)O -91;179107;1: Latifoline-N-oxide;CCC(C)C(=O)OC1CC[N+]2(C1C(=CC2)COOC(=O)C3=C(OC(=O)C3C)C)[O-] -92;180203;"1: Aucherine -2: Incanine";CC(C)C1C(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O)O -93;180509;1: Uluganine;CC(C)C(C(C)O)(C(=O)OCC1=CCN2C1C(CC2)OC(=O)CC(C)(C)O)O -94;181267;1: 8,12-dihydroxy-4-methyl-11,16-dioxo-15,20-dihydro-15,20-epoxysenecionan-4-ium;CC1CC2(C(O2)C)C(=O)OC3CC[N+]4(C3(C(=CC4)COC(=O)C1(C)O)O)C -95;181871;1: Yamataimine;CC[C@H]1C[C@H]([C@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C -96;181990;1: Bisline;CC[C@]1(C[C@H]([C@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C)O -97;182761;1: (7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl 2,3,4-trimethyl-5-oxooxolane-3-carboxylate;CC1C(=O)OC(C1(C)C(=O)OCC2=CCN3C2C(CC3)O)C -98;186182;1: Retronecine N-ethylcarbamate diester;CCNC(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)NCC -99;186973;1: (1r,7ar)-7-(methoxymethyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl ethylcarbamate;CCNC(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC -100;186974;1: Retronecine 9-(N-ethylcarbamate);CCNC(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O -101;186977;1: 7-{[(2,3-dihydroxy-2-methylbutanoyl)oxy]methyl}-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl 2,3-dihydroxy-2-methylbutanoate;CC(C(C)(C(=O)OCC1=CCN2C1C(CC2)OC(=O)C(C)(C(C)O)O)O)O -102;186980;1: O-Acetylcallimorphine;CCC(C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)C)OC(=O)C -103;187805;Triacetylindicine;CC(C)C(C(C)OC(=O)C)(C(=O)OCC1=CCN2C1C(CC2)OC(=O)C)OC(=O)C -104;188435;1: Retroisosenine;C[C@@H]1C[C@@]2(CC(=O)O[C@@H]3CCN4[C@@H]3C(=CC4)COC(=O)[C@@]1(O2)C)C -105;189677;" -1: Othonnine";CCC1([C@@H](C(C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC1=O)C(C)C)O)O -106;190233;1: 4-hydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2h-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3h)-dione 11-oxide;CC1C(=O)OCC2=CC[N+]3(C2C(CC3)OC(=O)C(C1(C)O)C)[O-] -107;213104;1: Diacetylmonocrotaline;CC1C(=O)OC2CCN3C2C(=CC3)COC(=O)C(C1(C)OC(=O)C)(C)OC(=O)C -108;427386;1: 7-(hydroxymethyl)-4-propyl-2,3,5,8-tetrahydro-1H-pyrrolizin-4-ium-1-ol;CCC[N+]12CCC(C1C(=CC2)CO)O -109;427628;1: 5,6-dihydroxy-4,5,6,13-tetramethyl-3,7-dioxo-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium;CC1C(=O)OC2CC[N+]3(C2C(=CC3)COC(=O)C(C1(C)O)(C)O)C -110;427631;1: 5,6-dihydroxy-4,5,6-trimethyl-3,7-dioxo-13-(prop-2-en-1-yl)-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium;CC1C(=O)OC2CC[N+]3(C2C(=CC3)COC(=O)C(C1(C)O)(C)O)CC=C -111;427636;1: 4-ethyl-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-4-ium-1-ol;CC[N+]12CCC(C1C(=CC2)CO)O -112;428743;1: (7-hydroxy-4-methyl-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl)methyl 2-hydroxy-2-(1-hydroxyethyl)-3-methylbutanoate;CC(C)C(C(C)O)(C(=O)OCC1=CC[N+]2(C1C(CC2)O)C)O -113;442740;"1: Isolycopsamine -2: Tesselatine";C[C@H]([C@](C(C)C)(C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)CO)O)O -114;442742;1: [(7S,8R)-7-(2-methylbut-2-enoyloxy)-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoate;CC=C(C)C(=O)O[C@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)OC)(C(C)(C)O)O -115;494923;1: [7-(2-methylbut-2-enoyloxy)-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl 3-hydroxy-2,4-dimethyl-5-oxooxolane-3-carboxylate;CC=C(C)C(=O)OC1CCN2C1C(=CC2)COC(=O)C3(C(C(=O)OC3C)C)O -116;522876;1: [7-(2-methylbut-2-enoyloxy)-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl 2-(hydroxymethyl)but-2-enoate;CC=C(C)C(=O)OC1CCN2C1C(=CC2)COC(=O)C(=CC)CO -117;610955;1: Indicine pertrimethylsilyl ether;CC(C)C(C(C)O[Si](C)(C)C)(C(=O)OCC1=CCN2C1C(CC2)O[Si](C)(C)C)O[Si](C)(C)C -118;636922;1: Retrohoustine;CC(C)[C@@](C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)O -119;638871;1: [(7R,8S)-7-acetyloxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S,3R,4S)-3-hydroxy-2,4-dimethyl-5-oxooxolane-3-carboxylate;C[C@@H]1C(=O)O[C@H]([C@]1(C(=O)OCC2=CCN3[C@@H]2[C@@H](CC3)OC(=O)C)O)C -120;638872;1: (1R,7aR)-7-[[(Z)-2-Methyl-2-butenoyl]oxymethyl]-2,3,5,7a-tetrahydro-1H-pyrrolizine-1-ol;C/C=C(/C)\C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O -121;3033169;1: 7,9-Dipivalylheliotridine;CC(C)(C)C(=O)OCC1=CCN2[C@H]1[C@H](CC2)OC(=O)C(C)(C)C -122;3038510;"1: (1R,4R,8R)-7-(hydroxymethyl)-4-oxido-2,3,5,8-tetrahydro-1H-pyrrolizin-4-ium-1-ol ";C1C[N@+]2(CC=C([C@@H]2[C@@H]1O)CO)[O-] -123;3080172;1: 9-O-(R(-)-2-(4'-Chlorophenyl)-2-hydroxybutyryl)retronecine N-oxide;CC[C@@](C1=CC=C(C=C1)Cl)(C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)O)[O-])O -124;3085052;"1: Croburhine -2: Crotalarine";CCC1(C(=O)OC2CCN3[C@@H]2C(=CC3)COC(=O)C(C1(C)O)(C)O)C -125;3086069;1: Spiraline;C[C@@H]1[C@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC(=O)[C@]([C@H](C(=O)O1)O)(C(C)C)O)(C(C)C)O -126;3360000;1: O7-Methylretronecine;COCC1=CCN2C1C(CC2)O -127;5036864;1: 4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadeca-5,11-diene-3,8-dione;CC=C1C=C(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O)C -128;5134178;1: (7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl 2-(1-methoxyethyl)-3-methylbutanoate;CC(C)C(C(C)OC)C(=O)OCC1=CCN2C1C(CC2)O -129;5255771;1: 5,6-dihydroxy-6-(hydroxymethyl)-5-methyl-4-(propan-2-yl)-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-ene-3,7-dione;CC(C)C1C(=O)OC2CCN3C2C(=CC3)COC(=O)C(C1(C)O)(CO)O -130;5281721;"1: Rivularine -2: O-7-Angelylheliotridine -3: 7-Angelyretronecine";C/C=C(/C)\C(=O)O[C@H]1CCN2[C@@H]1C(=CC2)CO -131;5318830;1: [(7R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (E)-2-methylbut-2-enoate;C/C=C(\C)/C(=O)OCC1=CCN2C1[C@@H](CC2)O -132;5319875;1: (4R,5R,6S,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-ene-3,7-dione;C[C@H]1C(=O)OC2CCN3[C@@H]2C(=CC3)COC(=O)[C@@]([C@]1(C)O)(C)O -133;5319976;1: [(7R)-7-[(E)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate;C/C=C(\C)/C(=O)O[C@@H]1CCN2C1C(=CC2)COC(=O)[C@@]([C@H](C)O)(C(C)C)O -134;5320165;1: (1R,4E)-4-ethylidene-7-hydroxy-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;C/C=C/1\CC(C(C(=O)OCC2=CCN3C2[C@@H](CC3)OC1=O)O)C -135;5321160;1: (1R,5R)-4,7-dihydroxy-7-(hydroxymethyl)-4,5,6-trimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;C[C@@H]1C(C(C(=O)OCC2=CCN3C2[C@@H](CC3)OC(=O)C1(C)O)(CO)O)C -136;5368830;1: Doriasenine;C/C=C(/CO)\C(=O)OCC1=CCN2C1C(CC2)OC(=O)/C=C(\C)/CO -137;5379437;1: (4E)-5,7-bis(acetyloxy)-4-ethylidene-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-en-14-ium;C/C=C/1\C(C(C(C(=O)OCC2=CC[N+]3(C2(C(CC3)OC1=O)O)C)(C)OC(=O)C)C)OC(=O)C -138;5566367;1: (1R,4Z,7S,17S)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;C/C=C\1/CC(=C)[C@](C(=O)OCC2=CCN3[C@@H]2[C@@H](CC3)OC1=O)(C)O -139;5969895;1: (4E)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;C/C=C/1\CC(=C)C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(CO)O -140;6104648;1: (4E)-4-ethylidene-7-hydroxy-6,7-dimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-en-14-ium-14-olate;C/C=C/1\CC(C(C(=O)OCC2=CC[N+]3(C2C(CC3)OC1=O)[O-])(C)O)C -141;6254547;1: 4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0<14,17>]he ptadeca-5,11-diene-3,8-dione;C/C=C/1\C=C(/C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O)\C -142;6351912;1: (1R,7aR)-7-({[(2R)-2,3-dihydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate;C/C=C(/C)\C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@@H](C)OC)(C(C)(C)O)O -143;6429351;1: 5,6-Dihydro-7,9-dimethoxy-7H-pyrrolizine;COCC1=CCN2C1[C@@H](CC2)OC -144;6429352;1: 7-acetyl-9-(2,3-dihydroxybutyryl) retronecine;CC(C(C(=O)OCC1=CCN2C1[C@@H](CC2)OC(=O)C)O)O -145;6429354;1: 7-acetyl-9-(2-hydroxy-3-methylbutyryl) retronecine;CC(C)C(C(=O)OCC1=CCN2C1[C@@H](CC2)OC(=O)C)O -146;6429355;1: 7-acetyl-9-(2-methylbutyryl) retronecine;CCC(C)C(=O)OCC1=CCN2C1[C@@H](CC2)OC(=O)C -147;6429356;1: 7-Acetylretronecine;CC(=O)O[C@@H]1CCN2C1C(=CC2)CO -148;6431047;1: 3'-Acetylheliosupine;C/C=C(/C)\C(=O)O[C@@H]1CCN2C1C(=CC2)COC(=O)C(C(C)OC(=O)C)(C(C)(C)O)O -149;6431048;1: 7-(2-Methylbutyryl)-9-(2,3-dihydroxybutyryl) retronecine;CCC(C)C(=O)O[C@@H]1CCN2C1C(=CC2)COC(=O)C(C(C)O)O -150;6433648;1: Istidine;C/C=C/1\C[C@H]([C@@](C(=O)OCC2=CC[N+]3(C2[C@@H](CC3)OC1=O)[O-])(CO)O)C -151;6433995;1: Hydroxysenkirkine;C/C=C/1\CC(C(C(=O)OCC2=CC[N+]3(C2(C(CC3)OC1=O)O)C)(CO)O)C -152;6437833;1: (4Z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadeca-4,11-dien-14-ium;CC1/C=C(/C(=O)OC2CC[N+]3(C2(C(=CC3)COC(=O)C1(C)OC(=O)C)O)C)\C=C -153;6437851;1: (1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizinium, 3-ethylidene-2,3,4,5,6,7,9,11,13,14,14a,14b-dodecahydro-6,14b-dihydroxy-5,6,12-trimethyl-2,7-dioxo-, (3Z,5R,6R,14aR,14bS)-(partial)-;C/C=C/1\C[C@H]([C@@](C(=O)OCC2=CC[N+]3([C@]2([C@@H](CC3)OC1=O)O)C)(C)O)C -154;6440495;1: Symphytine oxide;C/C=C(\C)/C(=O)OC1CC[N+]2(C1C(=CC2)COC(=O)C(C(C)C)(C(C)O)O)[O-] -155;6440559;1: 2H-(1,6)Dioxacyclotridecino(2,3,4-gh)pyrrolizine-2,8(5H)-dione,6,7,10,12,14,15,15a,15b-octahydro-7-hydroxy-4,6,7-trimethyl-, (3Z,6R,7R,15aR,15bR)-;C[C@@H]1C/C(=C/C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]1(C)O)/C -156;6440796;"1: Triangularine -2: Triangularicine -3: Neotriangularicine";C/C=C(\C)/C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)/C(=C\C)/CO -157;6440923;1: Epoxyseneciphylline;C/C=C\1/CC2(CO2)C(C(=O)OCC3=CCN4C3C(CC4)OC1=O)(C)O -158;6441608;1: [(7R,8R)-7-[(E)-3-phenylprop-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (E)-3-phenylprop-2-enoate;C1CN2CC=C([C@@H]2[C@@H]1OC(=O)/C=C/C3=CC=CC=C3)COC(=O)/C=C/C4=CC=CC=C4 -159;6442429;1: Cynoglossamine;CC(C)[C@](C(C)OC(=O)/C=C/C1=CC=C(C=C1)O)(C(=O)OCC2=CCN3[C@H]2[C@H](CC3)O)O -160;6442556;1: 9-Angeloylretronecine N-oxide;C/C=C(/C)\C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)O)[O-] -161;6442559;1: (4Z)-5,7-BIS(ACETYLOXY)-4-ETHYLIDENE-17-HYDROXY-6,7,14-TRIMETHYL-3,8-DIOXO-2,9-DIOXA-14-AZATRICYCLO[9.5.1.0(1)?,(1)?]HEPTADEC-11-EN-14-IUM;C/C=C\1/C(C(C(C(=O)OCC2=CC[N+]3(C2(C(CC3)OC1=O)O)C)(C)OC(=O)C)C)OC(=O)C -162;6442619;1: Seneciphylline N-oxide;C/C=C/1\CC(=C)[C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(C)O -163;6443105;"1: [(7R,8R)-7-(ethylcarbamoyloxy)-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (E)-2-methylbut-2-enoate ";CCNC(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)/C(=C/C)/C -164;6556553;1: (1S,4S,5R,6R,16R)-5,6-dihydroxy-5,6-dimethyl-4-(propan-2-yl)-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-ene-3,7-dione;CC(C)[C@@H]1C(=O)O[C@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O -165;6708770;1: (1R,6R,7R)-4-ethylidene-7-hydroxy-7-(2-hydroxyethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;CC=C1C[C@H]([C@@](C(=O)OCC2=CCN3C2[C@@H](CC3)OC1=O)(CCO)O)C -166;7082455;1: (1R,7R,17S)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;CC=C1CC(=C)[C@@](C(=O)OCC2=CCN3[C@@H]2[C@@H](CC3)OC1=O)(C)O -167;7224673;1: (1R,4E,5Z,7S,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadeca-5,11-diene-3,8-dione;C/C=C/1\C=C(/[C@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)\C -168;7457361;1: (1R,8R)-4-benzyl-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-4-ium-1-ol;C1C[N+]2(CC=C([C@@H]2[C@@H]1O)CO)CC3=CC=CC=C3 -169;9548770;1: Senecionan;C/C=C\1/C[C@H]([C@@H](COCC2=CCN3[C@H]2[C@@H](CC3)OC1)C)C -170;9975102;1: (1R,8S)-8-hydroxy-8-(hydroxymethyl)-4,6-dimethylidene-2,10-dioxa-15-azatricyclo[10.5.1.0¹?,¹?]octadec-12-ene-3,9-dione;C=C1CC(=C)C(=O)O[C@@H]2CCN3C2C(=CC3)COC(=O)[C@](C1)(CO)O -171;10023607;1: (1S,7aR)-7-({[2-hydroxy-3-methoxy-2-(propan-2-yl)butanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate;C/C=C(/C)\C(=O)O[C@H]1CCN2[C@@H]1C(=CC2)COC(=O)C(C(C)C)(C(C)OC)O -172;10095536;1: [(1R,7aR)-1-[(3-hydroxy-3-methylbutanoyl)oxy]-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2R)-2-[(1S)-1-(acetyloxy)ethyl]-2-hydroxy-3,3-dimethylbutanoate;C[C@@H]([C@@](C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)CC(C)(C)O)(C(C)(C)C)O)OC(=O)C -173;10251171;1: [(1R,7aR)-1-[(3-hydroxy-3-methylbutanoyl)oxy]-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2R)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3,3-dimethylbutanoate;C[C@@H]([C@@](C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)CC(C)(C)O)(C(C)(C)C)O)O -174;10253491;1: (1S,7aR)-7-({[3-(acetyloxy)-2-hydroxy-2-(2-hydroxypropan-2-yl)butanoyl]oxy}methyl)-1-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;C/C=C(/C)\C(=O)O[C@H]1CC[N+]2([C@@H]1C(=CC2)COC(=O)C(C(C)OC(=O)C)(C(C)(C)O)O)[O-] -175;10412383;1: (1S,7aR)-7-({[3-(acetyloxy)-2-hydroxy-2-(1-methoxyethyl)-3-methylbutanoyl]oxy}methyl)-1-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;C/C=C(/C)\C(=O)O[C@H]1CC[N+]2([C@@H]1C(=CC2)COC(=O)C(C(C)OC)(C(C)(C)OC(=O)C)O)[O-] -176;10548599;1: (1R,5S,6R,7R,8S,18R)-5,7,8-trimethyl-3,9-dioxo-2,10,19-trioxa-15-azatetracyclo[10.5.1.1?,?.0¹?,¹?]nonadec-12-en-6-yl acetate;C[C@@H]1[C@H]([C@@]2(CC(=O)O[C@@H]3CCN4[C@@H]3C(=CC4)COC(=O)[C@]1(O2)C)C)OC(=O)C -177;10569935;1: (1R,5R,7S,8S,18R)-7-hydroxy-5,7,8-trimethyl-2,10,19-trioxa-15-azatetracyclo[10.5.1.1?,?.0¹?,¹?]nonadec-12-ene-3,9-dione;C[C@@]12CC(=O)O[C@@H]3CCN4[C@@H]3C(=CC4)COC(=O)[C@@](O1)([C@@](C2)(C)O)C -178;10572157;1: (1R,5S,6R,16S)-6-(benzyloxy)-5,6-dimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-ene-3,7-dione;C[C@H]1CC(=O)O[C@@H]2CCN3[C@H]2C(=CC3)COC(=O)[C@]1(C)OCC4=CC=CC=C4 -179;10577975;1: [(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S,3R)-2-[(4-methoxyphenyl)methoxy]-2,3-dimethyl-5-oxo-5-[(3-sulfanylpropyl)sulfanyl]pentanoate;C[C@H](CC(=O)SCCCS)[C@@](C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)OCC3=CC=C(C=C3)OC -180;10597940;1: (1R,5R,6S,16R)-6-[(4-methoxyphenyl)methoxy]-5,6-dimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-ene-3,7-dione;C[C@@H]1CC(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@@]1(C)OCC4=CC=C(C=C4)OC -181;10639512;1: 7-Angeloyl-9-(2-methylbutyryl)retronecine;CCC(C)C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)/C(=C\C)/C -182;10696910;1: [(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S,3R)-4-(1,3-dithian-2-ylidene)-2-[(4-methoxyphenyl)methoxy]-2,3-dimethylbutanoate;C[C@H](C=C1SCCCS1)[C@@](C)(C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)O)OCC4=CC=C(C=C4)OC -183;10710914;1: 7-Tigloyl-9-(2-methylbutyryl)retronecine;CCC(C)C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)/C(=C/C)/C -184;10719345;1: [(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S,3R)-2-(benzyloxy)-4-(1,3-dithian-2-ylidene)-2,3-dimethylbutanoate;C[C@H](C=C1SCCCS1)[C@@](C)(C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)O)OCC4=CC=CC=C4 -185;10759513;1: 7-Angeloyl-9-(2,3-dihydroxybutyryl)retronecine;C/C=C(/C)\C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)C(C(C)O)O -186;10838897;1: [(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S,3R)-2-(benzyloxy)-2,3-dimethyl-5-oxo-5-[(3-sulfanylpropyl)sulfanyl]pentanoate;C[C@H](CC(=O)SCCCS)[C@@](C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)OCC3=CC=CC=C3 -187;10938567;1: (2Z,4R,5R)-6-{[(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methoxy}-2-ethylidene-4,5-dimethyl-5-[(methylsulfanyl)methoxy]-6-oxohexanoic acid;C/C=C(/C[C@@H](C)[C@](C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)OCSC)\C(=O)O -188;10939203;1: 1-(benzyloxy)-7-[(benzyloxy)methyl]-4-methyl-7a-(sulfonatooxy)-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium;C[N+]12CCC(C1(C(=CC2)COCC3=CC=CC=C3)OS(=O)(=O)[O-])OCC4=CC=CC=C4 -189;10991752;1: (1R,7aR)-7-{[(tert-butyldimethylsilyl)oxy]methyl}-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate;C/C=C(/C)\C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)CO[Si](C)(C)C(C)(C)C -190;10992912;1: Acetyldulciformine N-oxide;CC[C@H]1C[C@@H]([C@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(C)OC(=O)C)C -191;10996028;1: (1R,7aR)-7-{[(tert-butyldimethylsilyl)oxy]methyl}-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl 1-[2-(trimethylsilyl)ethyl] (2R,3R,4R)-2-[(tert-butyldimethylsilyl)oxy]-2,3,4-trimethyl-5-methylidenehexanedioate;C[C@H]([C@@H](C)[C@](C)(C(=O)OCC[Si](C)(C)C)O[Si](C)(C)C(C)(C)C)C(=C)C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)CO[Si](C)(C)C(C)(C)C -192;11008580;1: methyl (1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizine-7-carboxylate;COC(=O)C1=CCN2[C@H]1[C@@H](CC2)O -193;11011039;1: (1R,7aR)-7-{[(tert-butyldimethylsilyl)oxy]methyl}-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-ol;CC(C)(C)[Si](C)(C)OCC1=CCN2[C@H]1[C@@H](CC2)O -194;11014516;"1: (1R,7aR)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-ol; dibutylstannane";CCCC[Sn]CCCC.C1CN2CC=C([C@@H]2[C@@H]1O)CO -195;11058357;1: (1R,4E,6R,7R,17R)-4-ethylidene-6,7-dimethyl-7-[(methylsulfanyl)methoxy]-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;C/C=C/1\C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)OCSC)C -196;11068907;1: (1R,4S,6S,7S,17R)-4-ethyl-6,7-dimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-en-7-yl acetate;CC[C@H]1C[C@@H]([C@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)OC(=O)C)C -197;11241297;1: [(1S,7aR)-1-(tert-butoxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methanol;CC(C)(C)O[C@H]1CCN2[C@@H]1C(=CC2)CO -198;11436705;1: ethyl (1S,7aR)-1-(tert-butoxy)-2,3,5,7a-tetrahydro-1H-pyrrolizine-7-carboxylate;CCOC(=O)C1=CCN2[C@H]1[C@H](CC2)OC(C)(C)C -199;11522514;1: (S)-2-Hydroxy-2-[(S)-1-hydroxyethyl]-4-methylvaleric acid [(7S,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-yl]methyl ester;C[C@@H]([C@@](CC(C)C)(C(=O)OCC1=CCN2[C@H]1[C@H](CC2)O)O)O -200;11594349;1: (1R,3R,4R,14R)-4-hydroxy-3-methyl-4-(propan-2-yl)-2,6-dioxa-11-azatricyclo[6.5.1.0¹¹,¹?]tetradec-8-en-5-one;C[C@@H]1[C@@](C(=O)OCC2=CCN3[C@H]2[C@H](O1)CC3)(C(C)C)O -201;11618501;1: methyl (1R,7aR)-1-[(1S)-1-[2,4,6-tris(propan-2-yl)phenyl]ethoxy]-2,3,5,7a-tetrahydro-1H-pyrrolizine-7-carboxylate;C[C@@H](C1=C(C=C(C=C1C(C)C)C(C)C)C(C)C)O[C@@H]2CCN3[C@@H]2C(=CC3)C(=O)OC -202;11811349;1: (1R,4Z,6R,7R,17R)-4-ethylidene-6,7-dimethyl-7-[(methylsulfanyl)methoxy]-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)OCSC)C -203;11827237;1: 1-(benzyloxy)-7-[(benzyloxy)methyl]-7a-({[(Z)-[methoxy(oxido)methylidene]amino]sulfonyl}oxy)-4-methyl-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium;C[N+]12CCC(C1(C(=CC2)COCC3=CC=CC=C3)OS(=O)(=O)/N=C(/[O-])\OC)OCC4=CC=CC=C4 -204;11827238;1: 1-(benzyloxy)-7-[(benzyloxy)methyl]-7a-{[(methoxycarbonyl)sulfamoyl]oxy}-4-methyl-2,3,5,7a-tetrahydro-1h-pyrrolizinium;C[N+]12CCC(C1(C(=CC2)COCC3=CC=CC=C3)OS(=O)(=O)NC(=O)OC)OCC4=CC=CC=C4 -205;12085704;1: Leptanthine N-oxide;C[C@H]([C@](C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)O)[O-])(C(C)(C)O)O)O -206;12085705;1: Leptanthine;C[C@H]([C@](C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)(C(C)(C)O)O)O -207;12085706;1: 3'-O-Acetylechihumiline N-oxide;C[C@H]([C@](C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)OC(=O)C=C(C)C)[O-])(C(C)(C)O)O)OC(=O)C -208;12299896;1: (1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;C/C=C\1/C[C@H]([C@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C -209;12308839;1: Hydroxymyoscorpine;C/C=C(\C)/C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@@H](C)O)(C(C)(C)O)O -210;13195112;1: 7-Tigloylretronecine;C/C=C(\C)/C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)CO -211;13258912;1: (1R,4Z,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-en-14-ium-14-olate;C/C=C\1/CC(=C)[C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(C)O -212;14313395;1: [(1R,7aR)-1-{[(2Z)-2-methylbut-2-enoyl]oxy}-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S,3R,4R)-3-hydroxy-2,4-dimethyl-5-oxooxolane-3-carboxylate;C/C=C(/C)\C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@]3([C@H](C(=O)O[C@H]3C)C)O -213;14313398;1: 9-Tigloylretronecine;C/C=C(\C)/C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O -214;14589301;1: (1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl benzoate;C1CN2CC=C(C2C1O)COC(=O)C3=CC=CC=C3 -215;14680172;1: Parsonsianine;CC[C@@]1([C@H](OC(=O)[C@H]([C@@](C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC1=O)(C(C)C)O)O)C)O -216;14825842;1: Eruciflorine;C[C@@H]1C/C(=C\CO)/C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]1(C)O -217;14845641;1: Parsonsianidine;CCC(C)[C@]1([C@H](C(=O)O[C@@H]([C@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(CC)O)C)O)O -218;14845643;1: 17-Methylparsonsianidine;CCC(C)[C@]1([C@H](C(=O)O[C@@H]([C@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C(C)C)O)C)O)O -219;15060933;1: Parsonsine;C[C@@H]1[C@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC(=O)[C@](CC(=O)O1)(C(C)C)O)(C(C)C)O -220;15060936;1: 14-Deoxyparsonsianidine;CCC(C)[C@]1(CC(=O)O[C@@H]([C@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(CC)O)C)O -221;15240755;"1: 3'-Acetylindicine -2: 3'-Acetylsupinine -3: 3'-Acetylechinatine -4: 3'-Acetylrinderine";C[C@@H]([C@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)O)OC(=O)C -222;15286355;1: Echihumiline;C[C@@H]([C@](C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)C=C(C)C)(C(C)(C)O)O)O -223;15286357;"1: 7-Senecioylretronecine -2: 7-Senecioylheliotridine";CC(=CC(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)CO)C -224;15286358;"1: Echiupinine -2: 7-Senecioylrinderine";C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)C=C(C)C)O)O -225;15558714;1: Dicrotaline;CC1(CC(=O)OCC2=CCN3C2C(CC3)OC(=O)C1)O -226;15559784;1: 2,3,5,7a-Tetrahydro-1-hydroxy-1H-pyrrolizine-7-methanol 4-oxide;C1C[N+]2(CC=C(C2C1O)CO)[O-] -227;15765644;1: 3'-Acetylechimidine;C/C=C(\C)/C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)OC(=O)C)(C(C)(C)O)O -228;15765645;"1: 9-Senecioylretronecine ";CC(=CC(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)C -229;15967910;1: (1R,4Z,6R,7R)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-en-14-ium-17-olate;C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CC[N+]3(C2([C@@H](CC3)OC1=O)[O-])C)(C)O)C -230;16687858;1: (7R,12R)-9,9-dibutyl-8,10-dioxa-4-aza-9-stannatricyclo[5.4.1.0?,¹²]dodec-1-ene;CCCC[Sn]1(OCC2=CCN3[C@H]2[C@H](O1)CC3)CCCC -231;20056157;1: (4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-3,7-dioxo-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium-13-olate;C[C@H]1C(=O)OC2CC[N+]3([C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O)[O-] -232;20056173;1: (1R,5R,7R,8S,15S,18R)-15-(chloromethyl)-5,7,8-trimethyl-3,9-dioxo-2,10,19-trioxa-15-azatetracyclo[10.5.1.1?,?.0¹?,¹?]nonadec-12-en-15-ium;C[C@@H]1C[C@@]2(CC(=O)O[C@@H]3CC[N@+]4([C@@H]3C(=CC4)COC(=O)[C@]1(O2)C)CCl)C -233;20106090;1: (1S,7aR)-1-hydroxy-7-[({2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoyl}oxy)methyl]-4-methyl-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium;C[C@H](C(C(C)C)(C(=O)OCC1=CC[N+]2([C@H]1[C@H](CC2)O)C)O)OC -234;20839516;1: (1R,4Z,6S,7S,17R)-4-ethylidene-7-hydroxy-6-(hydroxymethyl)-7-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;C/C=C\1/C[C@H]([C@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)CO -235;21124823;1: (1R)-4-ethyl-6,16-dihydroxy-4,6,13-trimethyl-5-methylidene-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium;CCC1(CO[C@@H]2CC[N+]3(C2(C(=CC3)COCC(C1=C)(C)O)O)C)C -236;21586628;1: (1R,7aR)-1-hydroxy-7-(hydroxymethyl)-4-methyl-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium;C[N+]12CC[C@H]([C@H]1C(=CC2)CO)O -237;21586631;1: (1R,4Z,7R,8R,18R)-8-hydroxy-5,7,8-trimethyl-2,10-dioxa-15-azatricyclo[10.5.1.0¹?,¹?]octadeca-4,12-diene-3,9-dione;C[C@@H]1C/C(=C\C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]1(C)O)/C -238;21606568;1: (1R,4Z,5S,6S,7S)-5,7-bis(acetyloxy)-4-ethylidene-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-en-14-ium-17-olate;C/C=C\1/[C@H]([C@@H]([C@](C(=O)OCC2=CC[N+]3(C2([C@@H](CC3)OC1=O)[O-])C)(C)OC(=O)C)C)OC(=O)C -239;21671366;1: (1R,7aR)-7-[(benzyloxy)methyl]-1-[(2-methoxyethoxy)methoxy]-2,3,5,7a-tetrahydro-1H-pyrrolizine;COCCOCO[C@@H]1CCN2[C@@H]1C(=CC2)COCC3=CC=CC=C3 -240;21671448;1: (1S,7aS)-1-(benzyloxy)-7-[(benzyloxy)methyl]-2,3,5,7a-tetrahydro-1H-pyrrolizine;C1CN2CC=C([C@H]2[C@H]1OCC3=CC=CC=C3)COCC4=CC=CC=C4 -241;21762186;1: tert-butyl (1R,16R)-3,7-dioxo-2,8-dioxa-5,13-diazatricyclo[8.5.1.0¹³,¹?]hexadec-10-ene-5-carboxylate;CC(C)(C)OC(=O)N1CC(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC(=O)C1 -242;21762187;1: (1R,16R)-2,8-dioxa-5,13-diazatricyclo[8.5.1.0¹³,¹?]hexadec-10-ene-3,7-dione;C1CN2CC=C3[C@@H]2[C@@H]1OC(=O)CNCC(=O)OC3 -243;21762188;1: (1R,16R)-5-(3-carboxypropanoyl)-3,7-dioxo-2,8-dioxa-5,13-diazatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium;C1C[NH+]2CC=C3[C@@H]2[C@@H]1OC(=O)CN(CC(=O)OC3)C(=O)CCC(=O)O -244;21762361;1: (1R,16R)-5-[(2-methyl-1,3-dithian-2-yl)methyl]-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-ene-3,7-dione;CC1(SCCCS1)CC2CC(=O)OCC3=CCN4[C@H]3[C@@H](CC4)OC(=O)C2 -245;21762363;1: 2-{[(Z)-{1-[(1R,16R)-3,7-dioxo-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-5-yl]propan-2-ylidene}amino]oxy}acetic acid;C/C(=N/OCC(=O)O)/CC1CC(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC(=O)C1 -246;23305243;1: (4'E)-4'-ethylidene-7'-hydroxy-7'-methyl-2',9'-dioxa-14'-azaspiro[oxirane-2,6'-tricyclo[9.5.1.0¹?,¹?]heptadecan]-11'-ene-3',8'-dione;C/C=C/1\CC2(CO2)C(C(=O)OCC3=CCN4C3C(CC4)OC1=O)(C)O -247;23305253;1: (1R,4Z,6R,7R,17S)-7,17-dihydroxy-4-(2-hydroxyethylidene)-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-en-14-ium;C[C@@H]1C/C(=C/CO)/C(=O)O[C@@H]2CC[N+]3([C@@]2(C(=CC3)COC(=O)[C@]1(C)O)O)C -248;23350898;1: (1R,4E,6R,7S,17R)-4-ethylidene-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene;C/C=C/1\C[C@H]([C@@H](COCC2=CCN3[C@H]2[C@@H](CC3)OC1)C)C -249;23968120;1: Rinderine;CC(C)C(C(C)C)(C(=O)OCC1=CCN2C1C(CC2)O)O -250;26879145;1: (1R,7aR)-1-hydroxy-7-({[(2R)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylbutanoyl]oxy}methyl)-4-methyl-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium;C[C@H]([C@](C(C)C)(C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)O)C)O)O -251;38364109;1: (1R,4S,5S,6S,16R)-4,5-dihydroxy-4,5,6-trimethyl-3,7-dioxo-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium-13-olate;C[C@@H]1C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC(=O)[C@@]([C@@]1(C)O)(C)O)[O-] -252;44374956;1: (1R)-1-hydroxy-7-{[(2-phenylacetyl)oxy]methyl}-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;C1C[N+]2(CC=C(C2[C@@H]1O)COC(=O)CC3=CC=CC=C3)[O-] -253;53462637;1: (16aR,16bR)-3,4,8-trihydroxy-3-(2-hydroxybutan-2-yl)-7-methyl-8-(propan-2-yl)-3,4,11,13,15,16,16a,16b-octahydro-7H-[1,5,10]trioxacyclotetradecino[7,8,9-gh]pyrrolizine-2,5,9(8H)-trione;CCC(C)(C1(C(C(=O)OC(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C(C)C)O)C)O)O)O -254;56776345;1: 4,5-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-ene-3,7-dione;CC1C(=O)OCC2=CCN3C2C(CC3)OC(=O)C(C1(C)O)(C)O -255;71358863;"1: 1H-Pyrrolizine-7-carboxylicacid, 2,3,5,7a-tetrahydro-1-hydroxy-, (1S,7aR)- ";C1CN2CC=C([C@@H]2[C@H]1O)C(=O)O -256;71440312;1: Callimorphine;CCC(C)(C(=O)OCC1=CCN2C1C(CC2)O)OC(=O)C -257;72701752;1: (1S,7aR)-1-hydroxy-7-{[(2,3,4-trihydroxy-2,3-dimethylpentanoyl)oxy]methyl}-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;CC(C(C)(C(C)(C(=O)OCC1=CC[N+]2([C@H]1[C@H](CC2)O)[O-])O)O)O -258;72702799;1: Acetylrinderine N-oxide;C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CC[N+]2([C@H]1[C@H](CC2)OC(=O)C)[O-])O)O -259;72702800;1: (1S,7aR)-1-{[2,3-dihydroxy-2-(propan-2-yl)butanoyl]oxy}-7-({[2,3-dihydroxy-2-(propan-2-yl)butanoyl]oxy}methyl)-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;CC(C)C(C(C)O)(C(=O)OCC1=CC[N+]2([C@H]1[C@H](CC2)OC(=O)C(C(C)C)(C(C)O)O)[O-])O -260;73759932;1: Retronecine, bis(2-methylcrotonate);C/C=C(\C)/C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)/C(=C/C)/C -261;73893110;1: (1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl acetate;CC(=O)OCC1=CCN2C1C(CC2)O -262;73893120;1: [1-(acetyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl acetate;CC(=O)OCC1=CCN2C1C(CC2)OC(=O)C -263;73893122;1: [1-(heptanoyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl heptanoate;CCCCCCC(=O)OCC1=CCN2C1C(CC2)OC(=O)CCCCCC -264;73893125;1: (1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl 2-(2-hydroxy-3,4-dimethyl-5-oxooxolan-2-yl)acetate;CC1C(C(OC1=O)(CC(=O)OCC2=CCN3C2C(CC3)O)O)C -265;78358487;1: Jacoline;C[C@@H]1C[C@@](C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]1(C)O)([C@@H](C)O)O -266;91735634;1: 7-(Acetoxymethyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl tiglate;C/C=C(\C)/C(=O)OC1CCN2C1C(=CC2)COC(=O)C -267;91746708;1: (1'R,2S,3S,6'S,7'R,17'R)-7'-hydroxy-3,7'-dimethyldispiro[oxirane-2,4'-[2,9]dioxa-[14]azatricyclo[9.5.1.0¹?,¹?]heptadecane-6',2''-oxiran]-11'-ene-3',8'-dione;C[C@H]1[C@@]2(O1)C[C@]3(CO3)[C@@](C(=O)OCC4=CCN5[C@H]4[C@@H](CC5)OC2=O)(C)O -268;91746994;1: Acetylerucifoline;C/C=C\1/CC2(C(O2)(C(=O)OCC3=CCN4[C@@H]3[C@H](CC4)OC1=O)C)COC(=O)C -269;91746995;1: Acetylgynuramine;C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)COC(=O)C -270;91746999;1: Erucifoline (E );C/C=C/1\CC2(C(O2)(C(=O)OCC3=CCN4[C@@H]3[C@@H](CC4)OC1=O)C)CO -271;91747008;1: Creatonotine;CC[C@H](C)[C@@H](C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)O -272;91747009;1: Dehydrojaconine;CC([C@]1(CC(=C)[C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)O)Cl -273;91747010;1: Desoxyaxillarine;C[C@H]([C@]1(C[C@@H](C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC1=O)C(C)C)O)O -274;91747011;1: Isocreatonotine;CC(C)[C@H](C(=O)O[C@@H]1CCN2C1C(=CC2)CO)O -275;91747348;1: 7-acetyl-9-curassavoylheliotridine;CCC(C)[C@@]([C@@H](C)O)(C(=O)OCC1=CCN2[C@H]1[C@H](CC2)OC(=O)C)O -276;91747349;1: 7-acetyl-9-sarracinoylretronecine;CC(=CC(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)C)C -277;91747351;1: 7-Diacetylintermedine;C[C@@H]([C@](C(=O)OCC1=CCN2C1[C@@H](CC2)OC(=O)C)(C(C)(C)O)O)OC(=O)C -278;91747352;1: 7-Diacetyllycopsamine;C[C@@H](C(C(C)C)(C(=O)OCC1=CCN2C1[C@@H](CC2)OC(=O)C)O)OC(=O)C -279;91747355;1: 9-Curassavoylheliotridine;CCC(C)[C@@]([C@@H](C)O)(C(=O)OCC1=CCN2[C@H]1[C@H](CC2)O)O -280;91747358;1: Dihydroxytriangularicine;C/C=C(\C)/C(=O)O[C@@H]1CCN2[C@H]1C(=CC2)COC(=O)C(CO)(C(C)O)O -281;91747359;1: Dihydroxytriangularine;C/C=C(/C)\C(=O)O[C@@H]1CCN2C1C(=CC2)COC(=O)C(CO)(C(C)O)O -282;91747605;1: beta.-isovaleryl echinatine;C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@H](CC2)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CC(C)C -283;91747606;1: beta.-tiglyl echinatine;C/C=C(\C)/C(=O)O[C@@H](C)[C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@H](CC2)O[Si](C)(C)C)O[Si](C)(C)C -284;91747608;1: 7-Acetylechinatine;C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@H](CC2)OC(=O)C)O[Si](C)(C)C)O[Si](C)(C)C -285;91747609;1: 7-Angelylechinatine;C/C=C(/C)\C(=O)O[C@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)O[Si](C)(C)C)(C(C)C)O[Si](C)(C)C -286;91747611;1: 7-Tiglylechinatine;C/C=C(\C)/C(=O)O[C@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)O[Si](C)(C)C)(C(C)C)O[Si](C)(C)C -287;91748008;1: 7-Senecioyllycopsamine;C[C@@H]([C@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)O)OC(=O)C=C(C)C -288;91748009;1: Pycnanthine;C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)/C=C(\C)/CO)O)O -289;91748011;1: 7-Angeloyl-9-(2,3-dihydroxylbutyryl)heliotridine;C/C=C(\C)/C(=O)O[C@H]1CCN2[C@@H]1C(=CC2)COC(=O)C(C(C)O)O -290;91748012;1: 7-Angeloyl-9-(2-methylbutyryl)heliotridine;CCC(C)C(=O)OCC1=CCN2[C@H]1[C@H](CC2)OC(=O)/C(=C/C)/C -291;91749686;1: 7-Tigloyl-9-dihydroxysenecioylretronecine;C/C=C(\C)/C(=O)O[C@@H]1CCN2C1C(=CC2)COC(=O)C(C(C)(C)O)O -292;91749687;1: 9-Angeloylanacrotine;C/C=C\1/C[C@@H]([C@](C(=O)OCC2=CCN3C2[C@H](CC3)OC1=O)(C)OC(=O)/C(=C\C)/C)C -293;91749688;1: 9-Hydroxyheptanoylretronecine;CCCCCCC(=O)OCC1=CCN2C1[C@@H](CC2)O -294;91749690;1: 9-Isosenecioylretronecine;CC(=C)CC(=O)OCC1=CCN2C1[C@@H](CC2)O -295;91749691;1: Acetylsenecivernine;C[C@H]1[C@H]([C@](C(=O)OCC2=CCN3C2[C@H](CC3)OC(=O)C1=C)(C)OC(=O)C)C -296;91749692;1: Methylmonocrotaline;C[C@]1(C(=O)OCC2=CCN3C2[C@H](CC3)OC(=O)C([C@]1(C)O)(C)C)O -297;91751310;1: 3'-Acetylechiupinine;C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)C=C(C)C)O)OC(=O)C -298;91751311;1: 3'-Acetylmyoscorpine;C/C=C(\C)/C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)OC(=O)C)(C(C)C)O -299;91751312;1: 3'-Benzoylindicine;C[C@@H]([C@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)O)OC(=O)C3=CC=CC=C3 -300;91751313;1: 3'-cis-Cinnamoylindicine;C[C@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@@H]1[C@H](CC2)O)O)OC(=O)/C=C\C3=CC=CC=C3 -301;91751314;1: 3'-Dihydrocinnamoylindicine;C[C@@H]([C@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)O)OC(=O)CCC3=CC=CC=C3 -302;91751316;1: 7-Propionylintermedine;CCC(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)O)(C(C)C)O -303;91751437;1: [(1S,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl 3-methylbut-2-enoate;CC(=CC(=O)OCC1=CCN2[C@H]1[C@H](CC2)O)C -304;91752775;1: (5R,9Z,12R,18R)-9-ethylidene-5,7-dimethyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0?,?.0¹?,¹?]octadec-1(17)-ene-4,10-dione;C/C=C\1/CC2([C@@](O2)(C(=O)OCC3=CCN4[C@H]3[C@@H](CC4)OC1=O)C)C -305;91752874;1: 7-(1H-Pyrrol-2-yloxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-ol;C1CN2CC=C(C2C1O)COC3=CC=CN3 -306;91752876;1: [7-(Hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-yl] 1H-pyrrole-3-carboxylate;COCC1=CCN2C1C(CC2)OC(=O)C3=CNC=C3 -307;91752877;1: [(7R)-7-Hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl hexanoate;CCCCCC(=O)OCC1=CCN2C1[C@@H](CC2)O -308;91753270;1: Grahamine;CCC(C)C(=O)OC1(C(C(=O)OC2CCN3C2C(=CC3)COC(=O)C1(C)O)C)C -309;91753274;1: Pumiline A;CC(C)[C@@H]1C(=O)O[C@@H]2CCN3C2C(=CC3)COC(=O)[C@]([C@@]14CO4)(C)O -310;91753673;"1: 8-Epineosarracine -2: 8-Episarracine";C/C=C(/C)\C(=O)O[C@H]1CCN2[C@H]1C(=CC2)COC(=O)C=C(C)C -311;92167309;1: (1R,7aS)-1-hydroxy-7-(hydroxymethyl)-4-(prop-2-en-1-yl)-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium;C=CC[N+]12CC[C@H]([C@@H]1C(=CC2)CO)O -312;92170778;1: (1R,7aS)-1-hydroxy-7-({[(2R)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;C[C@H]([C@](C(C)C)(C(=O)OCC1=CC[N+]2([C@@H]1[C@@H](CC2)O)[O-])O)OC -313;92240481;1: [(1R,7aS)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylbutanoate;C[C@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@@H]1[C@@H](CC2)O)O)O -314;92245581;1: (1R,7aS)-1-hydroxy-7-({[(2R)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylbutanoyl]oxy}methyl)-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;C[C@H]([C@](C(C)C)(C(=O)OCC1=CC[N+]2([C@@H]1[C@@H](CC2)O)[O-])O)O -315;92245583;1: (1R,7aS)-1-hydroxy-7-({[(2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoyl]oxy}methyl)-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CC[N+]2([C@@H]1[C@@H](CC2)O)[O-])O)O -316;92245889;1: (1R,4S,5S,6S,16R)-5,6-dihydroxy-4,5,6-trimethyl-3,7-dioxo-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium-13-olate;C[C@@H]1C(=O)O[C@@H]2CC[N+]3([C@@H]2C(=CC3)COC(=O)[C@@]([C@@]1(C)O)(C)O)[O-] -317;92245890;1: (1R,4R,5S,6S,16R)-5,6-dihydroxy-4,5,6-trimethyl-3,7-dioxo-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium-13-olate;C[C@H]1C(=O)O[C@@H]2CC[N+]3([C@@H]2C(=CC3)COC(=O)[C@@]([C@@]1(C)O)(C)O)[O-] -318;92245891;1: (1S,4S,5S,6S,16R)-5,6-dihydroxy-4,5,6-trimethyl-3,7-dioxo-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium-13-olate;C[C@@H]1C(=O)O[C@H]2CC[N+]3([C@@H]2C(=CC3)COC(=O)[C@@]([C@@]1(C)O)(C)O)[O-] -319;92245892;1: (1S,4R,5S,6S,16R)-5,6-dihydroxy-4,5,6-trimethyl-3,7-dioxo-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium-13-olate;C[C@H]1C(=O)O[C@H]2CC[N+]3([C@@H]2C(=CC3)COC(=O)[C@@]([C@@]1(C)O)(C)O)[O-] -320;92254804;1: (1R,7aR)-7-({[(2R)-2,3-dihydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-1-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;C/C=C(/C)\C(=O)O[C@@H]1CC[N+]2([C@@H]1C(=CC2)COC(=O)[C@@]([C@@H](C)OC)(C(C)(C)O)O)[O-] -321;92258314;1: (1R,4S,5S,6S,16R)-5,6-dihydroxy-4,5,6,13-tetramethyl-3,7-dioxo-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium;C[C@@H]1C(=O)O[C@@H]2CC[N+]3([C@@H]2C(=CC3)COC(=O)[C@@]([C@@]1(C)O)(C)O)C -322;92258315;1: (1R,4R,5S,6S,16R)-5,6-dihydroxy-4,5,6,13-tetramethyl-3,7-dioxo-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium;C[C@H]1C(=O)O[C@@H]2CC[N+]3([C@@H]2C(=CC3)COC(=O)[C@@]([C@@]1(C)O)(C)O)C -323;92258316;1: (1S,4S,5S,6S,16R)-5,6-dihydroxy-4,5,6,13-tetramethyl-3,7-dioxo-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium;C[C@@H]1C(=O)O[C@H]2CC[N+]3([C@@H]2C(=CC3)COC(=O)[C@@]([C@@]1(C)O)(C)O)C -324;92258317;1: (1S,4R,5S,6S,16R)-5,6-dihydroxy-4,5,6,13-tetramethyl-3,7-dioxo-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-en-13-ium;C[C@H]1C(=O)O[C@H]2CC[N+]3([C@@H]2C(=CC3)COC(=O)[C@@]([C@@]1(C)O)(C)O)C -325;92258329;1: (1R,7aS)-4-ethyl-1-hydroxy-7-(hydroxymethyl)-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium;CC[N+]12CC[C@H]([C@@H]1C(=CC2)CO)O -326;94908779;1: (1'R,2S,5'R,7'S,17'R)-7'-hydroxy-5',7'-dimethyl-4'-methylidene-2',9'-dioxa-14'-azaspiro[oxirane-2,6'-tricyclo[9.5.1.0¹?,¹?]heptadecan]-11'-ene-3',8'-dione;C[C@@H]1C(=C)C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@@]([C@@]14CO4)(C)O -327;100854393;1: (1R,4S,5S,6S,16R)-4,5-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-10-ene-3,7-dione;C[C@@H]1C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC(=O)[C@@]([C@@]1(C)O)(C)O -328;100925967;1: Acetylduciformine;CC[C@H]1C[C@H]([C@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)OC(=O)C)C -329;100979629;1: 12-(tert-Butyldimethylsiloxy)-14-methyl-21-norsenecionan-11,16-dione;C[C@@H]1C(C(=C)C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]1(C)O[Si](C)(C)C(C)(C)C)C -330;100979630;1: 9,12-Bis(tert-butyldimethylsiloxy)-10-[1-(trimethylsilyl)ethyl]-14-methyl-21-nor-9,10-secosenecionan-11,16-dione;C[C@H](C(C)C(=C)C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)CO[Si](C)(C)C(C)(C)C)[C@](C)(C(=O)OC(C)[Si](C)(C)C)O[Si](C)(C)C(C)(C)C -331;100979631;1: 9-Hydroxy-12-(tert-butyldimethylsiloxy)-10-[1-(trimethylsilyl)ethyl]-14-methyl-21-nor-9,10-secosenecionan-11,16-dione;C[C@H](C(C)C(=C)C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)CO)[C@](C)(C(=O)OC(C)[Si](C)(C)C)O[Si](C)(C)C(C)(C)C -332;101134822;1: Junceine;CC(C)C1C[C@]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(CO)O)(C)O -333;101244775;1: (2S,3S)-2,3-Dihydroxy-2-ethylbutanoic acid [(7R)-7beta-hydroxy-5,6,7,7aalpha-tetrahydro-3H-pyrrolizine-1-yl]methyl ester;CC[C@]([C@H](C)O)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)O -334;101244776;1: 2,3-Dihydroxy-2-ethylbutanoic acid (1R)-7-(hydroxymethyl)-2,3,5,7abeta-tetrahydro-1H-pyrrolizine-1alpha-yl ester;CCC(C(C)O)(C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)CO)O -335;101286187;1: (1R,4R,7aS)-1,7a-dihydroxy-7-(hydroxymethyl)-4-methyl-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium;C[N@+]12CC[C@H]([C@]1(C(=CC2)CO)O)O -336;101288094;1: Pentanedioic acid 1-[(1R)-2,3,5,7abeta-tetrahydro-1alpha-hydroxy-1H-pyrrolizin-7-yl]methyl 5-(2,2,2-trichloroethyl) ester;C1CN2CC=C([C@@H]2[C@@H]1O)COC(=O)CCCC(=O)OCC(Cl)(Cl)Cl -337;101289784;1: Crotastriatine;C/C=C/1\C[C@H]([C@H](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)OC(=O)C)C -338;101339003;1: Aspermine;C/C=C(\C)/C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@]([C@H](C)O)(C(C)(C)O)O -339;101339004;1: 7-Acetyllycopsamine N-oxide;C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)OC(=O)C)[O-])O)O -340;101339005;1: Uplandicine N-oxide;CC(C(C(=O)OCC1=CC[N+]2(C1C(CC2)OC(=O)C)[O-])(C(C)(C)O)O)O -341;101339006;"1: Echiumine N-oxide -2: Symlandine N-oxide";C/C=C(/C)\C(=O)O[C@@H]1CC[N+]2([C@@H]1C(=CC2)COC(=O)[C@@]([C@@H](C)O)(C(C)C)O)[O-] -342;101360987;1: (2S,3S)-2,3-Dihydroxy-2-isopropylbutanoic acid [(1R)-2,3,5,7abeta-tetrahydro-7-(hydroxymethyl)-1H-pyrrolizine 4-oxide]-1alpha-yl ester;C[C@@H]([C@@](C(C)C)(C(=O)O[C@@H]1CC[N+]2([C@@H]1C(=CC2)CO)[O-])O)O -343;101526911;1: Acetylsenecionin;C/C=C/1\C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)OC(=O)C)C -344;101602684;1: Heliospathine;CCC(C)C(C(C)O)(C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)CO)O -345;101605596;1: 12-Seco-14-deoxyparsonsianine-13-methyl ester;CC[C@]([C@@H](C)O)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)[C@](CC(=O)OC)(C(C)C)O)O -346;101609673;1: Myoscorpine N-oxide;C/C=C(\C)/C(=O)O[C@@H]1CC[N+]2([C@@H]1C(=CC2)COC(=O)[C@@]([C@@H](C)O)(C(C)C)O)[O-] -347;101609674;1: Echiupinine-N-oxide;C[C@H]([C@@](C(C)C)(C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)OC(=O)C=C(C)C)[O-])O)O -348;101613210;1: Ideamine A N-oxide;CC[C@]([C@H](C)O)(C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)O)[O-])O -349;101613211;1: Parsonsine 4-oxide;C[C@@H]1[C@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC(=O)[C@](CC(=O)O1)(C(C)C)O)[O-])(C(C)C)O -350;101616166;1: Ideamine B N-oxide;CC[C@@]1([C@@H](OC(=O)C[C@@](C(=O)O[C@@H]2CC[N+]3([C@@H]2C(=CC3)COC1=O)[O-])(C(C)C)O)C)O -351;101635998;1: 13-O-Acetyldicrotaline;CC(=O)O[C@]1(CC(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC(=O)C1)C -352;101648301;"1: (2R,3S)-2-Isopropyl-2,3-bis[(trimethylsilyl)oxy]butanoic acid [[(1R)-2,3,5,7abeta-tetrahydro-1alpha-[(trimethylsilyl)oxy]-1H-pyrrolizin]-7-yl]methyl ester ";C[C@@H]([C@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C -353;101664189;1: 16-Deoxyparsonsianidine N-oxide;CCC(C)[C@]1(CC(=O)O[C@@H]([C@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(CC)O)C)O -354;101674026;1: Lithosenine;C[C@@H]([C@@](C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)CC(C)(C)O)(C(C)(C)O)O)O -355;101674027;1: Acetyllithosenine;C[C@@H]([C@@](C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)CC(C)(C)O)(C(C)(C)O)O)OC(=O)C -356;101696510;1: (1R,7aR)-7-({[(2R)-2,3-dihydroxy-2-(1-hydroxyethyl)-3-methylbutanoyl]oxy}methyl)-1-{[(2E)-4-hydroxy-3-methylbut-2-enoyl]oxy}-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;CC([C@](C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)OC(=O)/C=C(\C)/CO)[O-])(C(C)(C)O)O)O -357;101705400;1: [(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2Z)-2-(hydroxymethyl)but-2-enoate;C/C=C(/CO)\C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O -358;101705715;1: Neotriangularicine;C/C=C(\C)/C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)/C(=C/C)/CO -359;101779180;1: Crotalanan;C/C=C/1\CO[C@@H]2CCN3[C@@H]2C(=CC3)COC[C@H]([C@@H]1C)C -360;101915797;1: 5'-Acetyllasiocarpine;C/C=C(/C)\C(=O)O[C@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)OC)(C(C)(C)OC(=O)C)O -361;101915798;1: 7-Acetyleuropine;C[C@@H]([C@](C(=O)OCC1=CCN2C1[C@H](CC2)OC(=O)C)(C(C)(C)O)O)OC -362;101915799;1: 5'-Acetyllasiocarpine N-oxide;C/C=C(/C)\C(=O)O[C@H]1CC[N+]2([C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)OC)(C(C)(C)OC(=O)C)O)[O-] -363;101949642;1: Merenskine;C[C@@H]1[C@H]([C@](C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]1(C)O)(CCl)O)C -364;102004942;"1: Ligularine -2: Crotafoline";C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CC[N+]3(C2([C@@H](CC3)OC1=O)[O-])C)(CO)O)C -365;102064908;3'-Acetylindicine N-oxide;C[C@@H]([C@](C(C)C)(C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)O)[O-])O)OC(=O)C -366;102090418;1: Crobarbatine;C[C@H]1CC(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]1(C)O -367;102092537;1: (12S)-12-Hydroxyretroisosenine;C[C@]12CC(=O)O[C@@H]3CCN4[C@@H]3C(=CC4)COC(=O)[C@](O1)([C@@](C2)(C)O)C -368;102115589;1: (1S)-1-hydroxy-4-{[(1S)-1-hydroxy-2,3-dihydro-1H-pyrrolizin-7-yl]methyl}-7-({[2-hydroxy-3-methoxy-2-(propan-2-yl)butanoyl]oxy}methyl)-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium;CC(C)C(C(C)OC)(C(=O)OCC1=CC[N+]2(C1[C@H](CC2)O)CC3=C4[C@H](CCN4C=C3)O)O -369;102115628;1: Anadoline;C/C=C(\C)/C(=O)OCC(C)[C@@H]([C@@H](C)C(=O)OCC1=CC[N+]2([C@H]1[C@@H](CC2)O)[O-])O -370;102122201;1: 2'-Acetylheliotrine;C[C@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@H](CC2)O)OC(=O)C)OC -371;102144111;1: Seneciphyllinine N-oxide;C/C=C/1\CC(=C)[C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(C)OC(=O)C -372;102207572;1: 5'-O-Acetylechimidine;C/C=C(/C)\C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)O)(C(C)(C)OC(=O)C)O -373;102228697;1: 2,3-Dihydroxy-2-(1-methylethyl)butanoic acid [[1-(2-isopropyl-2,3-dihydroxybutanoyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizine 4-oxide]-7-yl]methyl ester;CC(C)C(C(C)O)(C(=O)OCC1=CC[N+]2(C1C(CC2)OC(=O)C(C(C)C)(C(C)O)O)[O-])O -374;102228698;1: (2S,3R)-2,3-Dihydroxy-2-(1-methylethyl)butanoic acid [[(1R,7aS)-1alpha-acetoxy-2,3,5,7a-tetrahydro-1H-pyrrolizine 4-oxide]-7-yl]methyl ester;C[C@H]([C@@](C(C)C)(C(=O)OCC1=CC[N+]2([C@@H]1[C@@H](CC2)OC(=O)C)[O-])O)O -375;102228699;1: 2,3,4-Trihydroxy-2,3-dimethylvaleric acid [[1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizine 4-oxide]-7-yl]methyl ester;CC(C(C)(C(C)(C(=O)OCC1=CC[N+]2(C1C(CC2)O)[O-])O)O)O -376;102445396;1: (1R,4R,6R,7S,17R)-4-[(1R)-1-chloroethyl]-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadec-11-ene-3,8-dione;C[C@@H]1C[C@@](C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]1(CO)O)([C@@H](C)Cl)O -377;102478913;1: (7R,8R)-Petranine;C/C=C(/C)\C(=O)OCC1=CC[N+]23[C@H]1[C@H](CC2)OC3 -378;102588230;1: 2'',3''-Epoxyechiumine;CC1C(O1)(C)C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@@]([C@@H](C)O)(C(C)C)O -379;118701696;1: (4S,8R,9S)-4,9-dihydroxy-8-methyl-4,9-bis(propan-2-yl)-2,7,11-trioxa-16-azatricyclo[11.5.1.0¹?,¹?]nonadec-13-ene-3,6,10-trione;C[C@@H]1[C@](C(=O)OCC2=CCN3C2C(CC3)OC(=O)[C@](CC(=O)O1)(C(C)C)O)(C(C)C)O -380;5380224;1: Heleurine;C[C@H]([C@](C(C)C)(C(=O)OCC1=CCN2[C@H]1CCC2)O)OC -381;442706;"1: Cynaustine -2: Supinine -3: Coromandalinine";C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1CCC2)O)O -382;32319;1: Supinine N-oxide;C[C@@H](C(C(C)C)(C(=O)OCC1=CC[N@+]2(C1CCC2)[O-])O)O -383;158633;1: Curassavinine;CCC(C)C(C(C)O)(C(=O)OCC1=CCN2C1CCC2)O -384;190040;1: Heleurine N-oxide;C[C@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1CCC2)OC(=O)C)OC(=O)C -385;5352405;1: (2-{[(2E)-2-methylbut-2-enoyl]oxy}-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl (2E)-2-methylbut-2-enoate;C/C=C(\C)/C(=O)OCC1=CCN2C1CC(C2)OC(=O)/C(=C/C)/C -386;11723103;1: (7aS)-7-({[2-hydroxy-3-methoxy-2-(propan-2-yl)butanoyl]oxy}methyl)-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium-4-olate;CC(C)C(C(C)OC)(C(=O)OCC1=CC[N+]2([C@H]1CCC2)[O-])O -387;91747534;1: (7aS)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-ylmethyl (2E)-but-2-enoate;C/C=C/C(=O)OCC1=CCN2[C@H]1CCC2 -388;91747615;1: (7aS)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-ylmethyl (2S)-3-methyl-2-[(trimethylsilyl)oxy]-2-[(1R)-1-[(trimethylsilyl)oxy]ethyl]butanoate;C[C@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1CCC2)O[Si](C)(C)C)O[Si](C)(C)C -389;101044824;1: Ilamine;C[C@H]([C@](C(=O)OCC1=CCN2[C@H]1CCC2)(C(C)(C)O)O)OC -390;101044825;1: Ilamine N-oxide;C[C@H]([C@](C(=O)OCC1=CC[N+]2([C@H]1CCC2)[O-])(C(C)(C)O)O)OC -391;5281720;"1: Anacrotine -2: Crotalaburnine";C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H]([C@@H](C3)O)OC1=O)(C)O)C -392;5459074;"1: Madurensine ";C/C=C/1\C[C@H]([C@@](C(=O)OCC2=CCN3C2[C@@H]([C@@H](C3)OC1=O)O)(C)O)C -393;5281752;"1: Senkirkine -2: Neosenkirkine -3: Renardine -4: Syneilesine";C/C=C\1/C[C@H]([C@@](C(=O)OC/C/2=C/CN(CC[C@H](C2=O)OC1=O)C)(C)O)C -394;5284440;"1: Fukinotoxin -2: Petasitenine -3: Ot(h)osenine -4: Tomentosine";C[C@@H]1CC2([C@H](O2)C)C(=O)O[C@@H]3CCN(C/C=C(\C3=O)/COC(=O)[C@]1(C)O)C -395;5281740;1: Otonecine;CN1CC[C@H](C(=O)/C(=C\C1)/CO)O -396;6441254;1: Acetylanonamine;C[C@@H]1C/C(=C\COC(=O)C)/C(=O)O[C@@H]2CCN(C/C=C(\C2=O)/COC(=O)[C@]1(C)O)C -397;22310115;1: (4S,6R,7S,11Z)-4-hydroxy-4-(1-hydroxyethyl)-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate;C[C@@H]1C[C@@](C(=O)OC2CCN(C/C=C(\C2=O)/COC(=O)[C@@]1(C)OC(=O)C)C)(C(C)O)O -398;12041879;1: (1R,4Z,6R,7S,11Z)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6,14-dimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione;C/C=C\1/C[C@H]([C@@](C(=O)OC/C/2=C/CN(CC[C@H](C2=O)OC1=O)C)(CO)O)C -399;44559774;1: (1R,4E,6R,7R,11Z)-7-hydroxy-4-(2-hydroxyethylidene)-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione;C[C@@H]1C/C(=C\CO)/C(=O)O[C@@H]2CCN(C/C=C(\C2=O)/COC(=O)[C@]1(C)O)C -400;59827871;1: (1R,3'R,4R,6S,11Z)-3',6,7,7,14-pentamethyl-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-ene-3,8,17-trione;C[C@H]1C[C@@]2([C@H](O2)C)C(=O)O[C@@H]3CCN(C/C=C(\C3=O)/COC(=O)C1(C)C)C -401;119243;1: (1R,3'S,4S,6R,7R)-7-hydroxy-3',6,7,14-tetramethyl-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-ene-3,8,17-trione;C[C@@H]1C[C@]2([C@@H](O2)C)C(=O)O[C@@H]3CCN(CC=C(C3=O)COC(=O)[C@]1(C)O)C -402;526538;"1: 4,8-Secosenecionan-8,11,16-trione, 12-(acetyloxy)-4-methyl- ";CC=C1CC(C(C(=O)OCC2=CCN(CCC(C2=O)OC1=O)C)(C)OC(=O)C)C -403;3713463;"1: 4,7-dihydroxy-4-(1-hydroxyethyl)-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione ";CC1CC(C(=O)OC2CCN(CC=C(C2=O)COC(=O)C1(C)O)C)(C(C)O)O -404;4095226;1: (4-ethenyl-6,6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadeca-4,11-dien-7-yl) acetate;CC(=O)OC1(C(=O)OCC2=CCN(CCC(C2=O)OC(=O)C(=CC1(C)C)C=C)C)C -405;5281726;1: Doronine;C[C@@H]1C[C@@](C(=O)O[C@@H]2CCN(C/C=C(\C2=O)/COC(=O)[C@]1(C)OC(=O)C)C)([C@@H](C)Cl)O -406;5284370;1: Clivoline;C[C@@H]1/C=C(\C(=O)O[C@@H]2CCN(C/C=C(\C2=O)/COC(=O)[C@@]1(C)OC(=O)C)C)/C=C -407;6324941;1: [(4Z,6R,7S,11Z)-4-ethenyl-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadeca-4,11-dien-7-yl] acetate;C[C@@H]1/C=C(\C(=O)OC2CCN(C/C=C(\C2=O)/COC(=O)[C@@]1(C)OC(=O)C)C)/C=C -408;6428023;1: Acetylsenkirkine;C/C=C\1/C[C@@H]([C@](C(=O)OC/C/2=C/CN(CC[C@@H](C2=O)OC1=O)C)(C)OC(=O)C)C -409;6440206;1: Neopetasitenine;C[C@@H]1C[C@@]2([C@H](O2)C)C(=O)O[C@@H]3CCN(C/C=C(\C3=O)/COC(=O)[C@]1(C)OC(=O)C)C -410;6440207;"1: Ligularidine -2: O-Acetylcrotavernine";C/C=C/1\C[C@H]([C@](C(=O)OC/C/2=C/CN(CC[C@H](C2=O)OC1=O)C)(C)OC(=O)C)C -411;6440919;1: Dihydroclivorine;CC/C/1=C/[C@H]([C@](C(=O)OC/C/2=C/CN(CC[C@H](C2=O)OC1=O)C)(C)OC(=O)C)C -412;6440920;1: Neoligularidine;C/C=C\1/C[C@H]([C@](C(=O)OC/C/2=C/CN(CC[C@H](C2=O)OC1=O)C)(C)OC(=O)C)C -413;6440921;1: Ligularizine;C[C@@H]1CC2([C@H](O2)C)C(=O)O[C@@H]3CCN(C/C=C(\C3=O)/COC(=O)[C@@]1(C)OC(=O)C)C -414;6441405;1: Floradanin;C[C@@H]1CC(C(=O)O[C@@H]2CCN(C/C=C(\C2=O)/COC(=O)[C@]1(C)OC(=O)C)C)(C(C)O)O -415;6442432;"1: Desacetyldoronine -2: Otonecin-jaconine";C[C@@H]1C[C@](C(=O)O[C@@H]2CCN(C/C=C(\C2=O)/COC(=O)[C@]1(C)O)C)(C(C)Cl)O -416;10880125;1: [(6R)-6-(acetyloxy)-1-methyl-5-oxo-1,2,5,6,7,8-hexahydroazocin-4-yl]methyl acetate;CC(=O)OC/C/1=C/CN(CC[C@H](C1=O)OC(=O)C)C -417;11111309;1: 4-(benzyloxy)-6-[(benzyloxy)methyl]-1-methyl-1,2,3,4,5,8-hexahydroazocin-5-one;CN1CCC(C(=O)/C(=C\C1)/COCC2=CC=CC=C2)OCC3=CC=CC=C3 -418;12304138;1: Crosemperine;CC1C(C(=O)O[C@@H]2CCN(C/C=C(\C2=O)/COC(=O)C1(C)O)C)C(C)C -419;14313730;1: Senkirkine N-Oxide;C/C=C\1/C[C@H]([C@@](C(=O)OC/C/2=C/C[N+](CC[C@H](C2=O)OC1=O)(C)[O-])(C)O)C -420;21606532;1: (1R,4Z,5S,6S,7S,11Z)-7-(acetyloxy)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-5-yl acetate;C/C=C\1/[C@H]([C@@H]([C@](C(=O)OC/C/2=C/CN(CC[C@H](C2=O)OC1=O)C)(C)OC(=O)C)C)OC(=O)C -421;21627985;1: (1R,4S,6R,7R,11Z)-4-hydroxy-4-(1-hydroxyethyl)-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate;C[C@@H]1C[C@@](C(=O)O[C@@H]2CCN(C/C=C(\C2=O)/COC(=O)[C@]1(C)OC(=O)C)C)(C(C)O)O -422;89233061;1: [(6R)-6-methoxy-1-methyl-5-oxo-1,2,5,6,7,8-hexahydroazocin-4-yl]methyl (3S)-4-[(2S)-2-(hydroxymethyl)-3-methyloxiran-2-yl]-2,2,3-trimethylbutanoate;CC1[C@](O1)(C[C@H](C)C(C)(C)C(=O)OC/C/2=C/CN(CC[C@H](C2=O)OC)C)CO -423;91746989;"1: Florosenine -2: Otonecine-acetyljacobine -3: Neopetasitenine -4: Ligularizidine";C[C@@H]1C[C@@]2([C@@H](O2)C)C(=O)O[C@H]3CCN(C/C=C(\C3=O)/COC(=O)[C@@]1(C)OC(=O)C)C -424;91747000;"1: Floricaline -2: Otonecine-diacetyljacoline";C[C@H]1C[C@](C(=O)O[C@H]2CCN(C/C=C(\C2=O)/COC(=O)[C@@]1(C)OC(=O)C)C)(C(C)OC(=O)C)O -425;91747001;"1: Floridanine -2: Otonecine-acetyljacoline";C[C@H]1C[C@](C(=O)O[C@H]2CCN(C/C=C(\C2=O)/COC(=O)[C@@]1(C)OC(=O)C)C)([C@H](C)O)O -426;91753267;1: Croaegyptine;CC1C(C(C(=O)OC/C/2=C/CN(CC[C@@H](C2=O)OC1=O)C)(C)O)C -427;91753269;1: Desethylretusamine;CC1C2C(=O)O[C@H]3CCN(C/C=C(\C3=O)/COC(=O)C1(OC2=O)C)C -428;91753273;1: O-Crotaverrine;C/C=C/1\C[C@@H]([C@@](C(=O)OC/C/2=C/CN(CC[C@@H](C2=O)OC1=O)C)(C)O)C -429;91753275;1: (1S,11Z,18R)-4-ethyl-7,14,18-trimethyl-2,6,9-trioxa-14-azatricyclo[9.5.1.1?,?]octadec-11-ene-3,5,8,17-tetrone;CCC12[C@H](C(C(=O)OC/C/3=C/CN(CC[C@@H](C3=O)OC1=O)C)(OC2=O)C)C -430;100925969;1: Hodgsonine;C[C@H]1/C=C(/C(=O)O[C@@H]2CCN(C/C=C(\C2=O)/COC(=O)[C@@]1(C)OC(=O)C)C)\C(C)O -431;101057317;1: (1S,4E,5S,6S,7S,11Z)-7-(acetyloxy)-4-ethylidene-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-5-yl acetate;C/C=C/1\[C@H]([C@@H]([C@](C(=O)OC/C/2=C\CN(CC[C@@H](C2=O)OC1=O)C)(C)OC(=O)C)C)OC(=O)C -432;101096098;1: 4-Ethenyl-6,7,14-trimethyl-7-acetoxy-2,9-dioxa-14-azabicyclo[9.5.1]heptadeca-4,11-diene-3,8,17-trione;CC1/C=C(\C(=O)OC2CCN(C/C=C(/C2=O)\COC(=O)C1(C)OC(=O)C)C)/C=C -433;101297578;1: Crotafoline;C/C=C/1\CC(C(C(=O)OC/C/2=C\CN(CC[C@H](C2=O)OC1=O)C)O)C -434;101360988;1: 12-Acetoxysenkirkine;C/C=C\1/C[C@H]([C@@](C(=O)OC/C/2=C\CN(CC[C@H](C2=O)OC1=O)C)(C)OC(=O)C)C -435;101543954;1: (1R,4R,5S,6R)-4-Isopropyl-5,5-(epoxymethano)-6-hydroxy-6,13-dimethyl-2,8-dioxa-13-azabicyclo[8.5.1]hexadeca-10-ene-3,7,16-trione;CC(C)[C@H]1C(=O)O[C@@H]2CCN(C/C=C(\C2=O)/COC(=O)[C@]([C@@]13CO3)(C)O)C -436;102059844;1: Onetine;C[C@@H]1C[C@@](C(=O)O[C@@H]2CCN(C/C=C(/C2=O)\COC(=O)[C@]1(C)O)C)([C@@H](C)O)O -437;102496937;1: Crotavitelin;C[C@@H]1CC(=O)[C@@]2([C@]1(C(=O)OC/C/3=C/CN(CCC(C3=O)OC2=O)C)C)C -438;102502161;1: (2R,3R)-2-[(2R,3R)-4-[[(6R)-5-Oxo-6-hydroxy-1-methyl-1-azacyclooctane-3-ene-4-yl]methoxy]-2,3-dimethyl-3-hydroxy-4-oxobutyl]-3-methyloxirane-2-carboxylic acid methyl ester;C[C@@H]1[C@](O1)(C[C@@H](C)[C@](C)(C(=O)OC/C/2=C/CN(CC[C@H](C2=O)O)C)O)C(=O)OC -439;104764;1: Dehydromonocrotaline;C[C@H]1C(=O)O[C@@H]2CCN3C2=C(COC(=O)[C@]([C@]1(C)O)(C)O)C=C3 -440;5281742;1: Platyphylline;C/C=C\1/C[C@H]([C@@](C(=O)OC[C@H]2CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C -441;5281746;1: Sarracine;C/C=C(/C)\C(=O)O[C@@H]1CCN2[C@@H]1[C@H](CC2)COC(=O)/C(=C\C)/CO -442;5281748;1: Senaetnine;C/C=C\1/C[C@H]([C@@](C(=O)OCC2=C3[C@H](CC(=O)N3C=C2)OC1=O)(C)OC(=O)C)C -443;6440870;1: Dehydroretrorsine;C/C=C\1/C[C@H]([C@@](C(=O)OCC2=C3[C@@H](CCN3C=C2)OC1=O)(CO)O)C -444;6441180;1: Dehydroanacrotine;C/C=C/1\C[C@H]([C@@](C(=O)OCC2=C3[C@@H]([C@@H](CN3C=C2)O)OC1=O)(C)O)C -445;168571;1: Monocrotaline, alpha-epoxide;CC1C(=O)OC2CCN3C2C4(COC(=O)C(C1(C)O)(C)O)C(C3)O4 -446;355833;1: 7-(-)-Trachelanthylplatynecine;C[C@@H]([C@](C(C)C)(C(=O)OC1CCN2C1C(CC2)CO)O)O -447;5799962;1: Sarracine N-oxide;C/C=C(\C)/C(=O)OC1CC[N+]2(C1C(CC2)COC(=O)/C(=C/C)/CO)[O-] -448;38350;1: Platynecine-7,9-senecioate;CC(=CC(=O)OC[C@H]1CCN2[C@H]1[C@@H](CC2)OC(=O)C=C(C)C)C -449;148320;1: [(1R,7S,8S)-7-(1,3-benzodioxole-5-carbonyloxy)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl 1,3-benzodioxole-5-carboxylate;C1CN2CC[C@@H]([C@@H]2[C@@H]1COC(=O)C3=CC4=C(C=C3)OCO4)OC(=O)C5=CC6=C(C=C5)OCO6 -450;148321;1: [(1S,7R,8R)-7-(3,4,5-trimethoxybenzoyl)oxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl 3,4,5-trimethoxybenzoate;COC1=CC(=CC(=C1OC)OC)C(=O)OC[C@H]2CCN3[C@H]2[C@@H](CC3)OC(=O)C4=CC(=C(C(=C4)OC)OC)OC -451;148322;1: Platynecine 7,9-isovalerate diester;CC(C)CC(=O)OC[C@H]1CCN2[C@H]1[C@@H](CC2)OC(=O)CC(C)C -452;151347;1: Platynecine 7,9-phenylacetate diester;C1CN2CC[C@H]([C@H]2[C@H]1COC(=O)CC3=CC=CC=C3)OC(=O)CC4=CC=CC=C4 -453;151555;" -1: Platynecine 7,9-acetate diester";CC(=O)OC[C@H]1CCN2[C@@H]1[C@H](CC2)OC(=O)C -454;156034;1: 2H-(1,6)Dioxacycloundecino(2,3,4-gh)pyrrolizine-2,6(3H)-dione,decahydro-4-hydroxy-3,4,5-trimethyl-, (8aR,13aR,13bR)-;CC1C(=O)OCC2CCN3C2C(CC3)OC(=O)C(C1(C)O)C -455;162396;1: Platynecine-7:9-(p-nitrobenzoate);C1CN2CCC(C2C1COC(=O)C3=CC=C(C=C3)[N+](=O)[O-])OC(=O)C4=CC=C(C=C4)[N+](=O)[O-] -456;178760;1: Thymidine, 2-O-(2,3-dihydro-7-(hydroxymethyl)-1H-pyrrolizin-1-yl)-, (R)-;CC1=CN(C(=NC1=O)OC2CCN3C2=C(C=C3)CO)[C@H]4C[C@@H]([C@H](O4)CO)O -457;188434;1: Bulgarsenine;C[C@@H]1CC(=CC(=O)O[C@@H]2CCN3[C@@H]2[C@H](CC3)COC(=O)[C@]1(C)O)C -458;194088;1: Disenecioyldehydroretronecine;CC(=CC(=O)OCC1=C2[C@@H](CCN2C=C1)OC(=O)C=C(C)C)C -459;232738;1: {7-[(2-methylbut-2-enoyl)oxy]-4-oxidohexahydro-1H-pyrrolizin-1-yl}methyl 2-(hydroxymethyl)but-2-enoate;CC=C(C)C(=O)OC1CC[N+]2(C1C(CC2)COC(=O)C(=CC)CO)[O-] -460;382065;1: [(1S,7R)-7-(2-methylbut-2-enoyloxy)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl 2-(hydroxymethyl)but-2-enoate;CC=C(C)C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)C(=CC)CO -461;419279;1: 5,6-dihydroxy-5,6,7-trimethyl-4,8-dioxo-13-(trifluoroacetyl)-3,9,16-trioxa-13-azatetracyclo[8.6.1.0¹,¹?.0¹³,¹?]heptadecan-13-ium;CC1C(=O)OC2CC[N+]3(C2C4(COC(=O)C(C1(C)O)(C)O)C(C3)O4)C(=O)C(F)(F)F -462;442746;"1: Nemorensine -2: Mulgediifoline";CC1C[C@@]2(CC(=O)O[C@@H]3CCN4[C@@H]3[C@H](CC4)COC(=O)[C@@]1(O2)C)C -463;442749;1: Parsonsine;C[C@@H]1[C@H](CC(=O)OC[C@H]2CCN3[C@H]2[C@@H](CC3)OC(=O)[C@](CC(=O)O1)(C(C)C)O)C(C)C -464;496831;1: Methyl 7-benzoyloxy-2-hydroxy-3-oxo-1,2,5,6,7,8-hexahydropyrrolizine-1-carboxylate;COC(=O)C1C2C(CCN2C(=O)C1O)OC(=O)C3=CC=CC=C3 -465;526539;1: 8-hydroxy-5,7,8-trimethyl-2,10-dioxa-15-azatricyclo[10.5.1.0¹?,¹?]octadec-4-ene-3,9-dione;CC1CC(=CC(=O)OC2CCN3C2C(CC3)COC(=O)C1(C)O)C -466;4484072;1: 4-ethylidene-6,7-dimethyl-3,8,15-trioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadeca-11(17),12-dien-7-yl acetate;CC=C1CC(C(C(=O)OCC2=C3C(CC(=O)N3C=C2)OC1=O)(C)OC(=O)C)C -467;4484073;1: [5-acetyloxy-7-(2-methylbut-2-enoyloxy)-6,7-dihydro-5H-pyrrolizin-1-yl]methyl 2-(3-methylbut-2-enoyloxymethyl)but-2-enoate;CC=C(C)C(=O)OC1CC(N2C1=C(C=C2)COC(=O)C(=CC)COC(=O)C=C(C)C)OC(=O)C -468;5232043;1: 7-hydroxy-4-methoxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadecane-3,8-dione;CC1CC(C(=O)OC2CCN3C2C(CC3)COC(=O)C1(C)O)OC -469;5281722;1: Angularine;C/C=C\1/CC(=C)[C@@](C(=O)OC[C@H]2[C@@H](CN3[C@H]2[C@@H](CC3)OC1=O)O)(C)O -470;5281745;1: Rosmarinine;C/C=C\1/C[C@H]([C@@](C(=O)OC[C@H]2[C@@H](CN3[C@H]2[C@@H](CC3)OC1=O)O)(C)O)C -471;5281749;"1: Senampeline A -2: Senampeline F";C/C=C(\C)/C(=O)O[C@@H]1C[C@@H](N2C1=C(C=C2)COC(=O)/C(=C/C)/COC(=O)C=C(C)C)OC(=O)C -472;5320938;1: (1R,4R,5S,6R,10S,16R)-6-hydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadecane-3,7-dione;C[C@@H]1[C@@H]([C@@](C(=O)OC[C@H]2CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C -473;5321137;1: [7-[(E)-2-methylbut-2-enoyl]oxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl (E)-2-(hydroxymethyl)but-2-enoate;C/C=C(\C)/C(=O)OC1CCN2C1C(CC2)COC(=O)/C(=C/C)/CO -474;5352420;"1: Neosarracine -2: Neosarrine";C/C=C(/C)\C(=O)OC1CCN2C1C(CC2)COC(=O)/C(=C/C)/CO -475;5916866;1: 2,12-dihydroxy-1,2-dihydrosenecionan-11,16-dione;C/C=C/1\CC(C(C(=O)OCC2C(CN3C2C(CC3)OC1=O)O)(C)O)C -476;6124067;1: (4Z)-4-ethylidene-6,7-dimethyl-3,8,15-trioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadeca-11(17),12-dien-7-yl acetate;C/C=C\1/CC(C(C(=O)OCC2=C3C(CC(=O)N3C=C2)OC1=O)(C)OC(=O)C)C -477;6428018;1: 7,9-Ditigloylplatynecine;C/C=C(\C)/C(=O)OC[C@H]1CCN2C1[C@@H](CC2)OC(=O)/C(=C/C)/C -478;6428020;1: 7-Tigloylplatynecine;C/C=C(\C)/C(=O)O[C@@H]1CCN2C1[C@H](CC2)CO -479;6428026;1: 7-Angeloylplatynecine;C/C=C(/C)\C(=O)O[C@@H]1CCN2C1[C@H](CC2)CO -480;6428030;1: Sarranicine;C/C=C(\C)/C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)/C(=C\C)/CO -481;6429060;1: 7-angeloyl-9-(2,3-dihydroxy propanoyl) retronecine;C/C=C(/C)\C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)C(CO)O -482;6429061;1: 7-Angeloyl-9-(hydroxypropenoyl) retronecine;C/C=C(/C)\C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)C(=C)O -483;6429062;1: 7-Tigloyl-9-(2,3-dihydroxy propanoyl) retronecine;C/C=C(\C)/C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)C(CO)O -484;6429063;1: 7-Tigoyl-9-(hydroxypropenoyl) retronecine;C/C=C(\C)/C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)C(=C)O -485;6440039;1: Platynecine 7,9-cinnamate diester;C1CN2CC[C@H]([C@H]2[C@H]1COC(=O)/C=C/C3=CC=CC=C3)OC(=O)/C=C/C4=CC=CC=C4 -486;6441496;1: Dehydrosenecionine;C/C=C/1\C[C@H]([C@@](C(=O)OCC2=C3[C@@H](CCN3C=C2)OC1=O)(C)O)C -487;6442293;1: 12-O-Acetylrosmarinine;C/C=C\1/C[C@H]([C@@](C(=O)OC[C@H]2[C@@H](CN3[C@H]2[C@@H](CC3)OC1=O)OC(=O)C)(C)O)C -488;6442685;"1: Senampelin D -2: Senampeline D";C/C=C(\C)/C(=O)OC/C(=C/C)/C(=O)OCC1=C2[C@@H](C[C@@H](N2C=C1)OC(=O)C)OC(=O)/C(=C/C)/C -489;6442687;1: [(5S,7R)-5-acetyloxy-7-[(E)-2-methylbut-2-enoyl]oxy-6,7-dihydro-5H-pyrrolizin-1-yl]methyl (E)-2-[[(E)-2-methylbut-2-enoyl]oxymethyl]but-2-enoate;C/C=C(\C)/C(=O)OC/C(=C\C)/C(=O)OCC1=C2[C@@H](C[C@@H](N2C=C1)OC(=O)C)OC(=O)/C(=C/C)/C -490;6445133;1: Dehydrolasiocarpine;C/C=C(\C)/C(=O)O[C@H]1CCN2C1=C(C=C2)COC(=O)[C@@]([C@H](C)OC)(C(C)(C)O)O -491;6912281;"1: Neoplatyphylline -2: Ligularinine";C/C=C/1\C[C@H]([C@@](C(=O)OC[C@H]2CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C -492;10086314;1: Methyl (1S,7R,7aS)-7-(benzoyloxy)-3-oxo-hexahydro-1H-pyrrolizine-1-carboxylate;COC(=O)[C@H]1CC(=O)N2[C@@H]1[C@@H](CC2)OC(=O)C3=CC=CC=C3 -493;10344513;1: Methyl (1S,2R,7S,7aR)-7-(benzoyloxy)-2-{[(2S)-2-methoxy-2-phenylacetyl]oxy}-3-oxo-hexahydro-1H-pyrrolizine-1-carboxylate;CO[C@@H](C1=CC=CC=C1)C(=O)O[C@@H]2[C@H]([C@@H]3[C@H](CCN3C2=O)OC(=O)C4=CC=CC=C4)C(=O)OC -494;10433214;1: [(1S,7R,7aR)-7-{[(2Z)-2-methylbut-2-enoyl]oxy}-hexahydro-1H-pyrrolizin-1-yl]methyl (2Z)-2-{[(3-hydroxy-3-methylbutanoyl)oxy]methyl}but-2-enoate;C/C=C(/C)\C(=O)O[C@@H]1CCN2[C@@H]1[C@H](CC2)COC(=O)/C(=C\C)/COC(=O)CC(C)(C)O -495;10497165;1: (1R,4Z,7S,8S,12S,18R)-8-hydroxy-5,7,8-trimethyl-2,10-dioxa-15-azatricyclo[10.5.1.0¹?,¹?]octadec-4-ene-3,9-dione;C[C@H]1C/C(=C\C(=O)O[C@@H]2CCN3[C@@H]2[C@H](CC3)COC(=O)[C@@]1(C)O)/C -496;10502318;1: (1R,5R,7R,8S,12S,15R,18R)-15-(chloromethyl)-5,7,8-trimethyl-3,9-dioxo-2,10,19-trioxa-15-azatetracyclo[10.5.1.1?,?.0¹?,¹?]nonadecan-15-ium;C[C@@H]1C[C@@]2(CC(=O)O[C@@H]3CC[N@+]4([C@@H]3[C@H](CC4)COC(=O)[C@]1(O2)C)CCl)C -497;10572291;1: (1R,5S,6R,16R)-6-(benzyloxy)-5,6-dimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadecane-3,7-dione;C[C@H]1CC(=O)O[C@@H]2CCN3[C@@H]2C(CC3)COC(=O)[C@]1(C)OCC4=CC=CC=C4 -498;10717096;1: (1R,4Z,7R,8R,12S,18R)-15-(chloromethyl)-8-hydroxy-5,7,8-trimethyl-3,9-dioxo-2,10-dioxa-15-azatricyclo[10.5.1.0¹?,¹?]octadec-4-en-15-ium;C[C@@H]1C/C(=C\C(=O)O[C@@H]2CC[N+]3([C@@H]2[C@H](CC3)COC(=O)[C@]1(C)O)CCl)/C -499;10738499;1: (1R,4Z,7R,8R,12S,18R)-5,7,8-trimethyl-3,9-dioxo-2,10-dioxa-15-azatricyclo[10.5.1.0¹?,¹?]octadec-4-en-8-yl acetate;C[C@@H]1C/C(=C\C(=O)O[C@@H]2CCN3[C@@H]2[C@H](CC3)COC(=O)[C@]1(C)OC(=O)C)/C -500;10739462;1: (1R,4Z,7R,8R,12S,18R)-8-(acetyloxy)-5,7,8-trimethyl-3,9-dioxo-2,10-dioxa-15-azatricyclo[10.5.1.0¹?,¹?]octadec-4-en-15-ium-15-olate;C[C@@H]1C/C(=C\C(=O)O[C@@H]2CC[N+]3([C@@H]2[C@H](CC3)COC(=O)[C@]1(C)OC(=O)C)[O-])/C -501;10787656;1: Callosine;C[C@@H]1C/C(=C\C(=O)O[C@@H]2CCN3[C@@H]2[C@H](C[C@@H]3CC(=O)OC)COC(=O)[C@]1(C)O)/C -502;11233017;1: (1R,7S,7aR)-1-(benzyloxy)-7-[(benzyloxy)methyl]-hexahydro-1H-pyrrolizine;C1CN2CC[C@H]([C@H]2[C@H]1COCC3=CC=CC=C3)OCC4=CC=CC=C4 -503;11303112;1: (1R,2R,7S,7aR)-2-hydroxy-7-(oxan-2-yloxy)-hexahydro-1H-pyrrolizine-1-carboxylic acid;C1CCOC(C1)O[C@H]2CCN3[C@@H]2[C@H]([C@H](C3)O)C(=O)O -504;11369281;1: (1R)-2beta-Hydroxy-7alpha-tert-butoxy-2,3,5,6,7,7aalpha-hexahydro-1H-pyrrolizine-1beta-carboxylic acid ethyl ester;CCOC(=O)[C@H]1[C@H](CN2[C@H]1[C@H](CC2)OC(C)(C)C)O -505;14287858;1: Dehydroriddelliine;C/C=C/1\CC(=C)[C@@](C(=O)OCC2=C3[C@@H](CCN3C=C2)OC1=O)(CO)O -506;14589311;1: (3R,4S,5R,6R)-1-Aza-3-phenyl-4-[[(tert-butyldimethylsilyl)oxy]methyl]-6-hydroxybicyclo[3.3.0]octane-4-carboxylic acid gamma-lactone;CC(C)(C)[Si](C)(C)OC[C@]12[C@H](CN3[C@H]1[C@@H](CC3)OC2=O)C4=CC=CC=C4 -507;14589313;1: (3R,4S,5R,6R)-1-Aza-3-phenyl-4-(benzoyloxymethyl)-6-hydroxybicyclo[3.3.0]octane-4-carboxylic acid gamma-lactone;C1CN2C[C@@H]([C@]3([C@@H]2[C@@H]1OC3=O)COC(=O)C4=CC=CC=C4)C5=CC=CC=C5 -508;14659818;1: (1S,7aalpha)-1beta-[[(E)-2-(Hydroxymethyl)-2-butenoyl]oxymethyl]-7beta-[[(Z)-2-methyl-2-butenoyl]oxy]hexahydro-1H-pyrrolizine 4-oxide;C/C=C(/C)\C(=O)O[C@@H]1CC[N+]2([C@@H]1[C@H](CC2)COC(=O)/C(=C/C)/CO)[O-] -509;16082455;1: (1S,7abeta)-Hexahydro-6alpha,7beta-di(methoxymethoxy)-1H-pyrrolizine-1beta,2alpha,3beta-tricarboxylic acid 3-ethyl 1,2-dimethyl ester;CCOC(=O)[C@@H]1[C@H]([C@@H]([C@@H]2N1C[C@@H]([C@H]2OCOC)OCOC)C(=O)OC)C(=O)OC -510;21144858;1: [2-({[7-(methoxycarbonyl)-7-(phenylselanyl)-hexahydro-1H-pyrrolizin-1-yl]oxy}methyl)phenyl]azinic acid;COC(=O)C1(CCN2C1C(CC2)OCC3=CC=CC=C3[NH+](O)[O-])[Se]C4=CC=CC=C4 -511;21581303;1: (1R,4Z,7S,8S,12S,18R)-8-hydroxy-5,7,8-trimethyl-3,9-dioxo-2,10-dioxa-15-azatricyclo[10.5.1.0¹?,¹?]octadec-4-en-15-ium;C[C@H]1C/C(=C\C(=O)O[C@@H]2CC[NH+]3[C@@H]2[C@H](CC3)COC(=O)[C@@]1(C)O)/C -512;21626760;1: (1S,7S,7aS)-1-{[2-(trimethylsilyl)ethoxy]methoxy}-7-({[2-(trimethylsilyl)ethoxy]methoxy}methyl)-hexahydro-1H-pyrrolizine;C[Si](C)(C)CCOCOC[C@H]1CCN2[C@@H]1[C@H](CC2)OCOCC[Si](C)(C)C -513;21670206;1: (1S,2R,6R,7R,7aR)-6,7-Di-tert-butoxy-2-hydroxy-3-oxohexahydro-1H-pyrrolizine-1-carboxylic acid methyl ester;CC(C)(C)O[C@@H]1CN2[C@@H]([C@H]1OC(C)(C)C)[C@@H]([C@H](C2=O)O)C(=O)OC -514;22524559;1: Neoangularine;C/C=C/1\CC(=C)[C@@](C(=O)OC[C@H]2[C@@H](CN3[C@H]2[C@@H](CC3)OC1=O)O)(C)O -515;23305279;1: (1R,4E,6R,7R,11S,12S,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadecan-12-yl acetate;C/C=C/1\C[C@H]([C@@](C(=O)OC[C@H]2[C@@H](CN3[C@H]2[C@@H](CC3)OC1=O)OC(=O)C)(C)O)C -516;44148183;"1: Senampeline E -2: Senampeline G";C/C=C(\C)/C(=O)OC/C(=C\C)/C(=O)OCC1=C2C(CC(N2C=C1)OC(=O)C)OC(=O)/C(=C/C)/C -517;46861355;1: (15Z)-12-hydroxy-8-methyl-1,2-dihydrosenecionan-11,16-dione;C/C=C\1/CC(C(C(=O)OCC2CCN3C2(C(CC3)OC1=O)C)(C)O)C -518;51413602;1: (1R,4E,6S,7S,11S,17R)-4-ethylidene-6,7-dimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadecan-14-ium;C/C=C/1\C[C@@H]([C@@H](C(=O)OC[C@H]2CC[NH+]3[C@H]2[C@@H](CC3)OC1=O)C)C -519;52340564;1: (1R,6R,7S,11R,17S)-4-ethylidene-7-hydroxy-6,7,17-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadecan-14-ium;CC=C1C[C@H]([C@](C(=O)OC[C@@H]2CC[NH+]3[C@@]2([C@@H](CC3)OC1=O)C)(C)O)C -520;52340565;1: (1R,6R,7S,11R,17S)-4-ethylidene-7-hydroxy-6,7,17-trimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadecane-3,8-dione;CC=C1C[C@H]([C@](C(=O)OC[C@@H]2CCN3[C@@]2([C@@H](CC3)OC1=O)C)(C)O)C -521;68380175;1: (5Z)-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹?]hexadec-5-ene-3,7-dione;C1CN2CCC3C2C1COC(=O)/C=C\CC(=O)O3 -522;74934296;1: 3-{[3-(acetyloxy)-1-[(2-methylbut-2-enoyl)oxy]-2,3-dihydro-1H-pyrrolizin-7-yl]methoxy}-2-ethylidene-3-oxopropyl 2-methylbut-2-enoate;CC=C(C)C(=O)OCC(=CC)C(=O)OCC1=C2C(CC(N2C=C1)OC(=O)C)OC(=O)C(=CC)C -523;91746536;1: [(1S,7R)-7-{[(2E)-2-methylbut-2-enoyl]oxy}-hexahydro-1H-pyrrolizin-1-yl]methyl (2E)-4-hydroxy-3-methylbut-2-enoate;C/C=C(\C)/C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)/C=C(\C)/CO -524;91746606;1: (1S,6S,7S,11S,12R,17S)-7-hydroxy-12-methoxy-5,6,7-trimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadecane-3,8-dione;C[C@H]1C(CC(=O)O[C@H]2CCN3[C@H]2[C@@H](COC(=O)[C@@]1(C)O)[C@H](C3)OC)C -525;91747012;1: (1S,4R,8R,9S,14R)-4-hydroxy-8-methyl-4,9-bis(propan-2-yl)-2,7,12-trioxa-17-azatricyclo[12.5.1.0¹?,²?]icosane-3,6,11-trione;C[C@@H]1[C@@H](CC(=O)OC[C@@H]2CCN3C2[C@H](CC3)OC(=O)[C@@](CC(=O)O1)(C(C)C)O)C(C)C -526;91747610;1: 7-Angelylechinatine;C/C=C(/C)\C(=O)O[C@H]1CCN2[C@@H]1[C@H](CC2)COC(=O)[C@@]([C@H](C)O[Si](C)(C)C)(C(C)C)O[Si](C)(C)C -527;91747612;1: 7-Tiglylechinatine;C/C=C(\C)/C(=O)O[C@H]1CCN2[C@@H]1[C@H](CC2)COC(=O)[C@@]([C@H](C)O[Si](C)(C)C)(C(C)C)O[Si](C)(C)C -528;91747938;1: 7-Senecioylplatynecine;CC(=CC(=O)O[C@@H]1CCN2[C@@H]1[C@H](CC2)CO)C -529;91747943;1: 9-O-Senecioylplatynecine;CC(=CC(=O)OC[C@H]1CCN2[C@H]1[C@@H](CC2)OC(=O)C)C -530;91749424;1: Ipanguline D6;C1CN2CC[C@@H](C2[C@@H]1CO)OC(=O)CC3=CC=CC=C3 -531;91749426;1: Ipanguline A1;C[C@@H]([C@@](C)(C(=O)OC[C@H]1CCN2C1[C@@H](CC2)OC(=O)CC3=CC=CC=C3)O)O -532;91749427;1: Ipanguline A2;C[C@@H]([C@@](C)(C(=O)OC[C@H]1CCN2C1[C@@H](CC2)OC(=O)CC3=CC=CC=C3)O)OC(=O)C -533;91749428;1: Ipanguline A3;C[C@@H]([C@@](C)(C(=O)OC[C@H]1CCN2C1[C@@H](CC2)OC(=O)CC3=CC=CC=C3)OC(=O)C)OC(=O)C -534;91749429;1: Ipanguline A4;CCC(C)C(=O)O[C@@H](C)[C@@](C)(C(=O)OC[C@H]1CCN2C1[C@@H](CC2)OC(=O)CC3=CC=CC=C3)O -535;91749431;1: Ipanguline B2;C[C@@H]([C@@](C)(C(=O)OC[C@H]1CCN2C1[C@@H](CC2)OC(=O)C3=CC=CC=C3O)O)OC(=O)C -536;91749432;1: Ipanguline B3;C[C@@H]([C@@](C)(C(=O)OC[C@H]1CCN2C1[C@@H](CC2)OC(=O)C3=CC=CC=C3O)OC(=O)C)OC(=O)C -537;91749433;1: Ipanguline C1;CCC(C)C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)[C@](C)([C@H](C)O)O -538;91749434;1: Ipanguline C2;CCC(C)C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)[C@](C)([C@H](C)OC(=O)C)O -539;91749435;1: Ipanguline C3;CCC(C)C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)[C@](C)([C@H](C)OC(=O)C)OC(=O)C -540;91749436;1: Ipanguline C4;CCC(C)C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)[C@](C)([C@H](C)OC(=O)C(C)CC)O -541;91749439;1: Ipanguline D12;C[C@@H]([C@@](C)(C(=O)O[C@@H]1CCN2C1[C@H](CC2)CO)O)O -542;91749440;1: Ipanguline D13;C/C=C(\C)/C(=O)OC(C)C(C)(C(=O)O[C@@H]1CCN2C1[C@H](CC2)CO)O -543;91749448;1: Isoipanguline A3;C[C@H]([C@@](C)(C(=O)OC[C@H]1CCN2C1[C@@H](CC2)OC(=O)CC3=CC=CC=C3)OC(=O)C)OC(=O)C -544;91749449;1: Isoipanguline B1;C[C@H]([C@@](C)(C(=O)OC[C@H]1CCN2C1[C@@H](CC2)OC(=O)C3=CC=CC=C3O)O)O -545;91749454;1: 7-(2-Methylbutylryl)platynecine;CCC(C)C(=O)O[C@@H]1CCN2C1[C@H](CC2)CO -546;91749889;1: Ipanguline C5;C/C=C(\C)/C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)C(C)(C(C)OC(=O)/C(=C/C)/C)O -547;91749890;1: Ipanguline C6;C/C=C(\C)/C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)C(C)(C(C)O)O -548;91753677;1: Procerine;CC(C(=O)C)C(=O)O[C@@H]1CCN2[C@@H]1[C@H](C(C2)O)CO -549;91991897;1: {1-[(ethylcarbamoyl)oxy]-2,3-dihydro-1H-pyrrolizin-7-yl}methyl N-ethylcarbamate;CCNC(=O)OCC1=C2C(CCN2C=C1)OC(=O)NCC -550;92019195;1: ethyl 2,7-bis(acetyloxy)-hexahydro-1H-pyrrolizine-1-carboxylate;CCOC(=O)C1C(CN2C1C(CC2)OC(=O)C)OC(=O)C -551;92233018;1: (1R,7R,7aR)-1-({[(2Z)-2-(hydroxymethyl)but-2-enoyl]oxy}methyl)-7-{[(2E)-2-methylbut-2-enoyl]oxy}-octahydropyrrolizin-4-ium-4-olate;C/C=C(\C)/C(=O)O[C@@H]1CC[N+]2([C@@H]1[C@@H](CC2)COC(=O)/C(=C\C)/CO)[O-] -552;92246526;1: (1R,5S,6S,7S,10R,15R,17S)-5,6-dihydroxy-5,6,7-trimethyl-4,8-dioxo-13-(trifluoroacetyl)-3,9,16-trioxa-13-azatetracyclo[8.6.1.0¹,¹?.0¹³,¹?]heptadecan-13-ium;C[C@@H]1C(=O)O[C@@H]2CC[N+]3([C@@H]2[C@@]4(COC(=O)[C@@]([C@@]1(C)O)(C)O)[C@@H](C3)O4)C(=O)C(F)(F)F -553;92263445;1: (1R,7R,7aR)-1-({[(2E)-2-(hydroxymethyl)but-2-enoyl]oxy}methyl)-7-{[(2Z)-2-methylbut-2-enoyl]oxy}-octahydropyrrolizin-4-ium-4-olate;C/C=C(/C)\C(=O)O[C@@H]1CC[N+]2([C@@H]1[C@@H](CC2)COC(=O)/C(=C/C)/CO)[O-] -554;92263446;1: (1R,4E,6S,7R,11R,12S,17S)-4-ethylidene-7,12-dihydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹?,¹?]heptadecane-3,8-dione;C/C=C/1\C[C@@H]([C@@](C(=O)OC[C@@H]2[C@@H](CN3[C@@H]2[C@@H](CC3)OC1=O)O)(C)O)C -555;93504569;1: (1R)-1-ethoxy-7-(ethoxymethyl)-2,3-dihydro-1H-pyrrolizine;CCOCC1=C2[C@@H](CCN2C=C1)OCC -556;98567771;1: (1R,7R,7aR)-1-({[(2Z)-2-(hydroxymethyl)but-2-enoyl]oxy}methyl)-7-{[(2Z)-2-methylbut-2-enoyl]oxy}-octahydropyrrolizin-4-ium-4-olate;C/C=C(/C)\C(=O)O[C@@H]1CC[N+]2([C@@H]1[C@@H](CC2)COC(=O)/C(=C\C)/CO)[O-] -557;100916220;1: 11-O-Acetylbulgarsenine;C[C@@H]1CC(=CC(=O)O[C@@H]2CCN3[C@@H]2[C@H](CC3)COC(=O)[C@]1(C)OC(=O)C)C -558;100976533;1: Iodanthine;C[C@H]1CC(=CC(=O)O[C@@H]2CCN3[C@@H]2[C@H](CC3)COC(=O)[C@@]1(C)O)C -559;101297661;1: Croalbidine;CC(C)[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2[C@H](COC(=O)[C@]([C@]1(C)O)(C)O)[C@H](C3)O -560;101324857;1: Pterophorine;C[C@H]1[C@H]([C@@](C(=O)OCC2=C3[C@@H](CC(=O)N3C=C2)OC(=O)C1=C)(C)OC(=O)C)C -561;101360989;1: Platyphylline N-oxide;C/C=C\1/C[C@H]([C@@](C(=O)OC[C@@H]2CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(C)O)C -562;101526912;1: 7-epi-Deacetylsenaetnin;C/C=C\1/C[C@H]([C@@](C(=O)OCC2=C3[C@@H](CC(=O)N3C=C2)OC1=O)(C)O)C -563;101689715;1: Dehydroseneciphylline;C/C=C/1\CC(=C)[C@@](C(=O)OCC2=C3[C@@H](CCN3C=C2)OC1=O)(C)O -564;101793685;1: Lankongensisine;C[C@H]1CC2([C@@H]([C@]1(C(=O)OCC3CCN4[C@H]3C(CC4)OC2=O)C)C)O -565;101992452;1: Dehydrotrichodesmine;CC(C)[C@@H]1C(=O)O[C@@H]2CCN3C2=C(COC(=O)[C@]([C@@]1(C)O)(C)O)C=C3 -566;102207684;1: [(1S,7R,7aR)-7-[(2-methylbutanoyl)oxy]-hexahydro-1H-pyrrolizin-1-yl]methyl (2S,3R)-2,3-dihydroxy-2-methylbutanoate;CCC(C)C(=O)O[C@@H]1CCN2[C@@H]1[C@H](CC2)COC(=O)[C@](C)([C@@H](C)O)O -567;102207687;1: 4-{[(1R,7S,7aR)-7-(hydroxymethyl)-hexahydro-1H-pyrrolizin-1-yl]oxy}-3-hydroxy-3-methyl-4-oxobutan-2-yl (2E)-2-methylbut-2-enoate;C/C=C(\C)/C(=O)OC(C)C(C)(C(=O)O[C@@H]1CCN2[C@@H]1[C@H](CC2)CO)O -568;102372765;1: (1S,7aalpha)-2beta-Hydroxy-3-oxo-7alpha-(tetrahydro-2H-pyran-2-yloxy)hexahydro-1H-pyrrolizine-1alpha-carboxylic acid ethyl ester;CCOC(=O)[C@H]1[C@@H]2[C@H](CCN2C(=O)[C@@H]1O)OC3CCCCO3 -569;102372767;1: (1S,7aalpha)-2beta-Hydroxy-7alpha-(tetrahydro-2H-pyran-2-yloxy)hexahydro-1H-pyrrolizine-1alpha-carboxylic acid ethyl ester;CCOC(=O)[C@@H]1[C@H](CN2[C@H]1[C@H](CC2)OC3CCCCO3)O -570;102442056;1: Neocroalbidine;CC[C@]1(C(=O)O[C@@H]2CCN3C2[C@H](COC(=O)[C@H]([C@]1(C)O)C)[C@H](C3)O)C -571;102442057;1: Neocroalbidinone;CC[C@]1(C(=O)O[C@@H]2CCN3C2[C@H](COC(=O)[C@H]([C@]1(C)O)C)[C@H](C3=O)O)C -572;102588231;1: Dihydroheliospathuline N-oxide;C[C@@H]([C@@](C(C)C)(C(=O)O[C@@H]1CC[N+]2([C@@H]1C(CC2)CO)[O-])O)O -573;102596225;1: (1S,7aalpha)-1alpha,2beta,6beta-Triacetoxy-7alpha-(acetoxymethyl)hexahydro-1H-pyrrolizine;CC(=O)OC[C@H]1[C@@H](CN2[C@@H]1[C@@H]([C@H](C2)OC(=O)C)OC(=O)C)OC(=O)C -574;102596226;1: (1S,7aalpha)-1alpha,2beta-Bis(tert-butyloxy)-6beta-acetoxy-7alpha-(pivaloyloxymethyl)hexahydro-1H-pyrrolizine;CC(=O)O[C@@H]1CN2C[C@@H]([C@H]([C@@H]2[C@H]1COC(=O)C(C)(C)C)OC(C)(C)C)OC(C)(C)C -575;6440436;1: Petasinine;C/C=C(/C)\C(=O)O[C@H]1CN2CCC[C@H]2[C@H]1CO -576;656392;1: Cremastrine;CC[C@@H](C)[C@H](C(=O)OC[C@H]1CCN2[C@H]1CCC2)O -577;10806120;"1: 3'-Acetyltrachelanthamine ";C[C@H]([C@@](C(C)C)(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)O)OC(=O)C -578;10523;1: Trachelanthamine N-oxide;CC(C)[C@@](C(C)O)(C(=O)OC[C@H]1CC[N+]2([C@H]1CCC2)[O-])O -579;26477;1: Trachelanthamine;CC(C)[C@@](C(C)O)(C(=O)OC[C@H]1CCN2[C@H]1CCC2)O -580;155104;1: Curassavine;CCC(C)C(C(C)O)(C(=O)OCC1CCN2C1CCC2)O -581;155153;"1: Heliovicine -2: Coromandaline -3: Heliocurassavicine -4: Lindelofine -5: Viridiflorine -6: Cynaustraline";C[C@@H]([C@](C(C)C)(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)O)O -582;169554;1: Strigosine;CCC(C)(C(C(=O)OCC1CCN2C1CCC2)O)O -583;4483893;1: (2-hydroxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl)methyl 2-methylbut-2-enoate;CC=C(C)C(=O)OCC1C2CCCN2CC1O -584;5315247;;CCC(C(CC(C)C)(C(=O)OCC1CCN2C1CCC2)O)O -585;10685701;1: Foridinine;C[C@@H]([C@@](C(=O)OC[C@@H]1CCN2[C@H]1CCC2)(C(C)(C)O)O)O -586;13967757;1: 9-Acetyltrachelanthamidine;CC(=O)OC[C@@H]1CCN2[C@H]1CCC2 -587;46930232;;CCC(C)C(=O)OC[C@@H]1CCN2[C@H]1CCC2 -588;51693704;;CC[C@](C)([C@H](C(=O)OC[C@@H]1CC[N+]2([C@@H]1CCC2)[O-])O)O -589;67189194;;CCCC(=O)OCC1CCN2C1CCC2 -590;91747354;1: 9-Angeloyltrachelanthamidine;C/C=C(/C)\C(=O)OC[C@@H]1CCN2[C@H]1CCC2 -591;91747604;1: .beta.-angelyl-trachelanthamine;C/C=C(/C)\C(=O)OC(C)[C@](C(C)C)(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)O[Si](C)(C)C -592;91747607;;C/C=C(\C)/C(=O)OC(C)[C@](C(C)C)(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)O[Si](C)(C)C -593;91749893;1: Minalobine A;CC(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)O -594;91749894;1: Minalobine B;C/C=C(\C)/C(=O)OC[C@@H]1CCN2[C@H]1CCC2 -595;91749895;1: Minalobine C;C[C@@](C=C)(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)O -596;91749896;1: Minalobine D;CCC(C)(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)O -597;91749897;1: Minalobine I;CCC(=O)OC(C)C(C)(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)O -598;91749898;1: Minalobine K;CCC(C)C(=O)OC(C)C(C)(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)O -599;91749899;1: Minalobine M;C/C=C(\C)/C(=O)OC(C)C(C)(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)O -600;101324794;1: Cornucervine;CC(C)C[C@@](CC(=O)OC[C@@H]1CCN2[C@H]1CCC2)(C(=O)OC)O -601;101360427;1: (7aalpha)-1beta-(Acetoxymethyl)hexahydro-1H-pyrrolizine-3-one;CC(=O)OC[C@H]1CC(=O)N2[C@H]1CCC2 -602;118701599;1: [(1S,2R,8R)-2-hydroxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl (Z)-2-methylbut-2-enoate;C/C=C(/C)\C(=O)OC[C@H]1[C@H](CN2C1CCC2)O diff --git a/data/PA_complete_SMILES_fixed.csv b/data/PA_complete_SMILES_fixed.csv deleted file mode 100644 index 47c58a8..0000000 --- a/data/PA_complete_SMILES_fixed.csv +++ /dev/null @@ -1,602 +0,0 @@ -1,O=C1O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]([C@H]1C)(C)O)(C)O -2,C/C=C\1/C[C@@H](C)[C@](O)(CO)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3 -5: Echinatine",O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@]([C@@H](O)C)(C(C)C)O -4,CC([C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O)C -5,O[C@@H]1CC[N+]2([C@@H]1C(=CC2)COC(=O)[C@]([C@@H](O)C)(C(C)C)O)[O-] -6,C/C=C\1/C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3 -2: Inegerrimine",C/C=C/1\C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3 -2: Retrorsine N-oxide",C/C=C\1/C[C@@H](C)[C@](O)(CO)C(=O)OCC2=CC[N+]3([C@H]2[C@H](OC1=O)CC3)[O-] -9,C/C=C\1/CC(=C)[C@](O)(CO)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3 -10,C/C=C/1\C[C@@H](C)[C@](O)(CO)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3 -11,C/C=C\1/C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CC[N+]3([C@H]2[C@H](OC1=O)CC3)[O-] -12,C=C/C/1=C/[C@H](C)[C@](C)(OC(=O)C)C(=O)OCC2=CC[N+]3(C2([C@H](OC1=O)CC3)[O-])C -2: 7-Angelyleuropine",COC(C(C(O)(C)C)(C(=O)OCC1=CCN2C1C(CC2)OC(=O)C(=CC)C)O)C -14,C/C=C\1/CC(=C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3 -15,CO[C@@H]([C@](C(=O)OCC1=CC[N+]2([C@H]1[C@@H](O)CC2)[O-])(C(C)C)O)C -16,COC(C(C(=O)OCC1=CCN2C1C(O)CC2)(C(C)C)O)C -2: Heliotridine",OCC1=CCN2[C@H]1[C@H](O)CC2 -18,O=C1OCC2=CCN3C2C(CC3)OC(=O)C2(CC(C1(C)O)C)OC2C -19,CC([C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@@]([C@@H]1O)(O)[C@H](O)C)C -20,CC[C@@]1(O)C[C@@H](C)[C@](C)(OC(=O)C)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3 -2: Crispatine",O=C1O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@H]([C@]([C@H]1C)(C)O)C -4: Echiumine",C/C=C(\C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@@H](O)C)(C(C)C)O)/C -4: 7-Tiglyl-9-viridiflorylretronecine",C/C=C(/C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@@H](O)C)(C(C)C)O)\C -2: Cynoglossum",C/C=C(/C(=O)OC1CCN2C1C(=CC2)COC(=O)C1(O)C(C)OC(=O)C1C)\C -25,C/C=C\1/CC(=C)[C@](O)(CO)C(=O)OCC2=CC[N+]3([C@H]2[C@H](OC1=O)CC3)[O-] -2: 19-Hydroxysenecionine",C/C=C/1\CC(CO)C(C)(O)C(=O)OCC2=CCN3C2C(OC1=O)CC3 -27,OC/C=C/1\C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CC[N+]3([C@]2([C@H](OC1=O)CC3)O)C -28,C/C=C\1/CC2(CO)OC2(C)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3 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-580,CCC(C(C(=O)OCC1CCN2C1CCC2)(C(O)C)O)C -6: Cynaustraline",CC([C@](C(=O)OC[C@@H]1CCN2[C@H]1CCC2)([C@@H](O)C)O)C -582,CCC(C(C(=O)OCC1CCN2C1CCC2)O)(O)C -583,CC=C(C(=O)OCC1C(O)CN2C1CCC2)C -584,CCC(C(C(=O)OCC1CCN2C1CCC2)(CC(C)C)O)O -585,C[C@@H]([C@](C(O)(C)C)(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)O)O -586,CC(=O)OC[C@@H]1CCN2[C@H]1CCC2 -587,CCC(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)C -588,CC[C@]([C@H](C(=O)OC[C@@H]1CC[N+]2([C@@H]1CCC2)[O-])O)(O)C -589,CCCC(=O)OCC1CCN2C1CCC2 -590,C/C=C(\C(=O)OC[C@@H]1CCN2[C@H]1CCC2)/C -591,C/C=C(\C(=O)OC([C@@](C(=O)OC[C@@H]1CCN2[C@H]1CCC2)(C(C)C)O[Si](C)(C)C)C)/C -592,C/C=C(/C(=O)OC([C@@](C(=O)OC[C@@H]1CCN2[C@H]1CCC2)(C(C)C)O[Si](C)(C)C)C)\C -593,O=C(C(O)C)OC[C@@H]1CCN2[C@H]1CCC2 -594,C/C=C(/C(=O)OC[C@@H]1CCN2[C@H]1CCC2)\C -595,C=C[C@](C(=O)OC[C@@H]1CCN2[C@H]1CCC2)(O)C -596,CCC(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)(O)C -597,CCC(=O)OC(C(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)(O)C)C -598,CCC(C(=O)OC(C(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)(O)C)C)C -599,C/C=C(/C(=O)OC(C(C(=O)OC[C@@H]1CCN2[C@H]1CCC2)(O)C)C)\C -600,COC(=O)[C@](CC(=O)OC[C@@H]1CCN2[C@H]1CCC2)(CC(C)C)O -601,CC(=O)OC[C@H]1CC(=O)N2[C@H]1CCC2 -602,C/C=C(\C(=O)OC[C@H]1[C@@H](O)CN2C1CCC2)/C diff --git a/data/efsa.csv b/data/efsa.csv index efcc132..eda38a7 100644 --- a/data/efsa.csv +++ b/data/efsa.csv @@ -1,3 +1,4 @@ +ID,SMILES,Mutagenicity efsa_1214-39-7,c1ccc(cc1)CNc1ncnc2c1[nH]cn2,0 efsa_148-24-3,OS(=O)(=O)O.Oc1cccc2c1nccc2.Oc1cccc2c1nccc2,1 efsa_148-24-3,Oc1cccc2c1nccc2,1 diff --git a/data/hansen.csv b/data/hansen.csv index e6c855d..f69ea50 100644 --- a/data/hansen.csv +++ b/data/hansen.csv @@ -1,3 +1,4 @@ +ID,SMILES,Mutagenicity hansen_2475-33-4,O=C1c2ccccc2C(=O)c2c1c1[nH]c3c(c1c1c2[nH]c2c1ccc1c2C(=O)c2ccccc2C1=O)ccc1c3C(=O)c2ccccc2C1=O,0 hansen_820-75-7,NNC(=O)CNC(=O)/C=N#N,1 hansen_2435-76-9,N1C(=O)/C(=N#N)/C=NC1=O,1 diff --git a/data/mutagenicity-merged.id b/data/mutagenicity-merged.id index 3125d63..abe9002 100644 --- a/data/mutagenicity-merged.id +++ b/data/mutagenicity-merged.id @@ -1 +1 @@ -5b9120b0ca626908c7c17734 +5bba44beca62690a261f82b5 diff --git a/scripts/carcinogenicity2csv.rb b/scripts/carcinogenicity2csv.rb deleted file mode 100755 index bed0907..0000000 --- a/scripts/carcinogenicity2csv.rb +++ /dev/null @@ -1,25 +0,0 @@ -#!/usr/bin/env ruby -#require_relative '../../lazar/lib/lazar.rb' - -i = 0 -activities = [] -File.readlines(ARGV[0]).each do |line| - if i > 2 - tokens = line.split "," - p line if tokens[1].empty? - activities << [tokens[1],tokens[3]] - end - i += 1 -end - -puts "SMILES,Activity" -activities.each_slice(100) do |slice| # get SMILES in chunks - sids = slice.collect{|e| e[0]} - smiles = `curl https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/cid/#{sids.join(",")}/property/CanonicalSMILES/TXT`.split("\n") - abort("Could not get SMILES for all SIDs from PubChem") unless sids.size == smiles.size - smiles.each_with_index do |smi,i| - act = slice[i] - puts [smi.chomp,act[1]].join(",") - end -end - diff --git a/scripts/convert_pa.rb b/scripts/convert_pa.rb deleted file mode 100755 index 779aded..0000000 --- a/scripts/convert_pa.rb +++ /dev/null @@ -1,12 +0,0 @@ -#!/usr/bin/env ruby -require_relative '../../lazar/lib/lazar.rb' - -while STDIN.gets - tokens = $_.chomp.encode("UTF-8", {:invalid => :replace, :undef => :replace}).split(";") - begin - c = OpenTox::Compound.from_smiles tokens.last - puts "#{tokens[0]},#{c.smiles}" - rescue #=> e - STDERR.puts $_ - end -end diff --git a/scripts/efsa2csv.rb b/scripts/efsa2csv.rb deleted file mode 100755 index 48d4fb8..0000000 --- a/scripts/efsa2csv.rb +++ /dev/null @@ -1,28 +0,0 @@ -#!/usr/bin/env ruby -require 'csv' -require_relative '../../lazar/lib/lazar.rb' - -i = 0 -db = {} -CSV.foreach(ARGV[0], :encoding => "UTF-8", :col_sep => "\t", :liberal_parsing => true) do |row| - #STDERR.puts i if i%100 == 0 - if i > 0 and row[11] and !row[11].empty? and row[24].match(/Salmonella/i) and ( row[25].match("TA 98") or row[25].match("TA 100") ) and row[33] - begin - c = OpenTox::Compound.from_smiles(row[11].gsub('"','')).smiles - rescue - c = OpenTox::Compound.from_inchi(row[12]).smiles # some smiles (row[11]) contain non-parseable characters - end - db[c] ||= {} - db[c][:id] ||= "efsa_#{row[2]}" - if row[33].match(/Positiv/i) - db[c][:value] = 1 # at least one positive result in TA 98 or TA 100 - elsif row[33].match(/Negativ/i) - db[c][:value] ||= 0 - end - end - i += 1 -end - -db.each do |s,v| - puts [v[:id],s,v[:value]].join "," -end diff --git a/scripts/import-csv.rb b/scripts/import-csv.rb deleted file mode 100755 index 255e342..0000000 --- a/scripts/import-csv.rb +++ /dev/null @@ -1,8 +0,0 @@ -#!/usr/bin/env ruby -require_relative '../../lazar/lib/lazar' -include OpenTox - -dataset = Dataset.from_csv_file ARGV[0] -puts dataset.id.to_s - - -- cgit v1.2.3