From ac01d39d33ba4413e2e2341c098063737cbf11b5 Mon Sep 17 00:00:00 2001 From: gebele Date: Tue, 14 Mar 2017 10:06:25 +0100 Subject: renamed activities --- .../DSSTox_Carcinogenic_Potency_DBS_Mouse.csv | 1954 ++--- ...STox_Carcinogenic_Potency_DBS_MultiCellCall.csv | 2238 +++--- .../DSSTox_Carcinogenic_Potency_DBS_Rat.csv | 2394 +++--- classification/blood-brain-barrier.csv | 278 +- classification/kazius.csv | 8138 ++++++++++---------- 5 files changed, 7501 insertions(+), 7501 deletions(-) (limited to 'classification') diff --git a/classification/DSSTox_Carcinogenic_Potency_DBS_Mouse.csv b/classification/DSSTox_Carcinogenic_Potency_DBS_Mouse.csv index d1583c2..e62f951 100644 --- a/classification/DSSTox_Carcinogenic_Potency_DBS_Mouse.csv +++ b/classification/DSSTox_Carcinogenic_Potency_DBS_Mouse.csv @@ -1,978 +1,978 @@ STRUCTURE_SMILES,ActivityOutcome_CPDBAS_Mouse -ClC1=C(C(=C(C(=C1OC)Cl)Cl)Cl)Cl,active -ClC(Cl)Cl,active -ClC(Cl)Br,active -ClC#CCl,active -ClC(C(Cl)Cl)(Cl)Cl,active 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+O=C(C(SP(=O)(OC)OC)CC(=O)OCC)OCC,non-carcinogenic +C1(C2=CC=CC=C2)=CC(=C(C=C1)NC(=O)C)O,non-carcinogenic +CC1=C(Cl)C(=O)OC2=C1C=CC(=C2)OP(=S)(OCC)OCC,non-carcinogenic +C1(CCCCC1[N+]).O=S(=O)([O-])O,non-carcinogenic +ClC1=C(C=C(C=C1C(=O)O)Cl)N,non-carcinogenic +C1(CCCCC1)N.[H]Cl,non-carcinogenic +NNC1=NC(=CS1)C2=CC=CC=C2,non-carcinogenic +C1(C[C@H]([C@@H]([C@H]1CCCCCCC(=O)OC)/C=C/CC(O)(CCCC)C)O)=O,non-carcinogenic +O=C(CN=C2C3=CC=CC=C3)NC1=C2N(N=C1C)CC,non-carcinogenic +O[As](=O)(C1=CC=C(C=C1)NC(=O)N)O,non-carcinogenic +C1(C=CC=CN=1)CCl.Cl,non-carcinogenic +O=C(CN1C(=O)CCC1)NC2=C(C=CC=C2C)C,non-carcinogenic +O[As](=O)(C1=CC(=C(C=C1)O)[N+](=O)[O-])O,non-carcinogenic +C1(C2=CC=C(C(=C2)Cl)N=NC(C(C)=O)C(=O)NC3=C(C=C(C(=C3)OC)Cl)OC)=CC(=C(C=C1)N=NC(C(C)=O)C(=O)NC4=CC(=C(C=C4OC)Cl)OC)Cl,non-carcinogenic +ClC1=C(C=C(C(=C1)Cl)Cl)OCC(=O)O,non-carcinogenic +O(S(=O)(=O)C)CCCCOS(=O)(C)=O,non-carcinogenic +N1C(=O)C(CC)(CCC(C)C)C(=O)NC1=O,non-carcinogenic +CC(CO)O,non-carcinogenic +NC1=NC(=NC(=N1)N)C2=CC=CC=C2,non-carcinogenic +CC(=O)N[C@@H](CS)C(=O)O,non-carcinogenic +OC(OC(O)CC)CC,non-carcinogenic +C1(NS(=O)(=O)[O-])CCCCC1.[Na+],non-carcinogenic +NC1=CC=CC=C1,non-carcinogenic +O=C(C)OC/C=C(C)/CC/C=C(C)/C,non-carcinogenic +CC(C)NCC(O)COc1ccc(cc1)NC(C)=O,non-carcinogenic +C1(OCC=C)=CC=C(CC(=O)O)C=C1Cl,non-carcinogenic +CCN(CC)C(=O)C1=CC=CC(C)=C1,non-carcinogenic +C1(CCNC(NC(N)=N)=N)=CC=CC=C1.[H]Cl,non-carcinogenic +C1CCNCC1,non-carcinogenic +NCCS(O)(=O)=O,non-carcinogenic +C1(CCN=C=S)=CC=CC=C1,non-carcinogenic +C1(CSCCNC(NC)=NC#N)=C(C)NC=N1,non-carcinogenic +O=[Cr]O[Cr]=O,non-carcinogenic +c1(n(cnc1)C)C[C@@H]2[C@@H](C(=O)OC2)CC,non-carcinogenic +Nc1cc(Cl)c(N)cc1.OS(O)(=O)=O,non-carcinogenic +Cl\C2=C(/Cl)C3(Cl)C1C4CC(C1C2(Cl)C3(Cl)Cl)C5OC45,non-carcinogenic +S=C(S[Pb]SC(N(C)C)=S)N(C)C,non-carcinogenic +O=[N+](C1=C(C(=CC(=C1)C(F)(F)F)[N+](=O)[O-])N(CCC)CCC)[O-],non-carcinogenic +N=C\2/N=C3/O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N3/C=C/2,non-carcinogenic +O=[N+](C1=CC(=C(C=C1)C(=O)O)N)[O-],non-carcinogenic +O=[N+](C1=C2C(=CC=C1)C=CC=C2)[O-],non-carcinogenic +ClC1/C=C\C2C1C3(Cl)C(/Cl)=C(/Cl)C2(Cl)C3(Cl)Cl,non-carcinogenic +C1(C(=CC=C(C=1)C)N)C.[H]Cl,non-carcinogenic +ClC1=C(C(=C(C(=C1Cl)Cl)Cl)Cl)[N+](=O)[O-],non-carcinogenic +O=NN1CN(C2)CN(N=O)CN2C1,non-carcinogenic +CC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-],non-carcinogenic +C1(=CC=C(N)C=C1)C.[H]Cl,non-carcinogenic +NC(=S)C(=S)N,non-carcinogenic +O=[N+](C1=CC=C(C=C1)N)[O-],non-carcinogenic +O=C(C1=C(C=CC=C1)C(=O)OCC=C)OCC=C,non-carcinogenic +ClC1(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl,non-carcinogenic +O=[N+](C1=CC=C(C=C1)Cl)[O-],non-carcinogenic +O=S(C1=CC=C2C(C=CC(O)=C2\N=N/C3=CC=C(S(=O)([O-])=O)C=C3)=C1)([O-])=O.[Na+].[Na+],non-carcinogenic +O=[N+](C1=CC(=C(C=C1)N)N)[O-],non-carcinogenic +NC1=C(C=C(C=C1)N)[N+](=O)[O-],non-carcinogenic +ClCC(=O)C1=CC=C(NC(=O)C)C=C1,non-carcinogenic +ClC(=C(C1=CC=C(C=C1)OC)C2=CC=C(C=C2)OC)C3=CC=C(C=C3)OC,non-carcinogenic +[Na+].O=C([O-])[C@@H](N)CCC(O)=O,non-carcinogenic +O=S1(=O)CC=CC1,non-carcinogenic +O[C@H]([C@H](O)CNCCCl)[C@H](O)[C@H](O)CNCCCl,non-carcinogenic +[Ti+2](C1=CC=CC1)C2(=CC=CC2).[Cl-].[Cl-],non-carcinogenic +O[C@@H](CO)[C@@H](O1)C(OCC)=C(O)C1=O,non-carcinogenic +OC(=O)[C@@H](N)CSCC,non-carcinogenic +CC(OC(=O)OC1CCCCC1)OC(=O)c5cccc6nc(OCC)n(Cc2ccc(cc2)c3ccccc3C\4=N\N=N/N/4)c56,non-carcinogenic +O[C@@H]1C2[C@@]34C5=C(C=CC(=C5O2)OC)CC(C3C=C1)N(C)CC4,non-carcinogenic +NC1=NC(N)=NC(C2=CC(Cl)=CC=C2Cl)=N1.O=C(O)/C=C\C(O)=O,non-carcinogenic +C/C=C/C1=CC=C(C=C1)OC,non-carcinogenic +O=[C@]([C@@H]1C[C@@H](O)CN1N=O)O,non-carcinogenic +C(C(F)(Cl)Cl)(F)(F)Cl,non-carcinogenic +C1(C(COCCOC(=O)CCCCCCCC=CCCCCCCCC)OCCO)OC(OCCO)CC1OCCO,non-carcinogenic +O=[Bi]Cl,non-carcinogenic +O=C(O[C@H](CC)[C@](O)(C)[C@H](O)[C@@H](C)C2=O)[C@H](C)[C@@H](O[C@H]3C[C@](OC)(C)[C@@H](O)[C@H](C)O3)[C@H](C)[C@H]([C@@](O)(C)C[C@H]2C)O[C@H]1[C@H](O)[C@@H]([N@H+](C)C)C[C@@H](C)O1.[O-]C(CCCCCCCCCCCCCCCCC)=O,non-carcinogenic +O[Sn](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3,non-carcinogenic +O=[As](O)(O)[O-].[Na+],non-carcinogenic +CC(C=NOC(=O)NC)(SC)C,non-carcinogenic diff --git a/classification/blood-brain-barrier.csv b/classification/blood-brain-barrier.csv index a8c0587..31f39bd 100644 --- a/classification/blood-brain-barrier.csv +++ b/classification/blood-brain-barrier.csv @@ -1,6 +1,6 @@ SMILES,"Blood-Brain-Barrier Penetration" -c12c(c(ccc1)Cl)C(N(Cc1n2cnc1c1nc(on1)[C@](CO)(C)O)C)=O,nonpenetrating -NCCc1cn2c(n1)cccc2,nonpenetrating +c12c(c(ccc1)Cl)C(N(Cc1n2cnc1c1nc(on1)[C@](CO)(C)O)C)=O,non-penetrating +NCCc1cn2c(n1)cccc2,non-penetrating CCCN(CCC)CCc1ccc(c2c1CC(N2)=C)O,penetrating c1(c2c(cc(F)cc2)on1)C1CCN(CCc2c(n3c([C@@H](CCC3)O)nc2C)=O)CC1,penetrating c12c(C(c3ccccc3)=NCc3n1c(nn3)C)cc(Cl)cc2,penetrating @@ -11,21 +11,21 @@ c1(c(cccc1)OC(C)=O)C(O)=O,penetrating N(C(NCCCl)=O)(CCCl)N=O,penetrating c12c(n(c(=O)n(c1=O)C)C)ncn2C,penetrating N1(c2c(cccc2)C=Cc2c1cccc2)C(N)=O,penetrating -c1(N(CCCl)CCCl)ccc(CCCC(O)=O)cc1,nonpenetrating +c1(N(CCCl)CCCl)ccc(CCCC(O)=O)cc1,non-penetrating N1(c2c(Sc3c1cccc3)ccc(c2)Cl)CCCN(C)C,penetrating -c1(c([nH]cn1)C)CSCCN\C(=[NH]\C#N)NC,nonpenetrating +c1(c([nH]cn1)C)CSCCN\C(=[NH]\C#N)NC,non-penetrating c1(NC=2NCCN2)c(cccc1Cl)Cl,penetrating c12[C@]34[C@@H]5[C@H]([N@@](C)CC4)Cc2ccc(c1O[C@H]3[C@@H](O)C=C5)OC,penetrating N1(c2c(CCc3c1cccc3)cccc2)CCCNC,penetrating -n1(c2c(c(ncn2)O)nc1)[C@@H]1O[C@H](CO)CC1,nonpenetrating +n1(c2c(c(ncn2)O)nc1)[C@@H]1O[C@H](CO)CC1,non-penetrating n1(c2c(cc(Cl)cc2)[nH]c1=O)C1CCN(CCCn2c3c(cccc3)[nH]c2=O)CC1,penetrating N1([C@@H](c2ccc(Cl)cc2)c2ccccc2)CCN(CCOCCO)CC1,penetrating c1([C@@H](C(O)=O)C)ccc(CC(C)C)cc1,penetrating -c1c(c(ncc1)CCCCNc1nc(c(c[nH]1)Cc1ccc(nc1)C)=O)OC,nonpenetrating +c1c(c(ncc1)CCCCNc1nc(c(c[nH]1)Cc1ccc(nc1)C)=O)OC,non-penetrating N1(c2c(CCc3c1cccc3)cccc2)CCCN(C)C,penetrating -c12c(c(CC(O)=O)c(n1C(c1ccc(Cl)cc1)=O)C)cc(OC)cc2,nonpenetrating +c12c(c(CC(O)=O)c(n1C(c1ccc(Cl)cc1)=O)C)cc(OC)cc2,non-penetrating c12c(C(N(Cc3n1cnc3c1noc(n1)C(C)C)C)=O)c(ccc2)Cl,penetrating -CN(C)Cc1ccc(CSCCNc2nc(=O)c(Cc3ccc(C)nc3)c[nH]2)o1,nonpenetrating +CN(C)Cc1ccc(CSCCNc2nc(=O)c(Cc3ccc(C)nc3)c[nH]2)o1,non-penetrating N(c1ccccn1)(Cc1ccc(OC)cc1)CCN(C)C,penetrating N12[C@H](c3c(cccc3)Cc3c1cccc3)C[N@](C)CC2,penetrating c12c(C(c3c(cccc3)F)=NCc3n1c(nc3)C)cc(Cl)cc2,penetrating @@ -38,14 +38,14 @@ c1ccc(c(c1)[C@H](CC=C)N)c1c2c(on1)cccc2,penetrating c1c2c(ccc1)[C@@]1([C@@H](c3cccc(c3O2)C)C[N@](CC1)C)O,penetrating c1c2c(cc(c1)Cl)[C@@H]1[C@H](c3ccccc3O2)CN(C1)C,penetrating c12C(c3ccccc3)=N[C@H](O)C(Nc1ccc(c2)Cl)=O,penetrating -c1(oc([CH2+]SCCN\C(=C\[N+](=O)[O-])NC)cc1)CN(C)C,nonpenetrating +c1(oc([CH2+]SCCN\C(=C\[N+](=O)[O-])NC)cc1)CN(C)C,non-penetrating c1(c2c(cc(F)cc2)on1)C1CCN(CCc2c(n3c(CCCC3)nc2C)=O)CC1,penetrating C1(C(NC(=[O-])NC1=O)=O)([C@H](CCC)C)[CH-]C,penetrating c12[C@]3([C@H]([N@](C)CC3)N(c1ccc(c2)OC(Nc1ccccc1)=O)C)C,penetrating c12[C@]3([C@@H](N(C)c1ccc(c2)OC(NC)=O)[N@](C)CC3)C,penetrating N1(c2c(Sc3c1cccc3)cccc2)CCCN(C)C,penetrating -c1(c(cccc1)O)C(O)=O,nonpenetrating -c1c(c(ncc1Br)CCCCNc1nc(c(c[nH]1)Cc1ccc(nc1)C)=O)C,nonpenetrating +c1(c(cccc1)O)C(O)=O,non-penetrating +c1c(c(ncc1Br)CCCCNc1nc(c(c[nH]1)Cc1ccc(nc1)C)=O)C,non-penetrating c12c(n(c(=O)n(c1=O)C)C)nc[nH]2,penetrating N1(c2c(Sc3c1cccc3)ccc(c2)SC)CC[C@H]1[N@@](CCCC1)C,penetrating C1[C@H]2[C@H]3[C@@H](C4=C(CC(=O)CC4)C[C@H]3C)CC[C@@]2([C@@](C#C)(O)C1)C,penetrating @@ -65,7 +65,7 @@ c12c(C(c3c(cccc3)F)=N[C@@H](c3n1c(nc3)C)O)cc(Cl)cc2,penetrating c1c(NC(C)=O)ccc(O)c1,penetrating n1(c2ccccc2)c(c(N(C)C)c(n1C)C)=O,penetrating C1(C(NC(=O)NC1=O)=O)(CCC(C)C)CC,penetrating -c1(ccc(CC(N)=O)cc1)OC[C@@H](CNC(C)C)O,nonpenetrating +c1(ccc(CC(N)=O)cc1)OC[C@@H](CNC(C)C)O,non-penetrating c1ccccc1,penetrating c12n(c3c(c(ccc3)Br)C(N3[C@H]1CCC3)=O)cnc2C(OC(C)(C)C)=O,penetrating c1(C2(CCN(CCCC(c3ccc(F)cc3)=O)CC2)O)ccc(Br)cc1,penetrating @@ -125,8 +125,8 @@ C(Cl)(Cl)Cl,penetrating c1c(nccc1)CCNC,penetrating c1c(nccc1)CCN(C)C,penetrating n1c(scc1)CCN,penetrating -n1c(scc1c1ccccc1)CCN,nonpenetrating -c1c(nc2n1cccc2)CCN,nonpenetrating +n1c(scc1c1ccccc1)CCN,non-penetrating +c1c(nc2n1cccc2)CCN,non-penetrating n1([C@H]2C[C@H](N=[N+]=N)[C@H](O2)CO)c([nH]c(=O)c([cH+]1)C)=O,penetrating c1c(cccc1C)C,penetrating c1(c(cccc1)C)C,penetrating @@ -136,12 +136,12 @@ c12[C@@H]3[C@@H](c4c(cccc4)N(c1cccc2)C(N)=O)O3,penetrating c12c(nc(c(c1C(N[C@@H](CC)c1ccccc1)=O)C)c1ccccc1)cccc2,penetrating c1cc(ccc1CCCC(OC(C)(C)C)=O)N(CCCl)CCCl,penetrating C(=C)(Cl)(Cl)Cl,penetrating -c1(ncccc1NC(C)C)N1CCN(C(c2cc3cc(NS(C)(=O)=O)ccc3[nH]2)=O)CC1,nonpenetrating -C(c1ccccc1)(c1ccccc1)OC1CCN(CCCC(c2ccc(C(C)(C)C)cc2)=O)CC1,nonpenetrating +c1(ncccc1NC(C)C)N1CCN(C(c2cc3cc(NS(C)(=O)=O)ccc3[nH]2)=O)CC1,non-penetrating +C(c1ccccc1)(c1ccccc1)OC1CCN(CCCC(c2ccc(C(C)(C)C)cc2)=O)CC1,non-penetrating N1(c2c(NC(c3c1cccc3)=O)cccn2)C(CN1CCN(C)CC1)=O,penetrating c12c(Sc3c(N1C[C@@H](N(C)C)C)cccc3)cccc2,penetrating s1cc(CSCCN\C(NC)=[NH]\C#N)nc1\[NH]=C(\N)N,penetrating -c1cc(c2nc(sc2)CCN)ccc1,nonpenetrating +c1cc(c2nc(sc2)CCN)ccc1,non-penetrating c1cc(CCNC)ncc1,penetrating c1cc(CCN(C)C)ncc1,penetrating s1c(ncc1)CCN,penetrating @@ -149,13 +149,13 @@ c1nc(C2CCN(CC2)C(NC2CCCCC2)=S)c[nH]1,penetrating c1ccc2Oc3c(cc(cc3)Cl)[C@@H]3[C@@H](c2c1)C[N@](CC3)C,penetrating c1c(Cl)nc(N2CCN(CCCCN3C(CCC3)=O)CC2)cc1C(F)(F)F,penetrating c1ccc2Oc3c(cc(cc3)Cl)[C@@H]3[C@@H](c2c1)CNCC3,penetrating -c1c(c(ncc1)CSCCN\C(=[NH]\C#N)NCC)Br,nonpenetrating +c1c(c(ncc1)CSCCN\C(=[NH]\C#N)NCC)Br,non-penetrating c1cc(ncc1)CSCCNc1c(cc[nH]1)[N+](=O)[O-],penetrating c1(cc(nc(c1C)C)C(SC(CNc1c(cc[nH]1)[N+](=O)[O-])(C)C)(C)C)C,penetrating n1c(csc1\[NH]=C(\N)N)c1ccccc1,penetrating -n1c(csc1\[NH]=C(\N)N)c1cccc(c1)N,nonpenetrating -n1c(csc1\[NH]=C(\N)N)c1cccc(c1)NC(C)=O,nonpenetrating -n1c(csc1\[NH]=C(\N)N)c1cccc(c1)N\C(NC)=[NH]\C#N,nonpenetrating +n1c(csc1\[NH]=C(\N)N)c1cccc(c1)N,non-penetrating +n1c(csc1\[NH]=C(\N)N)c1cccc(c1)NC(C)=O,non-penetrating +n1c(csc1\[NH]=C(\N)N)c1cccc(c1)N\C(NC)=[NH]\C#N,non-penetrating s1cc(nc1\[NH]=C(\N)N)C,penetrating c1(c(oc(c1C)C(N(C(C)(N)C)C(N)(C)C)(C)C)C)C.C[NH+]O.[OH-],penetrating [NH]C(CC(C)C([N@@](C(C)(C)C)C(N)(C)N)(C)C)c1c(c(c[nH+][o+]1)C)[O-],penetrating @@ -165,9 +165,9 @@ C1CN(CCC1)Cc1cccc(c1)OCCCO,penetrating C1CN(CCC1)Cc1cccc(c1)OCCCNc1ncccc1,penetrating C1CN(CCC1)Cc1cccc(c1)OCCCNc1nccs1,penetrating C1CN(CCC1)Cc1cccc(c1)OCCCNc1nc2c(o1)cccc2,penetrating -c1c(oc(c1)CN(C)C)CSCCNc1nc(c(c[nH]1)Cc1cc2c(cc1)cccc2)=O,nonpenetrating -CN(C)Cc1oc(cc1)CSCCNC=1NC=C(CN1)Cc1cnc(cc1)C,nonpenetrating -c1(nccc(c1)c1nc([nH]n1)N)N(C)C,nonpenetrating +c1c(oc(c1)CN(C)C)CSCCNc1nc(c(c[nH]1)Cc1cc2c(cc1)cccc2)=O,non-penetrating +CN(C)Cc1oc(cc1)CSCCNC=1NC=C(CN1)Cc1cnc(cc1)C,non-penetrating +c1(nccc(c1)c1nc([nH]n1)N)N(C)C,non-penetrating n1(c(c2nc[nH]c2n(c1=O)C)=O)C,penetrating c1c2CCOc2c(cc1OC)CN[C@@H]1CCCN[C@H]1c1ccccc1,penetrating c1(cc(N\C(=[NH]\c2cccc(c2)CC)C)ccc1)CC,penetrating @@ -178,115 +178,115 @@ c12c(ncn1COCCO)c([nH]c(n2)N)=O,penetrating c12c(nc([nH]1)NC(OC)=O)cc(SCCC)cc2,penetrating C12(CC3CC(C1)CC(C2)C3)N,penetrating c1(ccccc1)C[C@H](C)N,penetrating -S(CCNCCCN)P(O)(O)=O,nonpenetrating +S(CCNCCCN)P(O)(O)=O,non-penetrating O([C@H]1[C@@H](C[C@H](N)[C@H]([C@@H]1O)O[C@H]1O[C@@H]([C@@H](O)[C@@H]([C@H]1O)O)CN)NC([C@H](CCN)O)=O)[C@H]1O[C@@H]([C@@H](O)[C@@H]([C@H]1O)N)CO,penetrating -c1(c(cc(N)cc1)O)C(O)=O,nonpenetrating +c1(c(cc(N)cc1)O)C(O)=O,non-penetrating n1([C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)c(nc(N)cc1)=O,penetrating c1(c(nc[nH]1)C(N)=O)\N=N\N(C)C,penetrating -c12c([C@H](C[C@@](C2)(C(C)=O)O)O[C@H]2C[C@@H]([C@H](O)[C@@H](O2)C)N)c(c2C(c3c(cccc3C(c2c1O)=O)OC)=O)O,nonpenetrating -C1[C@@H]2[C@](C(=C3C(c4c(ccc(c4[C@H]([C@@H]13)O)Cl)O)=O)O)(C(C(C(N)=O)=C([C@H]2N(C)C)O)=O)O,nonpenetrating +c12c([C@H](C[C@@](C2)(C(C)=O)O)O[C@H]2C[C@@H]([C@H](O)[C@@H](O2)C)N)c(c2C(c3c(cccc3C(c2c1O)=O)OC)=O)O,non-penetrating +C1[C@@H]2[C@](C(=C3C(c4c(ccc(c4[C@H]([C@@H]13)O)Cl)O)=O)O)(C(C(C(N)=O)=C([C@H]2N(C)C)O)=O)O,non-penetrating Clc1ccc2NC(=O)CC(=O)N(c3ccccc3)c2c1,penetrating C=1(c2c(NC(CN1)=O)ccc(c2)Cl)c1ccccc1,penetrating N1(c2c(Sc3c1cccc3)cccc2)CCCNC,penetrating -N1(C[C@@H](N2CC(NC(C2)=O)=O)C)CC(NC(C1)=O)=O,nonpenetrating +N1(C[C@@H](N2CC(NC(C2)=O)=O)C)CC(NC(C1)=O)=O,non-penetrating c12[C@@]34[C@@H]([C@H]([N@@](C)CC3)Cc1ccc(c2)OC)CCCC4,penetrating -N12[C@]([C@@H]3CCCN3C([C@@H]1Cc1ccccc1)=O)(OC(NC([C@@H]1C[C@@H]3c4c5c(c[nH]c5ccc4)C[C@H]3[N@@](C1)C)=O)(C)C2=O)O,nonpenetrating +N12[C@]([C@@H]3CCCN3C([C@@H]1Cc1ccccc1)=O)(OC(NC([C@@H]1C[C@@H]3c4c5c(c[nH]c5ccc4)C[C@H]3[N@@](C1)C)=O)(C)C2=O)O,non-penetrating N(C(SSC(N(CC)CC)=S)=S)(CC)CC,penetrating -c12c([C@H](C[C@@](C2)(C(CO)=O)O)O[C@H]2C[C@@H]([C@H](O)[C@@H](O2)C)N)c(c2C(c3c(cccc3C(c2c1O)=O)OC)=O)O,nonpenetrating 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-c12[C@H]([C@@H]3[C@H](COC3=O)[C@@H](c1cc1OCOc1c2)O[C@@H]1O[C@H]2[C@@H](O[C@H](C)OC2)[C@@H]([C@H]1O)O)c1cc(c(O)c(c1)OC)OC,nonpenetrating +c12[C@H]([C@@H]3[C@H](COC3=O)[C@@H](c1cc1OCOc1c2)O[C@@H]1O[C@H]2[C@@H](O[C@H](C)OC2)[C@@H]([C@H]1O)O)c1cc(c(O)c(c1)OC)OC,non-penetrating c1(nc(CSCC\C(=[NH]\S(N)(=O)=O)N)cs1)\[NH]=C(\N)N,penetrating c1(C(Cn2cncn2)(Cn2cncn2)O)c(cc(F)cc1)F,penetrating P(C(=O)O)(=O)(O)O,penetrating C1(CC(O)=O)(CCCCC1)CN,penetrating -N12[C@@H]([C@@H](NC(c3c4c(ccc3OCC)cccc4)=O)[C-]2=O)SC([C@@H]1C(=O)O)(C)C,nonpenetrating -c12c(c(c(C(O)=O)cn1CC)=O)ccc(n2)C,nonpenetrating -C1[C@@H]2CCCC[C@@H]2C[N@](C[C@H]([C@@H](NC(c2c(c(ccc2)O)C)=O)CSc2ccccc2)O)[C@@H]1C(NC(C)(C)C)=O,nonpenetrating -N1(c2c(Sc3c1cccc3)ccc(c2)SC)CC[C@H]1NCCCC1,nonpenetrating -c12c([nH]c(n1)[S@@](Cc1c(c(c(C)cn1)OC)C)=O)ccc(c2)OC,nonpenetrating -N12[C@@H]([C@@H](NC(c3c(c4ccccc4)noc3C)=O)[C-]2=O)SC([C@@H]1C(=O)O)(C)C,nonpenetrating 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c12c([nH]cc2)cccc1OC[C@@H](CNC(C)C)O,penetrating c12c(C[C@@H]([C@@H](C([C@H]([C@@H](C)O)O)=O)OC)[C@@H](C1=O)OC1C[C@@H](O[C@H]3C[C@@H](O[C@H]4C[C@]([C@H](O)[C@H](O4)C)(C)O)[C@H](O)[C@H](O3)C)[C@H](O)[C@H](O1)C)cc1cc(O[C@H]3C[C@@H](O[C@H]4C[C@H]([C@H](O)[C@H](O4)C)O)[C@@H](O)[C@H](O3)C)c(c(c1c2O)O)C,penetrating -C=12[C@@H]([C@H]([C@H](C=C2)C)CC[C@H](C[C@H](CC(=O)O)O)O)[C@H](C[C@@H](O)C1)OC([C@H](CC)C)=O,nonpenetrating +C=12[C@@H]([C@H]([C@H](C=C2)C)CC[C@H](C[C@H](CC(=O)O)O)O)[C@H](C[C@@H](O)C1)OC([C@H](CC)C)=O,non-penetrating c12[C@@H]3N(C(CN(C3)C(C3CCCCC3)=O)=O)CCc1cccc2,penetrating -c1(S(N(CCC)CCC)(=O)=O)ccc(C(O)=O)cc1,nonpenetrating +c1(S(N(CCC)CCC)(=O)=O)ccc(C(O)=O)cc1,non-penetrating c1(Cc2c(nc(N)nc2)N)cc(c(OC)c(c1)OC)OC,penetrating -c12c(ccc(CNc3cc(c(OC)c(c3)OC)OC)c1C)nc(N)nc2N,nonpenetrating -C(CO)(CO)(CO)N,nonpenetrating +c12c(ccc(CNc3cc(c(OC)c(c3)OC)OC)c1C)nc(N)nc2N,non-penetrating +C(CO)(CO)(CO)N,non-penetrating c12n(c3c(cc(F)cc3)F)cc(C(O)=O)c(c1cc(F)c(n2)N1C[C@@H]2C(N)[C@H]2C1)=O,penetrating C(N)(N)=O,penetrating -C=1(C2CCC(c3ccc(Cl)cc3)CC2)C(c2c(cccc2)C(C1O)=O)=O,nonpenetrating +C=1(C2CCC(c3ccc(Cl)cc3)CC2)C(c2c(cccc2)C(C1O)=O)=O,non-penetrating C1(C[C@@H]2N(C)[C@H](C1)CC2)OC([C@H](c1ccccc1)CO)=O,penetrating -C(CCCCCCCC(O)=O)(O)=O,nonpenetrating -O([C@H]1[C@@H]([C@@H](O[C@@H]2C[C@]([C@@H](O)[C@@H](O2)C)(OC)C)[C@@H](C(O[C@@H]([C@](C)(O)C([C@H]([N@@](C[C@@H](C[C@@]1(C)O)C)C)C)O)CC)=O)C)C)[C@H]1[C@@H]([C@H](C[C@H](O1)C)N(C)C)O,nonpenetrating -C([C@@H]1C(N[C@@H](Cc2c[nH]cn2)C(N[C@@H](C(N[C@H](C(=O)N[C@H](C(N[C@@H](C(N[C@H](C(N1)=O)[C@H](CC)C)=O)CCCN)=O)CCCCNC([C@@H](NC([C@H](NC([C@@H](NC([C@H]1N=C([C@@H]([C@@H](CC)C)N)SC1)=O)CC(C)C)=O)CCC(O)=O)=O)[C@H](CC)C)=O)CC(N)=O)=O)CC(O)=O)=O)=O)c1ccccc1,nonpenetrating -C([N+](C)(C)C)[C@@H](OC(N)=O)C,nonpenetrating -c1(c(cccc1)Br)C[N+](CC)(C)C,nonpenetrating -N12[C@](C3N(CCC3)C([C@@H]2CC(C)C)=O)(O[C@](C1=O)(NC([C@@H]1C=C2c3c4c(c(Br)[nH]c4ccc3)C[C@H]2[N@@](C1)C)=O)C(C)C)O,nonpenetrating +C(CCCCCCCC(O)=O)(O)=O,non-penetrating +O([C@H]1[C@@H]([C@@H](O[C@@H]2C[C@]([C@@H](O)[C@@H](O2)C)(OC)C)[C@@H](C(O[C@@H]([C@](C)(O)C([C@H]([N@@](C[C@@H](C[C@@]1(C)O)C)C)C)O)CC)=O)C)C)[C@H]1[C@@H]([C@H](C[C@H](O1)C)N(C)C)O,non-penetrating +C([C@@H]1C(N[C@@H](Cc2c[nH]cn2)C(N[C@@H](C(N[C@H](C(=O)N[C@H](C(N[C@@H](C(N[C@H](C(N1)=O)[C@H](CC)C)=O)CCCN)=O)CCCCNC([C@@H](NC([C@H](NC([C@@H](NC([C@H]1N=C([C@@H]([C@@H](CC)C)N)SC1)=O)CC(C)C)=O)CCC(O)=O)=O)[C@H](CC)C)=O)CC(N)=O)=O)CC(O)=O)=O)=O)c1ccccc1,non-penetrating +C([N+](C)(C)C)[C@@H](OC(N)=O)C,non-penetrating +c1(c(cccc1)Br)C[N+](CC)(C)C,non-penetrating +N12[C@](C3N(CCC3)C([C@@H]2CC(C)C)=O)(O[C@](C1=O)(NC([C@@H]1C=C2c3c4c(c(Br)[nH]c4ccc3)C[C@H]2[N@@](C1)C)=O)C(C)C)O,non-penetrating c12[C@]34[C@@]56[C@H]([N@@](CC7CC7)CC4)Cc2ccc(c1O[C@H]3[C@](OC)([C@H](C5)[C@](C(C)(C)C)(C)O)CC6)O,penetrating c1(C([C@@H](NC(C)(C)C)C)=O)cc(ccc1)Cl,penetrating O(S(C)(=O)=O)CCCCOS(C)(=O)=O,penetrating N12[C@@H]([C@@H](NC([C@H](c3ccccc3)C(=O)O)=O)[C-]2=O)SC([C@@H]1C(=O)O)(C)C,penetrating N(C(NCCCl)=O)(CCCl)N=O,penetrating -N12[C@H]([C@@H](NC([C@H](C=3CC=CCC3)N)=O)C1=O)SCC(=C2C(O)=O)C,nonpenetrating +N12[C@H]([C@@H](NC([C@H](C=3CC=CCC3)N)=O)C1=O)SCC(=C2C(O)=O)C,non-penetrating C1([C@H]([C@H](NC(C(Cl)Cl)=O)CO)O)CCC([N+](=O)=[O-])C[CH+]1,penetrating c12c(nccc1N[C@@H](CCCN(CC)CC)C)cc(Cl)cc2,penetrating -c12c(cc(Cl)c(c1)S(N)(=O)=O)N=CNS2(=O)=O,nonpenetrating +c12c(cc(Cl)c(c1)S(N)(=O)=O)N=CNS2(=O)=O,non-penetrating c1(c(cc(N)c(c1)Cl)OC)C(N[C@@H]1[C@H](C[N@@](CCCOc2ccc(F)cc2)CC1)OC)=O,penetrating n1(c2c(c(nc(n2)Cl)N)nc1)[C@@H]1O[C@H](CO)C(C1)O,penetrating -C(c1ccccc1)([C+]1CCCCC1)(C(O[C@@H]1C2CC[N+](C1)(C)CC2)=O)O,nonpenetrating -n1(c2c(nc3c1cccc3)cc(Nc1ccc(Cl)cc1)c(\c2)=N/C(C)C)c1ccc(Cl)cc1,nonpenetrating +C(c1ccccc1)([C+]1CCCCC1)(C(O[C@@H]1C2CC[N+](C1)(C)CC2)=O)O,non-penetrating 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-C1([C@@H](O[C@H]2O[C@@H]([C@@H](O)[C@@H]([C@H]2O)N)CO)[C@@H](C[C@@H]([C@H]1O[C@H]1O[C@@H]([C@@H](O)[C@@H]([C@H]1O)O)CN)N)N)O,nonpenetrating -c1([C@@]2(O[C@@H](COc3ccc(N4CCN(C(C)=O)CC4)cc3)CO2)Cn2ccnc2)c(cc(Cl)cc1)Cl,nonpenetrating +c1([C@]2(O[C@H](COc3ccc(N4CCN(c5ccc(n6c(n([C@@H](CC)C)nc6)=O)cc5)CC4)cc3)CO2)Cn2cncn2)c(cc(Cl)cc1)Cl,non-penetrating +C1([C@@H](O[C@H]2O[C@@H]([C@@H](O)[C@@H]([C@H]2O)N)CO)[C@@H](C[C@@H]([C@H]1O[C@H]1O[C@@H]([C@@H](O)[C@@H]([C@H]1O)O)CN)N)N)O,non-penetrating +c1([C@@]2(O[C@@H](COc3ccc(N4CCN(C(C)=O)CC4)cc3)CO2)Cn2ccnc2)c(cc(Cl)cc1)Cl,non-penetrating c1(cc(ccc1)[C@@H](C(O)=O)C)C(c1ccccc1)=O,penetrating -n12c([C@H](C(O)=O)CC2)ccc1C(c1ccccc1)=O,nonpenetrating +n12c([C@H](C(O)=O)CC2)ccc1C(c1ccccc1)=O,non-penetrating c12c3c(N4CCN(C)CC4)c(F)cc1c(c(C(O)=O)cn2[C@@H](C)CO3)=O,penetrating -O[C@@H]([C@@H]([C@@H](CO)O)O)[C@@H](CO)O,nonpenetrating -[C+](c1ccccc1)(c1ccccc1)(C(O[C@@H]1C[N+](CCC1)(C)C)=O)O,nonpenetrating -c1(cc(ccc1)O)[C@H]([C@H](C)N)O,nonpenetrating -c12c(ncc(n1)CN(c1ccc(C(N[C@@H](CCC(O)=O)C(O)=O)=O)cc1)C)nc(N)nc2N,nonpenetrating +O[C@@H]([C@@H]([C@@H](CO)O)O)[C@@H](CO)O,non-penetrating +[C+](c1ccccc1)(c1ccccc1)(C(O[C@@H]1C[N+](CCC1)(C)C)=O)O,non-penetrating +c1(cc(ccc1)O)[C@H]([C@H](C)N)O,non-penetrating +c12c(ncc(n1)CN(c1ccc(C(N[C@@H](CCC(O)=O)C(O)=O)=O)cc1)C)nc(N)nc2N,non-penetrating c1(ccc(CCOC)cc1)OC[C@@H](CNC(C)C)O,penetrating n1(c(cnc1C)[N+](=O)=[O-])CCO,penetrating -C1=2[C@H]([C@H]3[C@]([C@@](C#CC)(O)CC3)(C)C[C@@H]1c1ccc(N(C)C)cc1)CCC=1C2CCC(C1)=O,nonpenetrating +C1=2[C@H]([C@H]3[C@]([C@@](C#CC)(O)CC3)(C)C[C@@H]1c1ccc(N(C)C)cc1)CCC=1C2CCC(C1)=O,non-penetrating C1[C@@H]2[C@](C(=C3C(c4c(ccc(c4C[C@@H]13)N(C)C)O)=O)O)(C(C(C(N)=O)=C([C@H]2N(C)C)O)=O)O,penetrating c1(C(NCCN2CCOCC2)=O)ccc(Cl)cc1,penetrating -C1(c2c(Oc3c1cccc3)cccc2)C(OCC[N+](C(C)C)(C(C)C)C)=O,nonpenetrating +C1(c2c(Oc3c1cccc3)cccc2)C(OCC[N+](C(C)C)(C(C)C)C)=O,non-penetrating c1(cnccn1)C(N)=O,penetrating c1(OC(N(C)C)=O)c[n+](ccc1)C,penetrating c1(c2ccc(Cl)cc2)c(nc(N)nc1N)CC,penetrating -c12c([C@H]([C@H]3[N@@]4C[C@H](C=C)[C@H](C3)CC4)O)ccnc1ccc(c2)OC,nonpenetrating +c12c([C@H]([C@H]3[N@@]4C[C@H](C=C)[C@H](C3)CC4)O)ccnc1ccc(c2)OC,non-penetrating n1([C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)nc(C(N)=O)cn1,penetrating -C([C@@H](C[C@@H]([C@H](Cc1ccccc1)NC(OCc1cncs1)=O)O)NC([C@@H](NC(N(Cc1nc(C(C)C)sc1)C)=O)C(C)C)=O)c1ccccc1,nonpenetrating -C1[N@]([C@@H](C[C@@H]2CCCC[C@H]12)C(NC(C)(C)C)=O)C[C@H]([C@H](Cc1ccccc1)NC([C@@H](NC(c1nc2c(cccc2)cc1)=O)CC(N)=O)=O)O,nonpenetrating +C([C@@H](C[C@@H]([C@H](Cc1ccccc1)NC(OCc1cncs1)=O)O)NC([C@@H](NC(N(Cc1nc(C(C)C)sc1)C)=O)C(C)C)=O)c1ccccc1,non-penetrating +C1[N@]([C@@H](C[C@@H]2CCCC[C@H]12)C(NC(C)(C)C)=O)C[C@H]([C@H](Cc1ccccc1)NC([C@@H](NC(c1nc2c(cccc2)cc1)=O)CC(N)=O)=O)O,non-penetrating C(C(F)(F)F)(C(F)(F)F)OCF,penetrating -C1(C(C(C(I)[C-](C1I)NC(C)=O)C(=O)O)I)NC(C)=O,nonpenetrating +C1(C(C(C(I)[C-](C1I)NC(C)=O)C(=O)O)I)NC(C)=O,non-penetrating c1([C@@H](CNC(C)C)O)ccc(NS(C)(=O)=O)cc1,penetrating n1([C@@H]2O[C@H](CO)C=C2)c([nH]c(=O)c(c1)C)=O,penetrating -O([C@@H]1[C@]([C@H](C)O[C@H]1O[C@H]1[C@@H]([C@H]([C@H](NC(N)=[NH2])[C@H]([C@@H]1O)O)O)NC(N)=[NH2])(C=O)O)[C@H]1[C@H]([C@@H]([C@@H](O)[C@@H](O1)CO)O)NC,nonpenetrating +O([C@@H]1[C@]([C@H](C)O[C@H]1O[C@H]1[C@@H]([C@H]([C@H](NC(N)=[NH2])[C@H]([C@@H]1O)O)O)NC(N)=[NH2])(C=O)O)[C@H]1[C@H]([C@@H]([C@@H](O)[C@@H](O1)CO)O)NC,non-penetrating c1(S(Nc2ncccn2)(=O)=O)ccc(N)cc1,penetrating c1(S(Nc2c(c(C)no2)C)(=O)=O)ccc(N)cc1,penetrating c1(S(Nc2cc(C)on2)(=O)=O)ccc(N)cc1,penetrating @@ -297,120 +297,120 @@ N12[C@@H]([C@@H](NC([C@@H](c3ccsc3)C(=O)O)=O)C2=O)SC(C)(C)[C@@-]1C(=O)O,penetrat c12c(c(n3Cc4c(c3c2)nc2ccc(c(c2c4)CN(C)C)O)=O)COC([C@@]1(CC)O)=O,penetrating n1([C@@H]2O[C@H](CO)CC2)c(nc(N)cc1)=O,penetrating c12c(noc1cccc2)CS(N)(=O)=O,penetrating -C(=O)(O)[C@@H]1[C@@H]2O[C@@](C[C@H]1O)(O)C[C@H](O)C[C@H](O)[C@H](O)CC[C@H](O)C[C@@H](O)CC(=O)O[C@H](C)[C@H](C)[C@@H]([C@H](C=CC=CC=CC=CC=CC=CC=C[C@@H](C2)O[C@@H]1[C@@H](O)[C@H](N)[C@H]([C@@H](O1)C)O)C)O,nonpenetrating +C(=O)(O)[C@@H]1[C@@H]2O[C@@](C[C@H]1O)(O)C[C@H](O)C[C@H](O)[C@H](O)CC[C@H](O)C[C@@H](O)CC(=O)O[C@H](C)[C@H](C)[C@@H]([C@H](C=CC=CC=CC=CC=CC=CC=C[C@@H](C2)O[C@@H]1[C@@H](O)[C@H](N)[C@H]([C@@H](O1)C)O)C)O,non-penetrating C(=O)N1c2c(NC[C@H]1CNc1ccc(cc1)C(N[C@@H](CCC(=O)[O-])C([O-])=O)=O)nc(nc2O)N,penetrating [N-]12[C@H](SCC(=C1C(=O)[O-])C[n+]1ccccc1)[C@@H](C2=O)CC(\C(c1csc(n1)N)=N/OC(C(=O)O)(C)C)=O,penetrating c1cccc(c1)C[C@H](C)N,penetrating Nc1c(F)cnc(n1)O,penetrating -C1CCCC2(C1)O[C@H](CO2)CNC(N)=[NH2],nonpenetrating +C1CCCC2(C1)O[C@H](CO2)CNC(N)=[NH2],non-penetrating O=C(N(CCCl)N=O)NC1CCCCC1,penetrating -C(S([O-])(=O)=O)CS,nonpenetrating -O1[C@H]([C@H](NC(N(N=O)C)=O)[C@H]([C@@H]([C@H]1CO)O)O)O,nonpenetrating +C(S([O-])(=O)=O)CS,non-penetrating +O1[C@H]([C@H](NC(N(N=O)C)=O)[C@H]([C@@H]([C@H]1CO)O)O)O,non-penetrating O=C1[C@@H]2[C@H](c3c([C@@H]([C@H]2CO1)O[C@H]1O[C@@H]2[C@@H]([C@H]([C@@H]1O)O)O[C@H](OC2)c1cccs1)cc1c(c3)OCO1)c1cc(OC)c(c(c1)O)O,penetrating P(=S)(N1CC1)(N1CC1)N1CC1,penetrating -c12cc3cc(c1O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O[C@@H]1C[C@]([C@H]([C@@H](O1)C)O)(C)N)Oc1c(cc([C@H]([C@H](C(N[C@H](C(N[C@H]3C(N[C@H]3C(N[C@@H]([C@@H](c4cc(c(O2)cc4)Cl)O)C(N[C@H](C(O)=O)c2cc(O)cc(O)c2c2cc3ccc2O)=O)=O)=O)=O)CC(N)=O)=O)NC([C@H](NC)CC(C)C)=O)O)cc1)Cl,nonpenetrating +c12cc3cc(c1O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O[C@@H]1C[C@]([C@H]([C@@H](O1)C)O)(C)N)Oc1c(cc([C@H]([C@H](C(N[C@H](C(N[C@H]3C(N[C@H]3C(N[C@@H]([C@@H](c4cc(c(O2)cc4)Cl)O)C(N[C@H](C(O)=O)c2cc(O)cc(O)c2c2cc3ccc2O)=O)=O)=O)=O)CC(N)=O)=O)NC([C@H](NC)CC(C)C)=O)O)cc1)Cl,non-penetrating n1cnc2c(c1N)ncn2[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O,penetrating CN(C)CCCN1C2=CC=CC=C2SC3=C1C=C(C=C3)C(F)(F)F,penetrating c1(NCCSCc2oc(cc2)CN(C)C)[nH]cc(c1N(=O)=O)Cc1ccccc1,penetrating -c12c(C(N(Cc3n1cnc3c1noc(n1)C(CO)(CO)C)C)=O)c(ccc2)Cl,nonpenetrating +c12c(C(N(Cc3n1cnc3c1noc(n1)C(CO)(CO)C)C)=O)c(ccc2)Cl,non-penetrating Cc1nc(sc1)\[NH]=C(\N)N,penetrating -c12c(C(N(Cc3n1cnc3c1noc(n1)C(O)(C)C)C)=O)c(ccc2)Cl,nonpenetrating +c12c(C(N(Cc3n1cnc3c1noc(n1)C(O)(C)C)C)=O)c(ccc2)Cl,non-penetrating C1C(CCN(C1)C(NC1CCCCC1)=S)c1c[nH]cn1,penetrating -C([C@@](C(O)=O)(NN)C)c1cc(c(O)cc1)O,nonpenetrating -c1(ccc(O)c(c1)O)CCN,nonpenetrating +C([C@@](C(O)=O)(NN)C)c1cc(c(O)cc1)O,non-penetrating +c1(ccc(O)c(c1)O)CCN,non-penetrating c1(c(ccc(c1)C[C@@H](C(O)=O)N)O)O,penetrating c12c(c(cc(n2)C(F)(F)F)[C@@H]([C@H]2CCCCN2)O)cccc1C(F)(F)F,penetrating c12c3c(N4CCN(C)CC4)c(F)c(c1c(ccn2[C@H](C)CO3)=O)C(O)=O,penetrating c1(ccc2C(=NC[C@@H](N(C)c2c1)CNC(c1ccc(cc1)C)=O)c1ccc(cc1)F)C,penetrating -C1C(C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@H](CC2)C(CO)=O)C=O)C)=O,nonpenetrating +C1C(C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@H](CC2)C(CO)=O)C=O)C)=O,non-penetrating C[N@]1CCc2cccc3c2[C@@H]1Cc1ccc(O)c(O)c31,penetrating -c1ccc2c(c1)n(c(n2)NC1CCN(CC1)CCc1ccc(cc1)OC)Cc1ccc(cc1)F,nonpenetrating +c1ccc2c(c1)n(c(n2)NC1CCN(CC1)CCc1ccc(cc1)OC)Cc1ccc(cc1)F,non-penetrating c1(cc(c(cc1)Cl)Cl)CC(N1CCCC[C@H]1CN1CCCC1)=O,penetrating c1(cc(c(cc1)Cl)Cl)CC(N1[C@@H](c2c(CC1)cccc2)CN1CCCC1)=O,penetrating c1(ccc(cc1)C(F)(F)F)CC(N1[C@@H](CCCC1)CN1CCCC1)=O,penetrating c1(ccc(c(c1)Cl)Cl)CC(N1[C@@H](c2c(CC1)scc2)CN1CCCC1)=O,penetrating -c1(ccc(c(c1)Cl)Cl)CC(N1[C@@H](c2c(CC1)[nH]cn2)CN1CCCC1)=O,nonpenetrating +c1(ccc(c(c1)Cl)Cl)CC(N1[C@@H](c2c(CC1)[nH]cn2)CN1CCCC1)=O,non-penetrating c1(ccc(c(c1)Cl)Cl)CC(N1[C@@H](c2c(CC1)ccs2)CN1CCCC1)=O,penetrating c1(ccc(c(c1)Cl)Cl)CC(N1[C@@H](CN2CCCC2)CC(CC1)(C)C)=O,penetrating -CC(C)(C(O)=O)c1ccc(cc1)C(=O)CCCN1CCC(CC1)OC(c1ccccc1)c1ccccc1,nonpenetrating -c1c(ccc([C@@H](c2ccccc2)N2CCN(CC2)CCOCC(=O)O)c1)Cl,nonpenetrating -c1(c(cc2c(c1)n(cc(c2=O)C(O)=O)C1CC1)F)N1CCNCC1,nonpenetrating -C1C(C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@H]1O)([C@H](CC2)C(CO)=O)C)C)=O,nonpenetrating -C1C(C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(CO)=O)O)C)C)=O,nonpenetrating -c1cn(CCO)c(CC)c(O)c1=O,nonpenetrating -c1cn(CCCCO)c(CC)c(O)c1=O,nonpenetrating +CC(C)(C(O)=O)c1ccc(cc1)C(=O)CCCN1CCC(CC1)OC(c1ccccc1)c1ccccc1,non-penetrating +c1c(ccc([C@@H](c2ccccc2)N2CCN(CC2)CCOCC(=O)O)c1)Cl,non-penetrating +c1(c(cc2c(c1)n(cc(c2=O)C(O)=O)C1CC1)F)N1CCNCC1,non-penetrating +C1C(C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@H]1O)([C@H](CC2)C(CO)=O)C)C)=O,non-penetrating +C1C(C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(CO)=O)O)C)C)=O,non-penetrating +c1cn(CCO)c(CC)c(O)c1=O,non-penetrating +c1cn(CCCCO)c(CC)c(O)c1=O,non-penetrating c1cn(c(c(c1=O)O)C)C,penetrating c1cn(CC)c(c(c1=O)O)C,penetrating c1cn(CCCC)c(C)c(O)c1=O,penetrating c1cn(CCCCCC)c(C)c(O)c1=O,penetrating c1cn(CCCCC)c(C)c(O)c1=O,penetrating -c1cn(CCCO)c(C)c(O)c1=O,nonpenetrating +c1cn(CCCO)c(C)c(O)c1=O,non-penetrating c1cn(CC)c(CC)c(c1=O)O,penetrating C[C@]12c3c(C[C@H]([C@H]1C)[N@](CC2)CC1CC1)ccc(c3)O,penetrating -CN1CCN(CC1)c1cc2n(cc(C(O)=O)c(=O)c2cc1F)c1ccc(F)cc1,nonpenetrating +CN1CCN(CC1)c1cc2n(cc(C(O)=O)c(=O)c2cc1F)c1ccc(F)cc1,non-penetrating O(C(c1ccccc1)c1ccccc1)CCN(C)C,penetrating CN(C)CCO[C@@](C)(c1ccccc1)c1ccccn1,penetrating -c1ccc([C@H](C[N@]2CC[C@H](C2)O)N(C(Cc2ccccc2N)=O)C)cc1,nonpenetrating -c1(c(cc2c(n1)n(cc(c2=O)C(O)=O)CC)F)N1CCNCC1,nonpenetrating +c1ccc([C@H](C[N@]2CC[C@H](C2)O)N(C(Cc2ccccc2N)=O)C)cc1,non-penetrating +c1(c(cc2c(n1)n(cc(c2=O)C(O)=O)CC)F)N1CCNCC1,non-penetrating c1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C,penetrating -CN1CCN(CC1)c1c(F)cc2c(=O)c(cn(CCF)c2c1F)C(O)=O,nonpenetrating +CN1CCN(CC1)c1c(F)cc2c(=O)c(cn(CCF)c2c1F)C(O)=O,non-penetrating OCCN1CCN(CC\C=C2/c3ccccc3Sc3ccc(cc23)C(F)(F)F)CC1,penetrating -C(=O)(O)c1c(NCc2ccco2)cc(c(c1)S(N)(=O)=O)Cl,nonpenetrating +C(=O)(O)c1c(NCc2ccco2)cc(c(c1)S(N)(=O)=O)Cl,non-penetrating c1(cc(c(cc1)Cl)Cl)CC(N1[C@@H](CN2CCCC2)CN(CC1)C(=O)C)=O,penetrating c1(ccc(c(c1)Cl)Cl)CC(N1[C@@H](c2c(CC1)occ2)CN1CCCC1)=O,penetrating c1(ccc(c(c1)Cl)Cl)CC(N1[C@H](CN(CC1)C(=O)OC)CN1CCCC1)=O,penetrating c1(ccc(c(c1)Cl)Cl)CC(N1[C@H](CN(CC1)C(=O)OCC)CN1CCCC1)=O,penetrating c1(CC(N2[C@H](CN(CC2)C(=O)OCCC)CN2CCCC2)=O)cc(c(cc1)Cl)Cl,penetrating c1(ccc(c(c1)Cl)Cl)CC(N1[C@@H](c2c(CC1)occ2)C[N@@]1C[C@@H](CC1)O)=O,penetrating -c1(ccc(c(c1)Cl)Cl)CC(=O)N1[C@H](CN(C(=O)C)CC1)C[N@@]1C[C@H](O)CC1,nonpenetrating -c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](C2)O)=O)ccc(C(F)(F)F)cc1,nonpenetrating -c1(ccc(cc1)SC)CC(N1[C@H](CN(CC1)C(=O)C)C[N@]1CC[C@H](C1)O)=O,nonpenetrating -c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](C2)O)=O)cc(cc(c1)F)F,nonpenetrating -c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](C2)O)=O)cc(ccc1)OC,nonpenetrating -c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](O)C2)=O)ccc(N(=O)=O)cc1,nonpenetrating -c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](C2)O)=O)ccc(OC)cc1,nonpenetrating -c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](O)C2)=O)cc(ccc1)N(=O)=O,nonpenetrating -c1(ccccc1)CC(N1[C@H](CN(CC1)C(=O)C)C[N@]1CC[C@H](C1)O)=O,nonpenetrating -c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](O)C2)=O)ccc([S@](=O)C)cc1,nonpenetrating -c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](O)C2)=O)ccc(S(=O)(=O)C)cc1,nonpenetrating +c1(ccc(c(c1)Cl)Cl)CC(=O)N1[C@H](CN(C(=O)C)CC1)C[N@@]1C[C@H](O)CC1,non-penetrating +c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](C2)O)=O)ccc(C(F)(F)F)cc1,non-penetrating +c1(ccc(cc1)SC)CC(N1[C@H](CN(CC1)C(=O)C)C[N@]1CC[C@H](C1)O)=O,non-penetrating +c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](C2)O)=O)cc(cc(c1)F)F,non-penetrating +c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](C2)O)=O)cc(ccc1)OC,non-penetrating +c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](O)C2)=O)ccc(N(=O)=O)cc1,non-penetrating +c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](C2)O)=O)ccc(OC)cc1,non-penetrating +c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](O)C2)=O)cc(ccc1)N(=O)=O,non-penetrating +c1(ccccc1)CC(N1[C@H](CN(CC1)C(=O)C)C[N@]1CC[C@H](C1)O)=O,non-penetrating +c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](O)C2)=O)ccc([S@](=O)C)cc1,non-penetrating +c1(CC(N2[C@H](CN(CC2)C(=O)C)C[N@]2CC[C@H](O)C2)=O)ccc(S(=O)(=O)C)cc1,non-penetrating CC(C)[C@@H](N(C)C(=O)Cc1ccc(c(c1)Cl)Cl)CN1CCCC1,penetrating c1(ccccc1)[C@H](CN1CCCC1)N(C(=O)Cc1ccc(c(c1)Cl)Cl)C,penetrating -CN1C(=C(O)c2ccccc2S1(=O)=O)C(=O)Nc1cc(C)on1,nonpenetrating +CN1C(=C(O)c2ccccc2S1(=O)=O)C(=O)Nc1cc(C)on1,non-penetrating c1cc2c(cc1O)[C@]13[C@@H]([C@@H](C2)[N@@](CC=C)CC3)CCCC1,penetrating -CCn1cc(C(O)=O)c(=O)c2cc(F)c(N3CCN[C@H](C)C3)c(F)c12,nonpenetrating -CN(C)C(=O)C(CCN1CCC(O)(CC1)c1ccc(Cl)cc1)(c1ccccc1)c1ccccc1,nonpenetrating -C1Cc2c(\C(c3c1cc(cc3)Cl)=C1/CCN(CC1)C(=O)OCC)nccc2,nonpenetrating -CN1C(=C(O)c2ccccc2S1(=O)=O)C(=O)Nc1ncc(C)s1,nonpenetrating +CCn1cc(C(O)=O)c(=O)c2cc(F)c(N3CCN[C@H](C)C3)c(F)c12,non-penetrating +CN(C)C(=O)C(CCN1CCC(O)(CC1)c1ccc(Cl)cc1)(c1ccccc1)c1ccccc1,non-penetrating +C1Cc2c(\C(c3c1cc(cc3)Cl)=C1/CCN(CC1)C(=O)OCC)nccc2,non-penetrating +CN1C(=C(O)c2ccccc2S1(=O)=O)C(=O)Nc1ncc(C)s1,non-penetrating c12[C@@]34[C@H]5[C@@H]([N@](CC=C)CC4)Cc2ccc(c1O[C@@H]3[C@@H](O)C=C5)O,penetrating c12[C@@]34[C@]5([C@@H]([N@](CC6CC6)CC4)Cc2ccc(c1O[C@@H]3C(=O)CC5)O)O,penetrating -c1(c(cc2c(c1)n(cc(c2=O)C(O)=O)CC)F)N1CCNCC1,nonpenetrating -CCn1cc(C(O)=O)c(=O)c2cc(F)c(cc12)N1CCN(C)CC1,nonpenetrating +c1(c(cc2c(c1)n(cc(c2=O)C(O)=O)CC)F)N1CCNCC1,non-penetrating +CCn1cc(C(O)=O)c(=O)c2cc(F)c(cc12)N1CCN(C)CC1,non-penetrating c12c(Sc3c(N1CCCN1CCN(CC1)CCO)cc(cc3)Cl)cccc2,penetrating -c1ccc2c(c1)C(=C(N(S2(=O)=O)C)C(Nc1ncccc1)=O)O,nonpenetrating +c1ccc2c(c1)C(=C(N(S2(=O)=O)C)C(Nc1ncccc1)=O)O,non-penetrating C1[C@H]2[C@H]([C@H]3[C@]([C@@H](C(C)=O)CC3)(C)C1)CCC=1[C@@]2(CCC(C1)=O)C,penetrating Oc1ccc2[nH]cc(CCCC[N@@]3CCC(=CC3)c3ccccc3)c2c1,penetrating c1ccc2N([C@H](CN3CCCC3)C)c3c(ccc(C(=O)NCCC)c3)Sc2c1,penetrating -CN1CCN(CC1)c1c(F)cc2c(=O)c(cn3CCSc1c23)C(O)=O,nonpenetrating -CC(C)(C)NC[C@@H](O)c1ccc(O)c(CO)c1,nonpenetrating +CN1CCN(CC1)c1c(F)cc2c(=O)c(cn3CCSc1c23)C(O)=O,non-penetrating +CC(C)(C)NC[C@@H](O)c1ccc(O)c(CO)c1,non-penetrating c1(ccc(c(c1)Cl)Cl)CC(=O)N1[C@H](C[N@@](C)CC1)CN1CCCC1,penetrating c1(ccc(c(c1)Cl)Cl)CC(N1[C@H](CN2CCCC2)c2n(CC1)ccn2)=O,penetrating -c1(ccc(c(c1)Cl)Cl)CC(N1[C@H](C[C@]2(CC1)NC(NC2=O)=O)CN1CCCC1)=O,nonpenetrating -c1(ccc(c(c1)Cl)Cl)CC(N1[C@H](C[C@]2(CC1)C(NC(N2)=O)=O)CN1CCCC1)=O,nonpenetrating -c1(ccc(c(c1)Cl)Cl)CC(N1[C@H](C[N@@]2C[C@@H](CC2)O)c2n(CC1)ccn2)=O,nonpenetrating +c1(ccc(c(c1)Cl)Cl)CC(N1[C@H](C[C@]2(CC1)NC(NC2=O)=O)CN1CCCC1)=O,non-penetrating +c1(ccc(c(c1)Cl)Cl)CC(N1[C@H](C[C@]2(CC1)C(NC(N2)=O)=O)CN1CCCC1)=O,non-penetrating +c1(ccc(c(c1)Cl)Cl)CC(N1[C@H](C[N@@]2C[C@@H](CC2)O)c2n(CC1)ccn2)=O,non-penetrating c1(ccc(c(c1)Cl)Cl)CC(N1[C@H](CN2CCCC2)c2n(CC1)ncn2)=O,penetrating -c1(ccc(c(c1)Cl)Cl)CC(N1[C@@H](C[N@@]2C[C@@H](CC2)O)C[N@](CC1)CCO)=O,nonpenetrating -c1(ccc(c(c1)Cl)Cl)CC(N1[C@H](C[N@@]2C[C@@H](CC2)O)c2c(CC1)[nH]cn2)=O,nonpenetrating +c1(ccc(c(c1)Cl)Cl)CC(N1[C@@H](C[N@@]2C[C@@H](CC2)O)C[N@](CC1)CCO)=O,non-penetrating +c1(ccc(c(c1)Cl)Cl)CC(N1[C@H](C[N@@]2C[C@@H](CC2)O)c2c(CC1)[nH]cn2)=O,non-penetrating c1ccc2nc(c(c(C(N[C@@H](CC)c3ccccc3)=O)c2c1)O)c1ccccc1,penetrating c1cc2c(C(N[C@@H](CC)c3ccccc3)=O)c(c(nc2cc1)c1ccccc1)OCCCN(C)C,penetrating -c1cc2c(C(N[C@@H](CC)c3ccccc3)=O)c(c(nc2cc1)c1ccccc1)OCC(O)=O,nonpenetrating -c1cc2c(C(N[C@@H](CC)c3ccccc3)=O)c(c(c3ccccc3)nc2cc1)OCCCC(O)=O,nonpenetrating -c1ccc2c(c(C(N[C@@H](CC)c3ccccc3)=O)c(OCCNC(Cc3c(cccc3)C(=O)O)=O)c(c3ccccc3)n2)c1,nonpenetrating -c1cc2c(c(OCCNC(Cc3ncccc3)=O)c(c3ccccc3)nc2cc1)C(N[C@@H](CC)c1ccccc1)=O,nonpenetrating -c1cc2c(c(c(c3ccccc3)nc2cc1)OCCNC([C@@H]1CCCN1)=O)C(=O)N[C@@H](CC)c1ccccc1,nonpenetrating -c1cc2c(C(N[C@@H](CC)c3ccccc3)=O)c(c(nc2cc1)c1ccccc1)Cn1cncc1,nonpenetrating -c1(c(c(c2c(c1F)n(cc(c2=O)C(O)=O)C1CC1)N)F)N1C[C@@H](N[C@@H](C1)C)C,nonpenetrating +c1cc2c(C(N[C@@H](CC)c3ccccc3)=O)c(c(nc2cc1)c1ccccc1)OCC(O)=O,non-penetrating +c1cc2c(C(N[C@@H](CC)c3ccccc3)=O)c(c(c3ccccc3)nc2cc1)OCCCC(O)=O,non-penetrating +c1ccc2c(c(C(N[C@@H](CC)c3ccccc3)=O)c(OCCNC(Cc3c(cccc3)C(=O)O)=O)c(c3ccccc3)n2)c1,non-penetrating +c1cc2c(c(OCCNC(Cc3ncccc3)=O)c(c3ccccc3)nc2cc1)C(N[C@@H](CC)c1ccccc1)=O,non-penetrating +c1cc2c(c(c(c3ccccc3)nc2cc1)OCCNC([C@@H]1CCCN1)=O)C(=O)N[C@@H](CC)c1ccccc1,non-penetrating +c1cc2c(C(N[C@@H](CC)c3ccccc3)=O)c(c(nc2cc1)c1ccccc1)Cn1cncc1,non-penetrating +c1(c(c(c2c(c1F)n(cc(c2=O)C(O)=O)C1CC1)N)F)N1C[C@@H](N[C@@H](C1)C)C,non-penetrating CCNCc1c(CSC)cnc(C)c1O,penetrating -CN1C(=C(O)c2sccc2S1(=O)=O)C(=O)Nc1ccccn1,nonpenetrating -CC(C)(C)c1ccc(cc1)[C@H](O)CCCN1CCC(CC1)C(O)(c1ccccc1)c1ccccc1,nonpenetrating +CN1C(=C(O)c2sccc2S1(=O)=O)C(=O)Nc1ccccn1,non-penetrating +CC(C)(C)c1ccc(cc1)[C@H](O)CCCN1CCC(CC1)C(O)(c1ccccc1)c1ccccc1,non-penetrating C1C(C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)O)C)C)=O,penetrating C1CC[C@H]([C@@H](N(C(Cc2ccc(c(c2)Cl)Cl)=O)C)C1)N1CCCC1,penetrating diff --git a/classification/kazius.csv b/classification/kazius.csv index 3297a15..1c14d94 100644 --- a/classification/kazius.csv +++ b/classification/kazius.csv @@ -1,4070 +1,4070 @@ SMILES,Mutagenicity -COC1=CC=C(C=C1)C2=NC(=C([NH]2)C3=CC=CC=C3)C4=CC=CC=C4,active -CC1=C(C=CC=C1N=C=O)N=C=O,active -OCCC1=C[N](N=O)C2=CC=CC=C12,active -[O-][N+](=O)C1=CC(=CS1)C(=O)NC2=CC(=CC=C2)Br,active -CN(N=O)C1=CC=CC=C1,active -CN2C1=C(C=CC=C1)C(=O)C3=C2C4=C(C=C3O)OC(C4)C5(C)CO5,active -CS(=O)(=O)NC1=CC=C(C=C1)NC3=C2C=CC=CC2=NC4=CC=CC=C34,active -[O-][N+](=O)C1=CC=C(C=C1)OC2=C(C=C(C=C2)Cl)Cl,active -OC1=C(C=CC(=C1)[N+]([O-])=O)[N+]([O-])=O,active -C[N]2C(=NC3=C1N=CC=NC1=C(C)C(=C23)C)N,active -CSC1=C(C(=C(C(=C1)SC)N)C)N,active -OC1=CC4=C(C=C1)C3=CC2=CC=CC=C2C=C3C5=CC=CC=C45,active -CC(=O)C(Br)=C,active -NCCNCCNCCN,active -CN(C)C1=CC=C(C=C1)CCO,active -COC4=CC(=O)C3=C2[NH]C1=CC=NC=C1C2=CN=C3C4=O,active -N1C3C1C2=CSC=C2C4=CSC=C34,active -CC1=C(C=C(C(=C1)N=NC2=CC=CC=C2)N)N,active -NC3=CC2=NC1=CC(=CC=C1C=C2C=C3)N,active -[O-][N+](=O)C3=C1CCC2=CC=CC(=C12)C=C3,active -NC1=CC=C(C=C1)C=CC2=CC=C(C=C2)[N+]([O-])=O,active -COC(=O)C1(OC1(C)C(O)C(C)C)C(N)=O,active -CC(I)C1OCC(CO)O1,active -CN(C)CCNC(=O)C3=C2N=C1C=CC=CC1=NC2=CC=C3,active -CC1=C(C=C(C=C1)N)C,active -CC1=C3C(=CC=N1)C2=CC=CC=C2[NH]3,active -OC1CN(CCO1)N=O,active -[O-][N+](=O)C1=C(C=CC=C1)C(Cl)=O,active -ClCCOP(OCCCl)OCCCl,active -COC(=O)NC2=NC1=CC=CC=C1[NH]2,active -CCOC(=O)N(CCCC(=O)C1=CN=CC=C1)N=O,active -C1CSCCS1,active -NC1=CC=C(C=C1)C2=CC=C(C=C2)Cl,active -NNC2=C1C=CC=CC1=C(N=N2)NN,active -C[N]3C(=NC4=CC=C2C=CC1=CC=C(O)C=C1C2=C34)C,active -CC(=O)OC1=CC=C(C=C1)CCl,active -NC1=CC=C(C=C1)OC2=CC=C(C=C2)[N+]([O-])=O,active 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