Journal of molecular modeling

Supplementary material

COMPASS II: Extended Coverage for Polymer and Drug-like Molecule Databases

Huai Sun*,1, Zhao Jin1, Chunwei Yang1, Reinier L. C. Akkermans2, Struan H. Robertson2, Neil A. Spenley2, Simon Miller 2†, Stephen M. Todd2

1 School of Chemistry and Chemical Engineering and Key Laboratory of Scientific and Engineering Computing of Ministry of Education, Shanghai Jiao Tong University, Shanghai 200240, China.

2 Dassault Systèmes BIOVIA, 334 Cambridge Science Park, Cambridge, CB4 0WN, United Kingdom

*Corresponding author’s e-mail:

Molecule training sets separated into three parts for A) small molecules composing with one functional group, B) molecules containing two or more functional groups and C) molecules from Maybridge screening collection for validation. All molecule names are shown following SMILE format.

Training Set A

Name / Conform
CC / 13
CCC / 23
CCCC / 23
CC(C)C / 13
CCCCC / 34
CC(C)(C)C / 11
C / 1
CC=CC / 12
CC(C)=C / 11
C=C / 1
CC=C / 7
CC(C)=C(C)C / 5
C#C / 1
CC#C / 1
CC#CC / 1
c1ccccc1 / 1
CCc1ccccc1 / 10
C=Cc1ccccc1 / 4
Cc1cccc(C)c1 / 5
Cc1ccccc1C / 1
Cc1ccc(C)cc1 / 9
Cc1ccccc1 / 5
Cc1cccc2ccccc12 / 4
c2ccc1ccccc1c2 / 1
c3ccc2cc1ccccc1cc2c3 / 1
c1ccc2c(c1)ccc3ccccc23 / 1
c1cc2ccc3cccc4ccc(c1)c2c34 / 1
c1ccc3c(c1)c2ccccc2c4ccccc34 / 1
c1cc2ccc3cc5cccc6ccc4cc(c1)c2c3c4c56 / 1
c1cc2ccc3ccc4ccc5ccc6ccc1c7c2c3c4c5c67 / 1
c1cc2cc3ccc4cc5cccc6cc7ccc8cc(c1)c2c9c3c4c(c56)c7c89 / 1
c2ccc1ccccc1c2 / 1
CCCO / 24
CC(C)O / 24
CCO / 18
CO / 7
Oc1ccccc1 / 8
CC(C)(C)O / 30
COC / 30
CCOC / 28
CCOCC / 22
COC(C)C / 23
CCOC(C)C / 24
COC(C)(C)C / 22
CC(C)OC(C)C / 15
CCOC(C)(C)C / 24
CC(C)OC(C)(C)C / 18
CC(C)(C)OC(C)(C)C / 14
CC=O / 6
CCC=O / 16
CC(C)=O / 6
CCCC=O / 24
CCC(C)=O / 21
O=Cc1ccccc1 / 8
CC(=O)c1ccccc1 / 12
C=O / 1
CCC(O)=O / 5
OC(=O)c1ccccc1 / 7
COC(C)=O / 9
CC(O)=O / 5
OC=O / 12
OC(=O)C=C / 7
COC=O / 7
O=COc1ccccc1 / 10
CCOC=O / 10
Nc1ccccc1 / 13
CNC / 13
CCN / 25
CN / 13
CCCN / 22
CN(C)C / 24
CN(C)C(C)=O / 16
NC=O / 4
CNC=O / 22
O=CNc1ccccc1 / 30
CNC(O)=O / 38
OC(=O)Nc1ccccc1 / 43
OC(O)=O / 17
COC(=O)OC / 18
OC(=O)Oc1ccccc1 / 16
CCCCF / 16
CC(F)F / 6
FCC(F)(F)F / 7
FC(F)C(F)F / 6
FCCF / 6
FCF / 1
Fc1ccccc1 / 1
CCF / 6
CF / 1
CCCF / 9
Fc1ccccc1F / 1
Fc1ccc(F)cc1 / 1
FC(F)(F)C(F)(F)F / 4
FC(F)(F)F / 1
FC(F)F / 1
ClC(Cl)(Cl)C(Cl)(Cl)Cl / 5
ClC(Cl)C(Cl)Cl / 4
CC(Cl)Cl / 5
ClCCCl / 5
ClCC(Cl)CCl / 5
ClCCCCl / 7
CCCCl / 6
CCCCCl / 6
ClC(Cl)(Cl)Cl / 1
ClCCl / 1
ClCC(Cl)(Cl)Cl / 4
CCl / 1
ClC(Cl)Cl / 1
CCCBr / 6
CCCCBr / 6
BrC(Br)C(Br)Br / 4
CCBr / 7
BrCBr / 1
CBr / 1
CC(Br)Br / 6
BrC(Br)Br / 1
CC(C)(C)I / 7
ICCI / 5
CCI / 7
ICI / 1
CI / 1
IC(I)I / 1
CCCI / 6
FC(F)(F)C(Cl)Br / 1
CC(F)(F)Cl / 1
FC(F)(Cl)C(F)(Cl)Cl / 1
FC(Cl)(Cl)C(F)(Cl)Cl / 1
FC(F)(F)C(F)(Br)Br / 1
FC(F)(Cl)C(F)(F)Cl / 1
ClCBr / 1
FC(F)(F)Br / 1
ClC(Cl)(Cl)Br / 1
FC(F)Cl / 1
FCCl / 1
FC(F)(F)Cl / 1
FC(F)(Br)Br / 1
FC(F)(Cl)Cl / 1
FC(Cl)(Cl)Cl / 1
C1CO1 / 1
C1CS1 / 1
C1CN1 / 1
C1CC1 / 1
C1COC1 / 1
C1CNC1 / 1
FC1(F)C(F)(F)C(F)(F)C1(F)F / 1
C1CCC1 / 1
C1CCSC1 / 1
C1CCNC1 / 1
C1CCCC1 / 1
C1CCOCC1 / 1
C1CCSCC1 / 1
C1CCNCC1 / 1
C1CCCCC1 / 1
o1cccc1 / 1
s1cccc1 / 1
n1cccc1 / 1
n2c1ccccc1c3ccccc23 / 1
n1ccnc1 / 1
o1ccnc1 / 1
s1ccnc1 / 1
c1ccncc1 / 1
c2ccc1cnccc1c2 / 1
c1cncnc1 / 1
c2ccc1ncccc1c2 / 1
s1cccc1 / 1
O=C1CC1 / 1
O=C1CCC1 / 1
O=C1CCCC1 / 1
O=C1CCCCC1 / 1
C1OC=C1 / 1
C1NC=C1 / 1
C1CC=C1 / 1
C1OCC=C1 / 1
C1SCC=C1 / 1
C1NCC=C1 / 1
C1C=CC=C1 / 1
C1CC=CC1 / 1
C12C3C4C1C5C2C3C45 / 1
C1CC2CCC1C2 / 1
C1CC2C3C4C1C5C2C3C45 / 1
C1CC2CCC1CC2 / 1
C1C3CC2CC1CC(C2)C3 / 1
N=C=O / 1
CN=C=O / 5
CC#N / 1
N#Cc1ccccc1 / 1
C#N / 1
O=N(=O)c1ccccc1 / 5
O=N=O / 1
O=C=O / 1
S / 1
O=N=O / 1
N=O / 1
CN(C)(C)=O / 5
O=Nc1ccccc1 / 6
CCN / 10
CN1C=CN(C)=C1 / 1
CN1C=CC=CC=1 / 1
CN / 5
O / 1
N / 1
OC(=O)c1ccccc1 / 5
Sc1ccccc1 / 1
CSC(C)(C)C / 10
CSC(C)C / 10
CCSCC / 10
CSC / 13
CCS / 13
CC(C)(C)S / 13
CCCS / 13
CC(C)S / 13
CS / 13
S1SSSSS1 / 1
CS(C)(=O)=O / 7
CS(=O)(=O)c1ccccc1 / 6
OS(=O)(=O)c1ccccc1 / 7
OS(=O)=O / 1
OS(O)(=O)=O / 1
OS(=O)(=O)c1ccccc1 / 13
CCCP / 12
Pc1ccccc1 / 13
ClP1(Cl)N=P(Cl)(Cl)N=P(Cl)(Cl)N=1 / 1
FP1(F)N=P(F)(F)N=P(F)(F)N=1 / 1
SiSi / 3
SiSi(Si)Si / 3
SiSiSiSi / 7
Si / 1
CSi(C)(Si)Si / 6
CSiC / 3
CCSiSi / 7
CCSi / 3
CSiSi / 3
SiSic1ccccc1 / 4
OSi15OSi3(O)OSi2(O)OSi(O)(O1)OSi4(O)OSi(O)(O2)OSi(O)(O3)OSi(O)(O4)O5 / 1
SiOSi / 6
OSic1ccccc1 / 4
O1SiOSiOSi1 / 1
O=COC=O / 26
c1ccc(cc1)c2ccc(cc2)c3ccccc3 / 1
c1ccc(cc1)c2cc(cc(c2)c3ccccc3)c4ccccc4 / 1
c1ccc(cc1)c2ccccc2 / 7
OCC(O)CO / 1
OCCCO / 1
OCCO / 10
CP(C)=N / 7
OC(=O)c1ccccc1 / 5
O=c1ccccc1 / 1
CCCO / 1
CCOS(O)(=O)=O / 15
OS(=O)(=O)c1ccccc1 / 7
OS(=O)(=O)C(F)(F)F / 4
COS(O)(=O)=O / 9
OS(=O)=O / 1
OS(O)(=O)=O / 1
OS(=O)(=O)c1ccccc1 / 13
OS(=O)(=O)c1ccccc1 / 4
o1cccc1 / 1
s1cccc1 / 1
n1cccc1 / 1
n2c1ccccc1c3ccccc23 / 1
n1ccnc1 / 1
o1ccnc1 / 1
s1ccnc1 / 1
c1ccncc1 / 1
c2ccc1cnccc1c2 / 1
c1cncnc1 / 1
c2ccc1ncccc1c2 / 1
s1cccc1 / 1
CN(C)(C)=O / 1
CN1C=CN(C)=C1 / 1
CN1C=CC=CC=1 / 1
CN / 5
O / 1
N / 1
FAs(F)(F)(F)(F)F / 2
FB(F)(F)F / 1
CCOS(O)(=O)=O / 15
N#CNC#N / 1
OS(=O)(=O)C(F)(F)F / 4
COS(O)(=O)=O / 9
Cl / 1
OCl(=O)(=O)=O / 1
ClIn(Cl)(Cl)Cl / 2
FP(F)(F)(F)(F)F / 1
OS(=O)(=O)c1ccccc1 / 4
CN(C)(C)C / 5
CCP(C)(C)C / 13
CN1(C)CCCC1 / 1
CCN1(C)CCCC1 / 19
CCN1C=CC=CC=1 / 4
CCN1C=CC=C(C)C=1 / 5
C1C=CN=CC=1 / 1
CCOC(=O)C1=CC=CN=C1 / 16
CN1C=CN(C)=C1 / 6
OCl(=O)(=O)=O / 1
NC(N)=N / 1
COC(=O)CS(O)(=O)=O / 17
FC(F)(F)S(=O)(=O)CS(=O)=O / 1
ClIn(Cl)(Cl)Cl / 2
ON(=O)=O / 1
OS(=O)=NS(=O)(=O)C(F)(F)F / 15
FP(F)(F)(F)(F)F / 2
OS(=O)(=O)c1ccccc1 / 4
FAs(F)(F)(F)(F)F / 2
FB(F)(F)F / 1
COP(O)(=O)OC / 20
CCOS(O)(=O)=O / 15
N#CNC#N / 1
OC(=O)C(F)(F)F / 4
OS(=O)(=O)C(F)(F)F / 4
CC(O)=O / 1
COS(O)(=O)=O / 8
Cl / 1
SC#N / 1
CC(O)=O / 1
N#CC(C#N)C#N / 1
CC(F)(F)S(O)(=N)=O / 1
C1C=CN=CC=1 / 1
CCOC(=O)C1=CC=CN=C1 / 3
CCN1C=CC(=CC=1)N2CCC(C)CC2 / 2
CN1C=CN(C)=C1 / 2
CN1C=CN(C)=C1C / 1
CCN1C=CN(C)C=1 / 3
CC(C)=CN1C=CN(C)=C1 / 1
CN1C=CN(CCC(F)(F)C(F)(F)F)=C1 / 3
I(c1ccccc1)c2ccccc2 / 1
CN(C)(C)C / 3
CCN(C)(C)C / 1
CCP(C)(C)C / 3
CN1(C)CCCC1 / 1
CCN1(C)CCCC1 / 2
CCN1C=CC=CC=1 / 2
CCN1C=CC(=CC=1)N(C)C / 2
CCN1C=CC=C(C)C=1 / 4

Training Set B

Name / Conform
C=C(C=N)N=N / 1
OC(=C)C=N / 1
CC(=N)C(S)=N / 1
SC(N=C)=NN=C / 1
O=N1ON=CC=1 / 1
NC(=N)C(=C)N=N / 1
NC(=N)N=N / 1
CC(C)(N)N=N / 1
NCC(N)=N / 1
NC(=N)CS / 1
OCC(O)=N / 1
CC(S)=NO / 1
NC(=S)C(S)=N / 1
CC(S)C(S)=N / 1
OCC(=N)C=C / 1
CSC(=N)C=C / 1
C=CN=NC=N / 1
N=CN(NC=S)C=N / 1
CS(=N)NC=C / 1
CC(=N)SC=S / 1
SC(=N)SC=C / 1
NC#N / 1
NCC(=C)C=N / 1
OCC(=C)C=N / 1
CN(N)C(=C)C=N / 1
COC(=C)C=N / 1
CSC(=C)C=N / 1
CC(O)C(=N)C=N / 1
SCC(=N)C=N / 1
CSC(=N)C=N / 1
OC(=N)N=C / 1
CC(=C)NC=N / 1
CN(C=N)C(=C)N=C / 1
CC(=N)OC=N / 1
NC(=N)OC=N / 1
OC(=N)OC=N / 1
N=CSSC=N / 1
CC(=C)C(O)=N / 1
CC(=N)C(=C)N=N / 1
CC(=N)C(N)=S / 1
CC(=N)C(C)=N / 1
CC(=N)C(O)=N / 1
CC(=N)NN / 1
CCC(O)=N / 1
CNC(=N)SS / 1
COC(S)=N / 1
CSC(O)=N / 1
OCN(C=N)C=O / 1
CC(=O)SC=N / 1
C=NNC(=O)C(=C)C=O / 1
NC(=O)C(=C)C=O / 1
SC(=N)C(=C)C=O / 1
NCC(=C)C=O / 1
CC(S)C(=C)C=O / 1
C=C(CS(=O)=O)C=O / 1
C=C(C=O)N1CNNCN1 / 1
COC(=C)C=O / 1
CSC(=C)C=O / 1
NS(=O)(=O)C(=C)C=O / 1
NNC(=O)C(=N)C=O / 1
NC(=O)C(=N)C=O / 1
NS(=O)(=O)C(=N)C=O / 1
CC(=N)CC=O / 1
N=C(CC=O)NC=O / 1
NS(=O)(=O)CC=O / 1
CC(=C)C(=O)N=C / 1
CC(=C)C(=O)N(N)C=O / 1
CC(=C)C(S)=O / 1
CC(=C)N(=O)=O / 1
CC(=C)N(O)C=O / 1
CC(=C)S(C)(=O)=O / 1
CC(=O)N=S=O / 1
CC(=N)C(=O)N=C / 1
CC(=N)CS(=O)=O / 1
CC(=N)N(C=O)N=C / 1
CC(=N)NS(=O)=O / 1
CC(=O)C(=C)S(=O)=O / 1
CC(N=C)C(C)=O / 1
CC(=O)C(C=O)N=N / 1
CC(=O)CN / 1
CC(=O)CO / 1
CCC(=N)N(C)C=O / 1
CCS(C)(=N)=O / 1
CN(C)N(=O)=O / 1
COC(=O)C(=N)NC=O / 1
SCC(=N)NC=O / 1
ON=CNC=O / 1
CC(NC=O)C(N)=S / 1
NC(=O)C(N)=S / 1
CC(=O)NS(=O)=O / 1
OC(=O)C(=O)C=C / 1
CC(=O)CS(=O)=O / 1
CS(=O)(=O)CS(=N)=O / 1
OC(=C)C(S)=O / 1
ONC(O)=O / 1
OC(=O)NS(=O)=O / 1
OS(=O)(=O)CS(=O)=O / 1
NC(=S)CS(=O)=O / 1
NC(=S)N=S=O / 1
SS(=O)(=O)CS(=O)=O / 1
SC(=N)C(=C)S(=O)=O / 1
NC(S)=NS(=O)=O / 1
O=S(=O)NNS(=O)=O / 1
CN(C)S(C)=O / 1
CN(C)S(O)(=O)=O / 1
CN(C=O)C(O)=C / 1
CNC(S)=O / 1
CN(C)C(=O)S(=O)=O / 1
CN(C=O)C(C)(O)C=O / 1
COC(=C)NC=O / 1
COC(=O)N=C / 1
COC(S)=O / 1
CONC=O / 1
CON(=O)=O / 1
COS(C)(=O)=O / 1
CS(=N)(=O)CS(=O)=O / 1
CSC(N)=O / 1
CS(=O)(=O)CS(=O)=O / 1
CN(N)S(C)(=O)=O / 1
CN(S(=O)=O)S(C)(=O)=O / 1
NS(=O)(=O)C=C / 1
C=CS(=O)(=O)N=C / 1
OC(=O)C=N / 1
CS(=O)(=O)N=S / 1
N=CNN(=O)=O / 1
C=NC(NC=O)N=C / 1
CN(C=O)C(C)(C)NC=O / 1
OC(=C)NC=O / 1
NC(=O)C(=C)N=C / 1
NNC(=O)N=C / 1
NC(=N)C(=O)N=C / 1
C=NN(C=O)N=N / 1
C=NOC(=O)NS(=O)=O / 1
OC(=O)ON=C / 1
NNC(=O)C(=C)N=N / 1
NC(=O)C(=C)N=N / 1
OC(=O)C(=C)N=N / 1
CC(=O)C(=C)N=N / 1
N=NC(=N)N(=O)=O / 1
CC(=O)C(N)=C / 1
O=S=NC(=O)NS(=O)=O / 1
NNC(=O)NS(=O)=O / 1
OC(=C)C(=O)NN=C / 1
NNC(=O)C(=N)NC=O / 1
NC(=N)CS(=O)=O / 1
NC(=N)NS(=O)=O / 1
CN(C)CC(=C)N(C)C=O / 1
CN(C)CC(=N)NC=O / 1
NNC(=S)NC=O / 1
NS(=O)(=O)CS(=O)=O / 1
CN(C=O)C(=O)C(=C)NC=O / 1
CC(=O)C(=C)NC=O / 1
C=C(CS(=O)=O)NC=O / 1
O=CNC(=S)N=S=O / 1
NC(=O)C(=N)NC=O / 1
CS(=O)(=O)ON=C / 1
C=CC(=O)N=C / 1
NC(=O)N=S / 1
C=CC(=N)C(=O)N=C / 1
NNC(=O)C(=N)C=C / 1
OC(=O)C(O)=O / 1
NC(C=C)=NC=O / 1
CN(C=O)C(=N)C=C / 1
C=CC(=N)OC=O / 1
OC(=O)C(=C)C(=O)C=C / 1
C=CC(=O)C(=C)C=N / 1
C=CC(=O)C(=C)N=N / 1
C=CC(=O)C(=C)N(=O)=O / 1
NC(=O)C(=O)C=C / 1
OC(=O)C(=N)C(=O)C=C / 1
C=CC(=O)C(=N)C=O / 1
C=CC(=O)C(C=O)C=O / 1
CC(S)C(=O)C=C / 1
NC(=O)NCC=C / 1
C=NN(C=S)C(=O)C=N / 1
CN(NC(N)=O)C=S / 1
O=S(=O)NNC=S / 1
CN(C=C)S(C)(=O)=O / 1
C=CNC(=O)NS(=O)=O / 1
SC(=O)NC=C / 1
C=CN(CC=O)C=O / 1
OC(=O)C(=C)OC=C / 1
CS(=O)(=O)OC=C / 1
CCS(=O)C=C / 1
OC(=O)CS(=O)(=O)C=C / 1
NN(C=C)C(N)=O / 1
NC(=O)NN(C=N)C=O / 1
NC(=O)NNS(=O)=O / 1
OC(=O)NOC(O)=O / 1
CSN(N=C)C(O)=O / 1
CS(=O)(=O)NC(N)=O / 1
NC(=O)NS(=O)(=O)N=S=O / 1
NC(=O)NS(N)(=O)=O / 1
OC(=O)NC(=S)N=S=O / 1
NC(=O)NC(=S)NC=O / 1
NC(=O)NC(=C)OC=C / 1
CN(C=S)C(=C)OC(N)=O / 1
NC(=O)ONC=O / 1
NC(=O)SC(O)=O / 1
CN(C=O)C(=N)SC(N)=O / 1
NNC(=O)C(=C)C(N)=O / 1
NC(=O)C(=C)C(S)=O / 1
CC(=N)C(=C)C(O)=O / 1
NC(=N)C(=C)C(O)=O / 1
CC(=O)C(=C)C(O)=O / 1
NC(=O)C(=C)N(=O)=O / 1
OC(=O)C(=C)OC=O / 1
COC(=C)C(N)=O / 1
OC(=O)C(=C)ON=C / 1
CS(=O)C(=C)C(N)=O / 1
NC(=O)C(=C)S(N)(=O)=O / 1
SC(=C)C(=O)C=N / 1
OCC(=O)C=N / 1
SCC(=O)C=N / 1
CC(=O)CC=N / 1
CS(=O)(=O)CC=N / 1
C=NN(=O)=O / 1
CC(=O)N(N)C=N / 1
CN(N(C=N)C=O)S(=O)=O / 1
CS(=O)(=O)NC=N / 1
CC(=C)N(C=N)C=O / 1
OC(=O)NC=N / 1
N=CN(C=O)C(NC=O)C=O / 1
NNC(=O)C(N)=O / 1
CN(O)C(=O)C(N)=O / 1
OC(=C)C(=N)C(O)=O / 1
NC(=S)C(=N)C(O)=O / 1
CC(=N)C(=N)C(N)=O / 1
NC(=N)C(=N)C(N)=O / 1
CC(=O)C(=N)C(O)=O / 1
NC(=O)C(=N)CC=O / 1
NN(C=O)C(=N)C(N)=O / 1
OC(=O)C(=O)C(S)=C / 1
NC(=O)C(=O)CC=O / 1
COC(=N)CC(O)=O / 1
OC(=O)C(S)C(=O)CS / 1
OC(=O)CN(C=N)C=O / 1
NC(=O)CS(N)(=O)=O / 1
NN(C=O)C(S)=N / 1
O=CNNC=O / 1
CN(C=O)S(N)(=O)=O / 1
O=CNC(=O)N=S=O / 1
OC(=O)NC=O / 1
C=C(OC=O)C=N / 1
CC(=C)OC=O / 1
C=COC=O / 1
CC(=N)OC=O / 1
NC(=N)OC=O / 1
OC(=N)OC=O / 1
N=CN(OC=O)C=O / 1
N=NN(OC=O)C=O / 1
N=C(NC=O)SC=O / 1
OC(=O)C(=C)C=N / 1
C=C(CS(=O)=O)C=N / 1
C=C(C=N)N(=O)=O / 1
CS(=O)(=O)C(=C)C=N / 1
OC(=O)C(=N)C=N / 1
OC(=C)C(=O)C=N / 1
NC(=S)CN=C / 1
NCC(N)=S / 1
NNC(N)=S / 1
CN(N)C(S)=S / 1
CC(O)C(N)=S / 1
NC(=S)CS / 1
O=CN=S / 1
N=CC(=S)NC=S / 1
CN(NC=S)C=S / 1
NC(=S)OC=C / 1
COC(N)=S / 1
COC(S)=S / 1
CSC(O)=S / 1
CCS(O)(=O)=O / 1
CC(=O)NC=S / 1
OC(=O)C(C#N)=N=C / 1
O=N=C(C#N)S(=O)=O / 1
CN(C(C)=O)C(N)=O / 1
NC(S)=S / 1
CC(O)=O / 1
NC=NC(N)=S / 1
C=N=C(C#N)C#N / 1
O=CN1C(C=Cc2ccccc12)C#N / 1
O=C1C=CNN1c2ccccc2 / 1
C=CC1=NN=NC1c2ccccc2 / 1
C3CN1C(C=Cc2ccccc12)=N3 / 1
O=C1C=C1c2ccccc2 / 1
O=C1OC=NC1c2ccccc2 / 1
C1C=CC=C1c2ccccc2 / 1
S=CCc2sc1ccccc1n2 / 1
OC(=O)C1=NNC(=C)C1c2sccc2 / 1
C=CC1C(=O)ON=C1c2ccccc2 / 1
SC1=NC=Cc2ncnn12 / 1
O=C(N1NCC=C1)c2ccccc2 / 1
c2cn1C=CN=Cc1c2 / 1
O=S(=O)c1cnc2SC=Cn12 / 1
O=CN1C(C(=O)NC1=S)c2ccccc2 / 1
S=C1NN=C(O1)c2sccc2 / 1
C=CS(=O)(=O)c2sc1ccccc1n2 / 1
O=C1OC=NN1c2ccccn2 / 1
OC(=O)NN=c1c(=O)nc2ccccc12 / 1
OC(=O)n1c(cc2ccccc12)C(O)=O / 1
O=C1NC(=S)Nc2ccnn12 / 1
O=C1NC=NC(=O)N1c2ccccc2 / 1
N=C1NC(=O)Nc2ccnn12 / 1
O=CCN1C(=O)Oc2ccccc12 / 1
O=C1NCN(O1)c2ccccc2 / 1
NC(=O)Sc2sc1ccccc1n2 / 1
OC(=O)C1=CC=NN(C1C=O)c2ccccc2 / 1
N=C(C#N)c2sc1ccccc1n2 / 1
SC(=N)C(C#N)c2nc1ccccc1n2 / 1
C=NOc1ncnc2nncc12 / 1
N=C(C#N)c2nc1ccccc1n2 / 1
N=C(c1ccccc1)c2ccccn2 / 1
N=C(c1ccccc1)C(=N)c2ccccc2 / 1
N=C1C(C(=O)c2ccccc12)N(=O)=O / 1
OC1CNN=C1c2ccccc2 / 1
N=C(Oc1ccccc1)c2ccccc2 / 1
C=C(n1ccnc1)C(=O)c2ccccc2 / 1
O=C(c1nccn1)c2ccccc2 / 1
O=C(c1sccc1)c2cnnc2 / 1
N=C1NN=C(N1)C(=O)c2sccc2 / 1
N=C(n1cncn1)C(=O)c2ccccc2 / 1
C=C1NN=C(S1)C(=O)c2sccc2 / 1
CC1(C)C(=C)N(C=O)c2ccccc12 / 1
C(c1ocnn1)c2ccccc2 / 1
O=CC1=NOCC1c2ccccc2 / 1
O=C1CC(=O)C(=O)C1c2ccccc2 / 1
O=C3Cn2c(=O)c1ccccc1c2=N3 / 1
s1ccc2c1N=Cn3cnnc23 / 1
S1SC(C=C1)=Nc2ccccc2 / 1
O=S1(=O)CCNC1=Nc2ccccc2 / 1
C=NN=c1c(=O)nc2ccccc12 / 1
CN3N=c1c(nc2ccccc12)=NC3=N / 1
CON=c1c(=O)nc2ccccc12 / 1
n1cc(cn1)N=Nc2ccccc2 / 1
S=C1N=CC=CN1c2ccccc2 / 1
n1nccc1Nc2ccccc2 / 1
N(c1ocnn1)c2ccccc2 / 1
N(c1scnn1)c2ccccc2 / 1
CC1=NNC(=S)N1c2ccccc2 / 1
N(Nc1ccccn1)c2ccccc2 / 1
On1nnc2ccccc12 / 1
N#CC3Sc2nc1ccccc1n2C=3 / 1
S=C3NN=c1c(nc2ccccc12)=N3 / 1
C=Nc1nnc2ccccc12 / 1
N=C1SSN=C1c2ccccc2 / 1
C=NC(C#N)(c1ccccc1)C(=N)c2ccccc2 / 1
C=C(Oc1ccccc1)c2ccccc2 / 1
S=C1SSC(=C1)c2ccccc2 / 1
C=C(c1ccccc1)S(=O)(=O)c2ccccc2 / 1
O=C(Nn1cnnc1)c2ccccc2 / 1
O=C1NS(=O)(=O)c2ccccc12 / 1
Nc2ccc1nccc1c2 / 1
O=C1NC(C=N1)c2ccccc2 / 1
NC1=NC=Nc2ccnn12 / 1
N=CNc2nc1ccccc1n2 / 1
C=C3Cn1c(cc2ccccc12)C3=O / 1
O=C1C(=O)c2nncnnc12 / 1
O=CC(C#N)c2nc1ccccc1n2 / 1
CC1=CC(=O)OC1c2ccccc2 / 1
CC1=CC(=O)NN1c2ccccc2 / 1
CN(C)C(=C)n1cnc2ccccc12 / 1
C1CN(N=N1)c2ccccc2 / 1
C1CON(C1)c2ccccc2 / 1
Cn1c(=S)nnc(=O)c2ccccc12 / 1
COn1nnc2ccccc12 / 1
CSc2nc1ccccc1n2 / 1
O=C(n1cccn1)c2ccnn2 / 1
OC(=O)c2cc1ccccc1n2C=O / 1
NC(=O)c2nc1ccccc1c2 / 1
C=CC1(C(=O)Nc2ccccc12)C(=C)C=O / 1
OC(=O)CC1=CSc2ncnn12 / 1