NPASS drugs

Drug Information

Drug ID:	NPD2666
Drug Name:	Amisulpride
Molecular Formula:	C17H27N3O4S
Canonical SMILES:	CCN1CCCC1CN=C(c1cc(c(cc1OC)N)S(=O)(=O)CC)O
Standard InCHI:	InChI=1S/C17H27N3O4S/c1-4-20-8-6-7-12(20)11-19-17(21)13-9-16(25(22,23)5-2)14(18)10-15(13)24-3/h9-10,12H,4-8,11,18H2,1-3H3,(H,19,21)
Standard InCHIKey:	NTJOBXMMWNYJFB-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD2666

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	258
0.1-0.2	2762
0.2-0.3	9995
0.3-0.4	4872
0.4-0.5	10868
0.5-0.6	2082
0.6-0.7	53
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similar Natural Products

High Similarity Level: Tc>=0.85; Intermediate Similarity Level: 0.7 <= Tc < 0.85; Remote Similarity Level: 0.65 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
Remote Similarity	0.6559	NPC219383
Remote Similarity	0.6471	NPC28510
Remote Similarity	0.6447	NPC473432
Remote Similarity	0.6422	NPC174629
Remote Similarity	0.6378	NPC310894
Remote Similarity	0.6359	NPC204970
Remote Similarity	0.635	NPC222592
Remote Similarity	0.635	NPC168486
Remote Similarity	0.6316	NPC70956
Remote Similarity	0.6316	NPC243834
Remote Similarity	0.6281	NPC168153
Remote Similarity	0.6276	NPC208280
Remote Similarity	0.6269	NPC249662
Remote Similarity	0.6262	NPC474059
Remote Similarity	0.6182	NPC469592
Remote Similarity	0.6182	NPC471080
Remote Similarity	0.6181	NPC225381
Remote Similarity	0.6175	NPC475910
Remote Similarity	0.6169	NPC9475
Remote Similarity	0.6166	NPC469428
Remote Similarity	0.6158	NPC322283
Remote Similarity	0.6154	NPC72291
Remote Similarity	0.615	NPC128237
Remote Similarity	0.615	NPC83790
Remote Similarity	0.615	NPC121772
Remote Similarity	0.6143	NPC469594
Remote Similarity	0.6142	NPC19555
Remote Similarity	0.6121	NPC232600
Remote Similarity	0.6108	NPC70092
Remote Similarity	0.6108	NPC283999
Remote Similarity	0.6093	NPC291535
Remote Similarity	0.6093	NPC475112
Remote Similarity	0.6093	NPC475085
Remote Similarity	0.6087	NPC329731
Remote Similarity	0.6075	NPC329747
Remote Similarity	0.6073	NPC168250
Remote Similarity	0.6073	NPC469589
Remote Similarity	0.6065	NPC473460
Remote Similarity	0.6058	NPC217294
Remote Similarity	0.6056	NPC477527
Remote Similarity	0.6055	NPC193777
Remote Similarity	0.6054	NPC152768
Remote Similarity	0.6054	NPC148183
Remote Similarity	0.6037	NPC473422
Remote Similarity	0.603	NPC315388
Remote Similarity	0.6029	NPC39822
Remote Similarity	0.6026	NPC153467
Remote Similarity	0.6019	NPC84478
Remote Similarity	0.601	NPC70172
Remote Similarity	0.6009	NPC476106
Remote Similarity	0.6	NPC288430
Remote Similarity	0.6	NPC303658
Remote Similarity	0.6	NPC324702
Remote Similarity	0.599	NPC473007
Remote Similarity	0.5981	NPC72211
Remote Similarity	0.5981	NPC477186
Remote Similarity	0.5969	NPC291359
Remote Similarity	0.5964	NPC478074
Remote Similarity	0.5962	NPC13880
Remote Similarity	0.5962	NPC303214
Remote Similarity	0.5959	NPC184161
Remote Similarity	0.5952	NPC473008
Remote Similarity	0.5949	NPC10875
Remote Similarity	0.5949	NPC10730
Remote Similarity	0.5947	NPC128115
Remote Similarity	0.5946	NPC166667
Remote Similarity	0.5942	NPC62069
Remote Similarity	0.594	NPC470889
Remote Similarity	0.5936	NPC472111
Remote Similarity	0.5933	NPC4910
Remote Similarity	0.5933	NPC469830
Remote Similarity	0.5931	NPC228040
Remote Similarity	0.5931	NPC473185
Remote Similarity	0.5931	NPC283152
Remote Similarity	0.593	NPC204179
Remote Similarity	0.593	NPC254700
Remote Similarity	0.5924	NPC22476
Remote Similarity	0.5921	NPC310118
Remote Similarity	0.5917	NPC226914
Remote Similarity	0.5915	NPC59827
Remote Similarity	0.5915	NPC131017
Remote Similarity	0.5915	NPC184933
Remote Similarity	0.5909	NPC230942
Remote Similarity	0.5909	NPC86966
Remote Similarity	0.5909	NPC191863
Remote Similarity	0.5909	NPC315498
Remote Similarity	0.5909	NPC133470
Remote Similarity	0.5909	NPC289776
Remote Similarity	0.5901	NPC11464
Remote Similarity	0.5897	NPC203424
Remote Similarity	0.5897	NPC206372
Remote Similarity	0.5894	NPC98197
Remote Similarity	0.589	NPC87714
Remote Similarity	0.5888	NPC108847
Remote Similarity	0.5888	NPC70259
Remote Similarity	0.5886	NPC43275
Remote Similarity	0.588	NPC18487
Remote Similarity	0.5869	NPC203972
Remote Similarity	0.5867	NPC326349
Remote Similarity	0.5867	NPC323336
Remote Similarity	0.5862	NPC110151
Remote Similarity	0.586	NPC472191
Remote Similarity	0.586	NPC272706
Remote Similarity	0.5859	NPC235628
Remote Similarity	0.5859	NPC306366
Remote Similarity	0.5857	NPC74382
Remote Similarity	0.5857	NPC206251
Remote Similarity	0.5854	NPC127082
Remote Similarity	0.5852	NPC17388
Remote Similarity	0.5852	NPC53596
Remote Similarity	0.5852	NPC112823
Remote Similarity	0.5852	NPC160120
Remote Similarity	0.5852	NPC477532
Remote Similarity	0.5852	NPC471308
Remote Similarity	0.5852	NPC289330
Remote Similarity	0.5851	NPC83289
Remote Similarity	0.5851	NPC477838
Remote Similarity	0.5851	NPC212850
Remote Similarity	0.5851	NPC477837
Remote Similarity	0.5851	NPC189724
Remote Similarity	0.585	NPC94292
Remote Similarity	0.5849	NPC475411
Remote Similarity	0.5849	NPC203628
Remote Similarity	0.5848	NPC48353
Remote Similarity	0.5848	NPC316981
Remote Similarity	0.5845	NPC162484
Remote Similarity	0.5845	NPC260118
Remote Similarity	0.5841	NPC205934
Remote Similarity	0.5841	NPC43787
Remote Similarity	0.5837	NPC94943
Remote Similarity	0.5837	NPC194740
Remote Similarity	0.5833	NPC108826
Remote Similarity	0.5833	NPC474649
Remote Similarity	0.5833	NPC473179
Remote Similarity	0.5833	NPC213530
Remote Similarity	0.5833	NPC474652
Remote Similarity	0.5833	NPC193267
Remote Similarity	0.583	NPC269449
Remote Similarity	0.583	NPC476651
Remote Similarity	0.5829	NPC177404
Remote Similarity	0.5826	NPC232727
Remote Similarity	0.5818	NPC257511
Remote Similarity	0.5817	NPC215747
Remote Similarity	0.5817	NPC192939
Remote Similarity	0.5815	NPC274732
Remote Similarity	0.5815	NPC305984
Remote Similarity	0.5814	NPC194967
Remote Similarity	0.5813	NPC85482
Remote Similarity	0.5812	NPC470824
Remote Similarity	0.5811	NPC470931
Remote Similarity	0.5811	NPC205926
Remote Similarity	0.5808	NPC29647
Remote Similarity	0.5808	NPC174760
Remote Similarity	0.5808	NPC37205
Remote Similarity	0.5808	NPC160931
Remote Similarity	0.5799	NPC311357
Remote Similarity	0.5799	NPC295898
Remote Similarity	0.5797	NPC265383
Remote Similarity	0.5796	NPC66191
Remote Similarity	0.5796	NPC316297
Remote Similarity	0.5796	NPC314817
Remote Similarity	0.5794	NPC307963
Remote Similarity	0.5789	NPC190007
Remote Similarity	0.5787	NPC315257
Remote Similarity	0.5784	NPC184437
Remote Similarity	0.5784	NPC130921
Remote Similarity	0.5782	NPC180253
Remote Similarity	0.5782	NPC219170
Remote Similarity	0.5781	NPC9373
Remote Similarity	0.578	NPC329793
Remote Similarity	0.578	NPC315957
Remote Similarity	0.5779	NPC79328
Remote Similarity	0.5778	NPC119722
Remote Similarity	0.5778	NPC325013
Remote Similarity	0.5775	NPC477526
Remote Similarity	0.5773	NPC223427
Remote Similarity	0.5769	NPC28368
Remote Similarity	0.5767	NPC314113
Remote Similarity	0.5767	NPC230313
Remote Similarity	0.5767	NPC29472
Remote Similarity	0.5767	NPC243626
Remote Similarity	0.5764	NPC257354
Remote Similarity	0.5763	NPC41801
Remote Similarity	0.5762	NPC28425
Remote Similarity	0.5762	NPC276060
Remote Similarity	0.576	NPC100863
Remote Similarity	0.5755	NPC224293
Remote Similarity	0.5754	NPC471314
Remote Similarity	0.5754	NPC471315
Remote Similarity	0.5753	NPC472330
Remote Similarity	0.5753	NPC472329
Remote Similarity	0.5752	NPC471741
Remote Similarity	0.5751	NPC245974
Remote Similarity	0.5749	NPC72980
Remote Similarity	0.5747	NPC285558
Remote Similarity	0.5747	NPC14339
Remote Similarity	0.5742	NPC212535
Remote Similarity	0.5742	NPC176127
Remote Similarity	0.5742	NPC311936
Remote Similarity	0.5741	NPC251090

Drug Structure

NPD2666 OpenBabel08211702172D 28 29 0 0 1 0 0 0 0 0999 V2000 -5.9673 4.9479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2242 4.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6551 4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2731 4.5878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 24 1 0 0 0 0 4 20 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 12 1 0 0 0 0 8 20 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 15 2 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 19 2 3 0 0 0 17 21 1 0 0 0 0 18 26 1 0 0 0 0 18 27 1 0 0 0 0 21 28 1 0 0 0 0 22 25 2 0 0 0 0 23 25 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000848
DrugBank	DB06288
ChEMBL	CHEMBL243712
IUPHAR/BPS	963
PharmaGKB	PA162565877
KEGG Drug	D07310
PubChem CID	2159
ChEBI	64045
CAS Number	71675-85-9

Drug Properties

Molecular Weight	369.17
ALogP	-1.4173
MLogP	2.45
XLogP	1.948
HDA	6
HBD	2
Rotatable Bonds	12
TPSA	113.6
RO5 Violation	0