NPASS drugs

Drug Information

Drug ID:	NPD2569
Drug Name:	Cocaine
Molecular Formula:	C17H21NO4
Canonical SMILES:	COC(=O)[C@H]1[C@H](C[C@H]2N([C@@H]1CC2)C)OC(=O)c1ccccc1
Standard InCHI:	InChI=1S/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15+/m0/s1
Standard InCHIKey:	ZPUCINDJVBIVPJ-LJISPDSOSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD2569

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	114
0.1-0.2	653
0.2-0.3	1997
0.3-0.4	5780
0.4-0.5	9235
0.5-0.6	11356
0.6-0.7	1680
0.7-0.8	68
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	1

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
High Similarity	1.0	NPC281104
High Similarity	0.8906	NPC26285
Intermediate Similarity	0.8195	NPC291027
Intermediate Similarity	0.8195	NPC317474
Intermediate Similarity	0.8195	NPC213126
Intermediate Similarity	0.8195	NPC84281
Intermediate Similarity	0.8195	NPC169485
Intermediate Similarity	0.7914	NPC69496
Intermediate Similarity	0.7908	NPC476443
Intermediate Similarity	0.7908	NPC133817
Intermediate Similarity	0.7826	NPC65310
Intermediate Similarity	0.781	NPC285394
Intermediate Similarity	0.7746	NPC233910
Intermediate Similarity	0.7746	NPC245836
Intermediate Similarity	0.7582	NPC68967
Intermediate Similarity	0.7566	NPC214239
Intermediate Similarity	0.75	NPC474847
Intermediate Similarity	0.7407	NPC149691
Intermediate Similarity	0.7405	NPC469636
Intermediate Similarity	0.7388	NPC307651
Intermediate Similarity	0.7349	NPC35680
Intermediate Similarity	0.7313	NPC474176
Intermediate Similarity	0.7313	NPC128368
Intermediate Similarity	0.7287	NPC474365
Intermediate Similarity	0.7287	NPC301943
Intermediate Similarity	0.7273	NPC265407
Intermediate Similarity	0.7273	NPC83628
Intermediate Similarity	0.7218	NPC158854
Intermediate Similarity	0.7214	NPC50872
Intermediate Similarity	0.7205	NPC26353
Intermediate Similarity	0.7188	NPC146351
Intermediate Similarity	0.7164	NPC474157
Intermediate Similarity	0.7152	NPC161827
Intermediate Similarity	0.7143	NPC474364
Intermediate Similarity	0.7133	NPC319645
Intermediate Similarity	0.7124	NPC297322
Intermediate Similarity	0.7111	NPC82899
Intermediate Similarity	0.7111	NPC270699
Intermediate Similarity	0.711	NPC166979
Intermediate Similarity	0.7109	NPC35448
Intermediate Similarity	0.7109	NPC78701
Intermediate Similarity	0.7109	NPC225060
Intermediate Similarity	0.7103	NPC103605
Intermediate Similarity	0.7103	NPC81092
Intermediate Similarity	0.709	NPC196246
Intermediate Similarity	0.709	NPC214067
Intermediate Similarity	0.708	NPC210092
Intermediate Similarity	0.7073	NPC35345
Intermediate Similarity	0.7055	NPC52059
Intermediate Similarity	0.7055	NPC470069
Intermediate Similarity	0.7054	NPC325497
Intermediate Similarity	0.7052	NPC162694
Intermediate Similarity	0.7045	NPC167336
Intermediate Similarity	0.7045	NPC269457
Intermediate Similarity	0.7037	NPC210089
Intermediate Similarity	0.7037	NPC476750
Intermediate Similarity	0.7037	NPC1082
Intermediate Similarity	0.7037	NPC305912
Intermediate Similarity	0.7034	NPC305717
Intermediate Similarity	0.7031	NPC276775
Intermediate Similarity	0.7031	NPC92754
Intermediate Similarity	0.7031	NPC249912
Intermediate Similarity	0.703	NPC474858
Intermediate Similarity	0.7021	NPC473243
Intermediate Similarity	0.7019	NPC148468
Intermediate Similarity	0.7019	NPC263709
Intermediate Similarity	0.7019	NPC310403
Intermediate Similarity	0.7019	NPC97380
Intermediate Similarity	0.7019	NPC63210
Intermediate Similarity	0.7019	NPC243673
Intermediate Similarity	0.7015	NPC10251
Intermediate Similarity	0.7015	NPC17417
Intermediate Similarity	0.7011	NPC141440
Intermediate Similarity	0.7007	NPC474363
Intermediate Similarity	0.7	NPC42211
Remote Similarity	0.6993	NPC472703
Remote Similarity	0.6985	NPC269340
Remote Similarity	0.6978	NPC190298
Remote Similarity	0.6966	NPC476599
Remote Similarity	0.6963	NPC251854
Remote Similarity	0.6963	NPC93084
Remote Similarity	0.6944	NPC472704
Remote Similarity	0.694	NPC56493
Remote Similarity	0.6934	NPC161611
Remote Similarity	0.6933	NPC90194
Remote Similarity	0.6933	NPC475598
Remote Similarity	0.6933	NPC49577
Remote Similarity	0.6933	NPC9687
Remote Similarity	0.6933	NPC79465
Remote Similarity	0.6933	NPC151706
Remote Similarity	0.6933	NPC475318
Remote Similarity	0.6933	NPC476102
Remote Similarity	0.6933	NPC474787
Remote Similarity	0.6933	NPC474855
Remote Similarity	0.6933	NPC260045
Remote Similarity	0.6933	NPC474811
Remote Similarity	0.6933	NPC273907
Remote Similarity	0.6933	NPC293377
Remote Similarity	0.6933	NPC118099
Remote Similarity	0.6933	NPC76785
Remote Similarity	0.6923	NPC118343
Remote Similarity	0.6923	NPC329992
Remote Similarity	0.6918	NPC472706
Remote Similarity	0.6913	NPC313663
Remote Similarity	0.6912	NPC476003
Remote Similarity	0.6901	NPC80150
Remote Similarity	0.6894	NPC234305
Remote Similarity	0.6894	NPC89886
Remote Similarity	0.6892	NPC147561
Remote Similarity	0.6884	NPC153053
Remote Similarity	0.6884	NPC308744
Remote Similarity	0.6879	NPC128683
Remote Similarity	0.6875	NPC223351
Remote Similarity	0.6875	NPC130398
Remote Similarity	0.6871	NPC474058
Remote Similarity	0.6871	NPC472707
Remote Similarity	0.6871	NPC213969
Remote Similarity	0.6871	NPC165726
Remote Similarity	0.687	NPC70624
Remote Similarity	0.6866	NPC37622
Remote Similarity	0.6866	NPC119271
Remote Similarity	0.6866	NPC30594
Remote Similarity	0.686	NPC27887
Remote Similarity	0.6852	NPC211525
Remote Similarity	0.6852	NPC153694
Remote Similarity	0.6845	NPC293255
Remote Similarity	0.6845	NPC21752
Remote Similarity	0.6845	NPC298851
Remote Similarity	0.6845	NPC476425
Remote Similarity	0.6845	NPC210415
Remote Similarity	0.6845	NPC181138
Remote Similarity	0.6845	NPC276993
Remote Similarity	0.6838	NPC292758
Remote Similarity	0.6838	NPC174099
Remote Similarity	0.6838	NPC65855
Remote Similarity	0.6833	NPC124302
Remote Similarity	0.6833	NPC70290
Remote Similarity	0.6833	NPC73020
Remote Similarity	0.6833	NPC14622
Remote Similarity	0.6833	NPC46744
Remote Similarity	0.6833	NPC215098
Remote Similarity	0.6826	NPC476749
Remote Similarity	0.6821	NPC153617
Remote Similarity	0.6818	NPC477904
Remote Similarity	0.6818	NPC183270
Remote Similarity	0.6816	NPC33256
Remote Similarity	0.6812	NPC272524
Remote Similarity	0.6809	NPC469574
Remote Similarity	0.6806	NPC160493
Remote Similarity	0.6802	NPC309692
Remote Similarity	0.6798	NPC166521
Remote Similarity	0.6798	NPC94499
Remote Similarity	0.6798	NPC172769
Remote Similarity	0.6798	NPC184195
Remote Similarity	0.6798	NPC205
Remote Similarity	0.6798	NPC124690
Remote Similarity	0.6798	NPC281470
Remote Similarity	0.6797	NPC216149
Remote Similarity	0.6797	NPC208170
Remote Similarity	0.6794	NPC203925
Remote Similarity	0.6792	NPC162104
Remote Similarity	0.6791	NPC209632
Remote Similarity	0.6788	NPC167504
Remote Similarity	0.678	NPC40539
Remote Similarity	0.6779	NPC475508
Remote Similarity	0.6776	NPC2173
Remote Similarity	0.6776	NPC202771
Remote Similarity	0.6776	NPC119818
Remote Similarity	0.6776	NPC328700
Remote Similarity	0.6772	NPC476444
Remote Similarity	0.6765	NPC40178
Remote Similarity	0.6759	NPC474283
Remote Similarity	0.6759	NPC475692
Remote Similarity	0.6758	NPC226652
Remote Similarity	0.6758	NPC72788
Remote Similarity	0.6758	NPC314100
Remote Similarity	0.6758	NPC120671
Remote Similarity	0.6742	NPC108276
Remote Similarity	0.6742	NPC163578
Remote Similarity	0.6742	NPC226708
Remote Similarity	0.6739	NPC321852
Remote Similarity	0.6739	NPC474314
Remote Similarity	0.6739	NPC158282
Remote Similarity	0.6739	NPC79496
Remote Similarity	0.6735	NPC275576
Remote Similarity	0.6735	NPC476033
Remote Similarity	0.6733	NPC470278
Remote Similarity	0.6724	NPC473562
Remote Similarity	0.6722	NPC477258
Remote Similarity	0.6716	NPC114594
Remote Similarity	0.6716	NPC31786
Remote Similarity	0.6715	NPC24777
Remote Similarity	0.6714	NPC474095
Remote Similarity	0.6714	NPC474685
Remote Similarity	0.6712	NPC475691
Remote Similarity	0.6711	NPC134937
Remote Similarity	0.6711	NPC473359
Remote Similarity	0.6711	NPC298547
Remote Similarity	0.6711	NPC324898
Remote Similarity	0.6711	NPC474608

Drug Structure

NPD2569 OpenBabel08211702172D 22 24 0 0 1 0 0 0 0 0999 V2000 0.4352 -0.7511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3020 2.5812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9394 1.0677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1094 1.5469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9394 0.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2794 1.0677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1094 -0.3700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5729 -2.0759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1363 -1.3005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0151 -1.3971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2794 0.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3845 -2.1188 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8814 -0.3765 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8440 -0.4541 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4494 -0.3700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0431 0.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -1.0328 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4494 -1.3284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9805 1.1566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5982 1.6697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6194 0.1092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 10 12 1 0 0 0 0 10 14 1 0 0 0 0 11 16 1 0 0 0 0 12 8 1 6 0 0 0 12 18 1 0 0 0 0 13 9 1 6 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 1 0 0 0 15 17 1 1 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000834
DrugBank	DB00907
ChEMBL	CHEMBL370805
IUPHAR/BPS	2286
PharmaGKB	PA449072
KEGG Drug	D00110
PubChem CID	446220
ChEBI	27958
CAS Number	50-36-2

Drug Properties

Molecular Weight	303.15
ALogP	-1.1243
MLogP	2.78
XLogP	3.336
HDA	5
HBD	0
Rotatable Bonds	7
TPSA	55.84
RO5 Violation	0