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

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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

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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