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:	Phase 4
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD2569

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	98319
0.1-0.2	107443
0.2-0.3	5512
0.3-0.4	405
0.4-0.5	48
0.5-0.6	1
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similar Natural Products

High Similarity: Tc>=0.85; Intermediate Similarity: 0.7 <= Tc < 0.85; Remote Similarity: 0.5 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	1.0	NPC508378
High Similarity	1.0	NPC599862
Remote Similarity	0.6364	NPC597508
Remote Similarity	0.625	NPC26285
Remote Similarity	0.625	NPC551766
Remote Similarity	0.625	NPC570472
Remote Similarity	0.625	NPC609506
Remote Similarity	0.614	NPC513958
Remote Similarity	0.614	NPC596943
Remote Similarity	0.5167	NPC253096

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