NPASS drugs

Drug Information

Drug ID:	NPD3444
Drug Name:	Doxepin
Molecular Formula:	C19H21NO
Canonical SMILES:	CN(CCC=C1c2ccccc2OCc2c1cccc2)C
Standard InCHI:	InChI=1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3
Standard InCHIKey:	ODQWQRRAPPTVAG-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD3444

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	142
0.1-0.2	1176
0.2-0.3	2942
0.3-0.4	9820
0.4-0.5	3257
0.5-0.6	7791
0.6-0.7	5254
0.7-0.8	502
0.8-0.85	6
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

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Similarity Level	Similarity Score	Natural Product ID
Intermediate Similarity	0.8333	NPC326801
Intermediate Similarity	0.816	NPC255253
Intermediate Similarity	0.813	NPC321133
Intermediate Similarity	0.8045	NPC318591
Intermediate Similarity	0.8045	NPC231163
Intermediate Similarity	0.8016	NPC328267
Intermediate Similarity	0.792	NPC212559
Intermediate Similarity	0.7876	NPC95755
Intermediate Similarity	0.7869	NPC283169
Intermediate Similarity	0.7845	NPC241224

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Drug Structure

NPD3444 OpenBabel08211703112D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.0017 -5.0399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1764 -6.3096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 -2.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9944 -1.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4644 -3.6796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -2.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1974 -2.9994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6869 -4.6545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0461 -5.3347 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 10 18 2 0 0 0 0 11 17 2 3 0 0 0 12 19 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000177
DrugBank	DB01142
ChEMBL	CHEMBL101740
IUPHAR/BPS
PharmaGKB	PA449409
KEGG Drug	D07875
PubChem CID
ChEBI	36691
CAS Number	1668-19-5

Drug Properties

Molecular Weight	279.16
ALogP	0.0711
MLogP	3.33
XLogP	5.105
HDA	1
HBD	0
Rotatable Bonds	5
TPSA	12.47
RO5 Violation	1