NPASS drugs

Drug Information

Drug ID:	NPD3816
Drug Name:	Berberine
Molecular Formula:	C20H18NO4
Canonical SMILES:	COc1c(OC)ccc2c1c[n+]1CCc3c(c1c2)cc1c(c3)OCO1
Standard InCHI:	InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
Standard InCHIKey:	YBHILYKTIRIUTE-UHFFFAOYSA-N
Max Developmental Stage:	Phase 1
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD3816

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	484
0.1-0.2	2121
0.2-0.3	9324
0.3-0.4	3761
0.4-0.5	9988
0.5-0.6	3308
0.6-0.7	1533
0.7-0.8	314
0.8-0.85	25
0.85-0.9	5
0.9-0.95	17
0.95-1	10

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	NPC202768
High Similarity	1.0	NPC53069
High Similarity	1.0	NPC296482
High Similarity	0.9789	NPC96405
High Similarity	0.9789	NPC171409
High Similarity	0.9734	NPC313189
High Similarity	0.9628	NPC36229
High Similarity	0.9628	NPC476581
High Similarity	0.9628	NPC16452
High Similarity	0.9526	NPC135549

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Drug Structure

NPD3816 OpenBabel08211704332D 25 29 0 0 0 0 0 0 0 0999 V2000 -7.0132 4.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 -7.0132 3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 O 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 17 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 21 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 23 1 0 0 0 0 M CHG 1 21 1 M END $$$$

External Identifiers

TTD	DNC000385; DNC000303
DrugBank	DB04115
ChEMBL	CHEMBL295124
IUPHAR/BPS
PharmaGKB	PA165860812
KEGG Drug	D00092
PubChem CID	2353
ChEBI	16118
CAS Number	2086-83-1

Drug Properties

Molecular Weight	336.12
ALogP	-1.583
MLogP	3.11
XLogP	2.896
HDA	0
HBD	0
Rotatable Bonds	4
TPSA	40.8
RO5 Violation	0