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 3
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD3816

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	151072
0.1-0.2	57460
0.2-0.3	3107
0.3-0.4	47
0.4-0.5	10
0.5-0.6	14
0.6-0.7	9
0.7-0.8	7
0.8-0.85	4
0.85-0.9	4
0.9-0.95	0
0.95-1	4

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	NPC53069
High Similarity	1.0	NPC611868
High Similarity	0.9825	NPC296482
High Similarity	0.9825	NPC611862
High Similarity	0.8814	NPC171409
High Similarity	0.8667	NPC96405
High Similarity	0.8525	NPC202768
High Similarity	0.8525	NPC605793
Intermediate Similarity	0.8448	NPC16452
Intermediate Similarity	0.8448	NPC164203
Intermediate Similarity	0.8448	NPC603777
Intermediate Similarity	0.8305	NPC36229
Intermediate Similarity	0.7778	NPC183485
Intermediate Similarity	0.7424	NPC476581
Intermediate Similarity	0.7273	NPC545129
Intermediate Similarity	0.7206	NPC268334
Intermediate Similarity	0.7077	NPC202605
Intermediate Similarity	0.7077	NPC607727
Intermediate Similarity	0.7031	NPC313189
Remote Similarity	0.6866	NPC568607
Remote Similarity	0.6818	NPC602626
Remote Similarity	0.6765	NPC122225
Remote Similarity	0.6765	NPC269699
Remote Similarity	0.6719	NPC135549
Remote Similarity	0.6719	NPC521096
Remote Similarity	0.6324	NPC503738
Remote Similarity	0.6	NPC158494
Remote Similarity	0.6	NPC544828
Remote Similarity	0.5857	NPC504504
Remote Similarity	0.5846	NPC4071
Remote Similarity	0.5758	NPC544027
Remote Similarity	0.5758	NPC607600
Remote Similarity	0.5753	NPC481435
Remote Similarity	0.5652	NPC31930
Remote Similarity	0.5652	NPC604627
Remote Similarity	0.5479	NPC521343
Remote Similarity	0.5455	NPC476579
Remote Similarity	0.5417	NPC112206
Remote Similarity	0.527	NPC594405
Remote Similarity	0.5205	NPC476582
Remote Similarity	0.5068	NPC610780
Remote Similarity	0.5063	NPC31860

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