NPASS drugs

Drug Information

Drug ID:	NPD3815
Drug Name:	Berberine Chloride
Molecular Formula:	C20H18NO4.ClH
Canonical SMILES:	COc1c(OC)ccc2c1c[n+]1CCc3c(c1c2)cc1c(c3)OCO1.[Cl-]
Standard InCHI:	"InChI=1S/C20H18NO4.ClH/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;1H/q+1;/p-1"
Standard InCHIKey:	VKJGBAJNNALVAV-UHFFFAOYSA-M
Max Developmental Stage:	Phase 1
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD3815

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	150467
0.1-0.2	58191
0.2-0.3	2986
0.3-0.4	42
0.4-0.5	12
0.5-0.6	14
0.6-0.7	9
0.7-0.8	5
0.8-0.85	6
0.85-0.9	2
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	NPC296482
High Similarity	1.0	NPC611862
High Similarity	0.9825	NPC53069
High Similarity	0.9825	NPC611868
High Similarity	0.8833	NPC96405
High Similarity	0.8667	NPC171409
Intermediate Similarity	0.8475	NPC36229
Intermediate Similarity	0.8387	NPC202768
Intermediate Similarity	0.8387	NPC605793
Intermediate Similarity	0.8305	NPC16452
Intermediate Similarity	0.8305	NPC164203
Intermediate Similarity	0.8305	NPC603777
Intermediate Similarity	0.7656	NPC183485
Intermediate Similarity	0.7576	NPC476581
Intermediate Similarity	0.7188	NPC313189
Intermediate Similarity	0.7164	NPC545129
Intermediate Similarity	0.7101	NPC268334
Remote Similarity	0.697	NPC202605
Remote Similarity	0.697	NPC607727
Remote Similarity	0.6765	NPC568607
Remote Similarity	0.6716	NPC602626
Remote Similarity	0.6667	NPC122225
Remote Similarity	0.6667	NPC269699
Remote Similarity	0.6615	NPC135549
Remote Similarity	0.6615	NPC521096
Remote Similarity	0.6232	NPC503738
Remote Similarity	0.5915	NPC158494
Remote Similarity	0.5915	NPC544828
Remote Similarity	0.5909	NPC544027
Remote Similarity	0.5909	NPC607600
Remote Similarity	0.589	NPC481435
Remote Similarity	0.5775	NPC504504
Remote Similarity	0.5758	NPC4071
Remote Similarity	0.5584	NPC476579
Remote Similarity	0.5571	NPC31930
Remote Similarity	0.5571	NPC604627
Remote Similarity	0.5405	NPC521343
Remote Similarity	0.5342	NPC112206
Remote Similarity	0.5342	NPC476582
Remote Similarity	0.52	NPC594405

Drug Structure

NPD3815 OpenBabel08211704332D 26 29 0 0 0 0 0 0 0 0999 V2000 1.3660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9670 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -5.0000 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 1.3660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3793 -6.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3793 -4.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 3.1709 0.0000 Cl 0 5 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 2 21 1 26 -1 M END $$$$

External Identifiers

TTD
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	0
ChEBI
CAS Number

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