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 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

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
High Similarity	0.9468	NPC31930
High Similarity	0.9415	NPC477019
High Similarity	0.9362	NPC476582
High Similarity	0.9362	NPC4071
High Similarity	0.9362	NPC476578
High Similarity	0.9282	NPC112206
High Similarity	0.9282	NPC202605
High Similarity	0.9242	NPC100079
High Similarity	0.9242	NPC23614
High Similarity	0.9211	NPC234197
High Similarity	0.91	NPC46451
High Similarity	0.9091	NPC235076
High Similarity	0.9086	NPC251160
High Similarity	0.9043	NPC195268
High Similarity	0.9043	NPC133140
High Similarity	0.904	NPC271215
High Similarity	0.904	NPC149471
High Similarity	0.8889	NPC188420
High Similarity	0.8794	NPC290689
High Similarity	0.878	NPC118121
High Similarity	0.8585	NPC204446
High Similarity	0.8579	NPC204385
Intermediate Similarity	0.8368	NPC206201
Intermediate Similarity	0.8326	NPC22481
Intermediate Similarity	0.8325	NPC174049
Intermediate Similarity	0.8318	NPC201508
Intermediate Similarity	0.8317	NPC473822
Intermediate Similarity	0.8271	NPC278525
Intermediate Similarity	0.8249	NPC108342
Intermediate Similarity	0.8213	NPC236668
Intermediate Similarity	0.8211	NPC182907
Intermediate Similarity	0.8211	NPC189903
Intermediate Similarity	0.8203	NPC253675
Intermediate Similarity	0.82	NPC287437
Intermediate Similarity	0.8174	NPC166722
Intermediate Similarity	0.8173	NPC146976
Intermediate Similarity	0.816	NPC122463
Intermediate Similarity	0.8157	NPC255800
Intermediate Similarity	0.8157	NPC96584
Intermediate Similarity	0.8105	NPC312872
Intermediate Similarity	0.8082	NPC295228
Intermediate Similarity	0.8049	NPC470164
Intermediate Similarity	0.8049	NPC323345
Intermediate Similarity	0.8038	NPC266931
Intermediate Similarity	0.8018	NPC210296
Intermediate Similarity	0.8009	NPC473513
Intermediate Similarity	0.8	NPC285558
Intermediate Similarity	0.7991	NPC124313
Intermediate Similarity	0.7991	NPC210434
Intermediate Similarity	0.7982	NPC207283
Intermediate Similarity	0.7982	NPC84164
Intermediate Similarity	0.7963	NPC214980
Intermediate Similarity	0.7952	NPC162530
Intermediate Similarity	0.7936	NPC24019
Intermediate Similarity	0.7907	NPC280272
Intermediate Similarity	0.79	NPC476999
Intermediate Similarity	0.7895	NPC167860
Intermediate Similarity	0.7895	NPC123976
Intermediate Similarity	0.789	NPC476997
Intermediate Similarity	0.7887	NPC173080
Intermediate Similarity	0.7854	NPC476998
Intermediate Similarity	0.7854	NPC476996
Intermediate Similarity	0.7833	NPC224928
Intermediate Similarity	0.782	NPC316981
Intermediate Similarity	0.7817	NPC183537
Intermediate Similarity	0.7817	NPC179704
Intermediate Similarity	0.781	NPC470020
Intermediate Similarity	0.7808	NPC476994
Intermediate Similarity	0.7789	NPC24954
Intermediate Similarity	0.7773	NPC208284
Intermediate Similarity	0.7767	NPC148409
Intermediate Similarity	0.7767	NPC213530
Intermediate Similarity	0.7767	NPC193267
Intermediate Similarity	0.7762	NPC174672
Intermediate Similarity	0.7762	NPC174758
Intermediate Similarity	0.7739	NPC77878
Intermediate Similarity	0.7729	NPC270515
Intermediate Similarity	0.7723	NPC114335
Intermediate Similarity	0.7723	NPC280964
Intermediate Similarity	0.7723	NPC141915
Intermediate Similarity	0.7718	NPC11017
Intermediate Similarity	0.7714	NPC82548
Intermediate Similarity	0.7713	NPC90875
Intermediate Similarity	0.7706	NPC322482
Intermediate Similarity	0.7703	NPC472111
Intermediate Similarity	0.7703	NPC233334
Intermediate Similarity	0.7699	NPC99891
Intermediate Similarity	0.7692	NPC469792
Intermediate Similarity	0.7692	NPC475774
Intermediate Similarity	0.7688	NPC249405
Intermediate Similarity	0.7681	NPC232727
Intermediate Similarity	0.7678	NPC469589
Intermediate Similarity	0.7673	NPC92111
Intermediate Similarity	0.7665	NPC287588
Intermediate Similarity	0.7656	NPC47059
Intermediate Similarity	0.7656	NPC264166
Intermediate Similarity	0.7656	NPC274291
Intermediate Similarity	0.7656	NPC329708
Intermediate Similarity	0.7656	NPC118832
Intermediate Similarity	0.7656	NPC165349
Intermediate Similarity	0.7644	NPC476995
Intermediate Similarity	0.7638	NPC284559
Intermediate Similarity	0.7633	NPC176538
Intermediate Similarity	0.763	NPC470931
Intermediate Similarity	0.7628	NPC170114
Intermediate Similarity	0.7624	NPC312531
Intermediate Similarity	0.7624	NPC76748
Intermediate Similarity	0.7621	NPC119134
Intermediate Similarity	0.7619	NPC41178
Intermediate Similarity	0.7619	NPC216459
Intermediate Similarity	0.7619	NPC138487
Intermediate Similarity	0.7598	NPC307963
Intermediate Similarity	0.7583	NPC474595
Intermediate Similarity	0.7581	NPC470549
Intermediate Similarity	0.7579	NPC146288
Intermediate Similarity	0.7574	NPC296527
Intermediate Similarity	0.7568	NPC246381
Intermediate Similarity	0.756	NPC199277
Intermediate Similarity	0.756	NPC135887
Intermediate Similarity	0.7559	NPC11464
Intermediate Similarity	0.7546	NPC274982
Intermediate Similarity	0.7544	NPC217554
Intermediate Similarity	0.7535	NPC474594
Intermediate Similarity	0.7526	NPC26850
Intermediate Similarity	0.7526	NPC93593
Intermediate Similarity	0.7524	NPC251090
Intermediate Similarity	0.7524	NPC13880
Intermediate Similarity	0.7522	NPC284141
Intermediate Similarity	0.7512	NPC302001
Intermediate Similarity	0.7512	NPC329541
Intermediate Similarity	0.75	NPC177404
Intermediate Similarity	0.7489	NPC314954
Intermediate Similarity	0.7489	NPC473183
Intermediate Similarity	0.7488	NPC264176
Intermediate Similarity	0.7488	NPC472098
Intermediate Similarity	0.7488	NPC267928
Intermediate Similarity	0.7487	NPC234392
Intermediate Similarity	0.7487	NPC31311
Intermediate Similarity	0.7478	NPC15406
Intermediate Similarity	0.7476	NPC131017
Intermediate Similarity	0.7467	NPC469554
Intermediate Similarity	0.7464	NPC329793
Intermediate Similarity	0.7464	NPC315957
Intermediate Similarity	0.7464	NPC329747
Intermediate Similarity	0.7456	NPC11408
Intermediate Similarity	0.7453	NPC475841
Intermediate Similarity	0.7453	NPC474145
Intermediate Similarity	0.7452	NPC127085
Intermediate Similarity	0.7451	NPC474904
Intermediate Similarity	0.7441	NPC469440
Intermediate Similarity	0.7441	NPC162484
Intermediate Similarity	0.743	NPC201697
Intermediate Similarity	0.7418	NPC193777
Intermediate Similarity	0.7407	NPC26679
Intermediate Similarity	0.7406	NPC164374
Intermediate Similarity	0.7406	NPC137929
Intermediate Similarity	0.7401	NPC473184
Intermediate Similarity	0.7399	NPC200888
Intermediate Similarity	0.7389	NPC101543
Intermediate Similarity	0.7387	NPC285941
Intermediate Similarity	0.7383	NPC287208
Intermediate Similarity	0.7383	NPC475910
Intermediate Similarity	0.7376	NPC310118
Intermediate Similarity	0.7373	NPC471080
Intermediate Similarity	0.7373	NPC469592
Intermediate Similarity	0.7371	NPC304183
Intermediate Similarity	0.7368	NPC26872
Intermediate Similarity	0.7368	NPC72211
Intermediate Similarity	0.7368	NPC23080
Intermediate Similarity	0.7368	NPC193906
Intermediate Similarity	0.7366	NPC110151
Intermediate Similarity	0.7364	NPC17565
Intermediate Similarity	0.7363	NPC470474
Intermediate Similarity	0.7358	NPC245816
Intermediate Similarity	0.7358	NPC476138
Intermediate Similarity	0.7356	NPC473053
Intermediate Similarity	0.7356	NPC162653
Intermediate Similarity	0.7349	NPC185782
Intermediate Similarity	0.7347	NPC232514
Intermediate Similarity	0.7347	NPC276944
Intermediate Similarity	0.7347	NPC238530
Intermediate Similarity	0.7346	NPC267423
Intermediate Similarity	0.7344	NPC132385
Intermediate Similarity	0.7333	NPC471178
Intermediate Similarity	0.7333	NPC212163
Intermediate Similarity	0.733	NPC233029
Intermediate Similarity	0.733	NPC210148
Intermediate Similarity	0.733	NPC472099
Intermediate Similarity	0.733	NPC469390
Intermediate Similarity	0.733	NPC477533

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
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