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.


  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

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