NPASS drugs

Drug Information

Drug ID:	NPD5891
Drug Name:	Nicergoline
Molecular Formula:	C24H26BrN3O3
Canonical SMILES:	CO[C@]12C[C@@H](COC(=O)c3cncc(c3)Br)CN([C@@H]1Cc1c3c2cccc3n(c1)C)C
Standard InCHI:	InChI=1S/C24H26BrN3O3/c1-27-13-17-8-21-24(30-3,19-5-4-6-20(27)22(17)19)9-15(12-28(21)2)14-31-23(29)16-7-18(25)11-26-10-16/h4-7,10-11,13,15,21H,8-9,12,14H2,1-3H3/t15-,21-,24+/m1/s1
Standard InCHIKey:	YSEXMKHXIOCEJA-FVFQAYNVSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD5891

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	366
0.1-0.2	1685
0.2-0.3	7876
0.3-0.4	12072
0.4-0.5	5729
0.5-0.6	1685
0.6-0.7	1289
0.7-0.8	188
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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
Intermediate Similarity	0.7844	NPC289086
Intermediate Similarity	0.7735	NPC327769
Intermediate Similarity	0.7686	NPC477788
Intermediate Similarity	0.7619	NPC477899
Intermediate Similarity	0.7619	NPC477900
Intermediate Similarity	0.7598	NPC477901
Intermediate Similarity	0.7586	NPC473506
Intermediate Similarity	0.7574	NPC49547
Intermediate Similarity	0.7555	NPC472555
Intermediate Similarity	0.7554	NPC122968
Intermediate Similarity	0.7554	NPC228377
Intermediate Similarity	0.7554	NPC476110
Intermediate Similarity	0.7554	NPC475600
Intermediate Similarity	0.7554	NPC74575
Intermediate Similarity	0.7554	NPC475631
Intermediate Similarity	0.7554	NPC328186
Intermediate Similarity	0.7554	NPC477787
Intermediate Similarity	0.7554	NPC87152
Intermediate Similarity	0.7544	NPC477908
Intermediate Similarity	0.7544	NPC206343
Intermediate Similarity	0.7533	NPC4421
Intermediate Similarity	0.7532	NPC316841
Intermediate Similarity	0.7532	NPC473689
Intermediate Similarity	0.7532	NPC235364
Intermediate Similarity	0.7532	NPC475596
Intermediate Similarity	0.7532	NPC292416
Intermediate Similarity	0.7532	NPC475303
Intermediate Similarity	0.7522	NPC318299
Intermediate Similarity	0.7521	NPC470486
Intermediate Similarity	0.7521	NPC471190
Intermediate Similarity	0.7521	NPC475644
Intermediate Similarity	0.7521	NPC471977
Intermediate Similarity	0.7511	NPC473115
Intermediate Similarity	0.7511	NPC158020
Intermediate Similarity	0.7511	NPC475406
Intermediate Similarity	0.7511	NPC75600
Intermediate Similarity	0.7511	NPC6576
Intermediate Similarity	0.7511	NPC212768
Intermediate Similarity	0.7511	NPC473089
Intermediate Similarity	0.75	NPC30456
Intermediate Similarity	0.75	NPC319880
Intermediate Similarity	0.75	NPC57797
Intermediate Similarity	0.75	NPC244839
Intermediate Similarity	0.75	NPC250807
Intermediate Similarity	0.75	NPC320324
Intermediate Similarity	0.75	NPC76565
Intermediate Similarity	0.7489	NPC317752
Intermediate Similarity	0.7489	NPC82053
Intermediate Similarity	0.7489	NPC477903
Intermediate Similarity	0.7479	NPC146824
Intermediate Similarity	0.7479	NPC38959
Intermediate Similarity	0.7479	NPC327904
Intermediate Similarity	0.7468	NPC473850
Intermediate Similarity	0.7468	NPC237702
Intermediate Similarity	0.7468	NPC475137
Intermediate Similarity	0.7468	NPC26881
Intermediate Similarity	0.7468	NPC475498
Intermediate Similarity	0.7467	NPC6981
Intermediate Similarity	0.7457	NPC477911
Intermediate Similarity	0.7456	NPC264674
Intermediate Similarity	0.7455	NPC123395
Intermediate Similarity	0.7447	NPC475362
Intermediate Similarity	0.7445	NPC118940
Intermediate Similarity	0.7444	NPC327592
Intermediate Similarity	0.7437	NPC170751
Intermediate Similarity	0.7436	NPC470018
Intermediate Similarity	0.7435	NPC294579
Intermediate Similarity	0.7435	NPC144779
Intermediate Similarity	0.7434	NPC123839
Intermediate Similarity	0.7415	NPC91125
Intermediate Similarity	0.7411	NPC317373
Intermediate Similarity	0.7403	NPC84815
Intermediate Similarity	0.7403	NPC301368
Intermediate Similarity	0.7397	NPC472116
Intermediate Similarity	0.7395	NPC329631
Intermediate Similarity	0.7383	NPC282103
Intermediate Similarity	0.7382	NPC127026
Intermediate Similarity	0.7382	NPC127720
Intermediate Similarity	0.7359	NPC62367
Intermediate Similarity	0.735	NPC322482
Intermediate Similarity	0.735	NPC471980
Intermediate Similarity	0.7348	NPC477909
Intermediate Similarity	0.7348	NPC477907
Intermediate Similarity	0.7348	NPC470306
Intermediate Similarity	0.7348	NPC42678
Intermediate Similarity	0.7345	NPC63041
Intermediate Similarity	0.7345	NPC266249
Intermediate Similarity	0.7333	NPC238457
Intermediate Similarity	0.733	NPC474916
Intermediate Similarity	0.7328	NPC216428
Intermediate Similarity	0.7319	NPC477902
Intermediate Similarity	0.7318	NPC245916
Intermediate Similarity	0.7317	NPC270515
Intermediate Similarity	0.7316	NPC475408
Intermediate Similarity	0.7316	NPC471014
Intermediate Similarity	0.7316	NPC471016
Intermediate Similarity	0.7314	NPC253482
Intermediate Similarity	0.7313	NPC472550
Intermediate Similarity	0.7313	NPC304179
Intermediate Similarity	0.7313	NPC48042
Intermediate Similarity	0.7311	NPC477906
Intermediate Similarity	0.7303	NPC470022
Intermediate Similarity	0.7295	NPC475648
Intermediate Similarity	0.7293	NPC472553
Intermediate Similarity	0.7281	NPC470020
Intermediate Similarity	0.7277	NPC57398
Intermediate Similarity	0.7273	NPC135950
Intermediate Similarity	0.7273	NPC251936
Intermediate Similarity	0.7265	NPC208522
Intermediate Similarity	0.7265	NPC477912
Intermediate Similarity	0.7257	NPC211920
Intermediate Similarity	0.7257	NPC124029
Intermediate Similarity	0.7246	NPC328154
Intermediate Similarity	0.7234	NPC216612
Intermediate Similarity	0.7222	NPC472099
Intermediate Similarity	0.722	NPC35208
Intermediate Similarity	0.722	NPC475426
Intermediate Similarity	0.722	NPC103361
Intermediate Similarity	0.7217	NPC84347
Intermediate Similarity	0.7215	NPC138370
Intermediate Similarity	0.72	NPC328318
Intermediate Similarity	0.72	NPC328596
Intermediate Similarity	0.7198	NPC477910
Intermediate Similarity	0.7198	NPC36405
Intermediate Similarity	0.7193	NPC470280
Intermediate Similarity	0.719	NPC470017
Intermediate Similarity	0.7188	NPC470279
Intermediate Similarity	0.7186	NPC165837
Intermediate Similarity	0.7184	NPC72905
Intermediate Similarity	0.7172	NPC471583
Intermediate Similarity	0.7172	NPC471782
Intermediate Similarity	0.7156	NPC249614
Intermediate Similarity	0.7155	NPC228331
Intermediate Similarity	0.7155	NPC319128
Intermediate Similarity	0.7149	NPC314297
Intermediate Similarity	0.7149	NPC315545
Intermediate Similarity	0.7149	NPC198673
Intermediate Similarity	0.7143	NPC475778
Intermediate Similarity	0.7143	NPC148860
Intermediate Similarity	0.7143	NPC472098
Intermediate Similarity	0.7131	NPC278540
Intermediate Similarity	0.713	NPC234999
Intermediate Similarity	0.713	NPC314834
Intermediate Similarity	0.7112	NPC221100
Intermediate Similarity	0.7112	NPC234078
Intermediate Similarity	0.7105	NPC315638
Intermediate Similarity	0.7105	NPC314855
Intermediate Similarity	0.7105	NPC313345
Intermediate Similarity	0.7105	NPC313796
Intermediate Similarity	0.7098	NPC168911
Intermediate Similarity	0.7097	NPC472119
Intermediate Similarity	0.7095	NPC150698
Intermediate Similarity	0.7095	NPC96801
Intermediate Similarity	0.7095	NPC260434
Intermediate Similarity	0.7095	NPC474688
Intermediate Similarity	0.7085	NPC142385
Intermediate Similarity	0.7082	NPC477979
Intermediate Similarity	0.7075	NPC478083
Intermediate Similarity	0.7072	NPC103230
Intermediate Similarity	0.707	NPC328928
Intermediate Similarity	0.7069	NPC264176
Intermediate Similarity	0.7067	NPC81535
Intermediate Similarity	0.7061	NPC132539
Intermediate Similarity	0.7056	NPC311451
Intermediate Similarity	0.7052	NPC137353
Intermediate Similarity	0.7051	NPC143533
Intermediate Similarity	0.7049	NPC477549
Intermediate Similarity	0.7048	NPC162730
Intermediate Similarity	0.7043	NPC132385
Intermediate Similarity	0.7042	NPC14116
Intermediate Similarity	0.7042	NPC285411
Intermediate Similarity	0.7042	NPC475601
Intermediate Similarity	0.7037	NPC70155
Intermediate Similarity	0.7035	NPC214428
Intermediate Similarity	0.7032	NPC66210
Intermediate Similarity	0.7024	NPC471536
Intermediate Similarity	0.7022	NPC239954
Intermediate Similarity	0.702	NPC216369
Intermediate Similarity	0.7018	NPC258480
Intermediate Similarity	0.7017	NPC469312
Intermediate Similarity	0.7017	NPC144452
Intermediate Similarity	0.7017	NPC41318
Intermediate Similarity	0.7017	NPC210434
Intermediate Similarity	0.7014	NPC95783
Intermediate Similarity	0.7012	NPC311196
Intermediate Similarity	0.7012	NPC134384
Intermediate Similarity	0.7008	NPC253675
Intermediate Similarity	0.7	NPC475835
Remote Similarity	0.6996	NPC280473
Remote Similarity	0.6996	NPC323551
Remote Similarity	0.6996	NPC213143
Remote Similarity	0.6987	NPC314648
Remote Similarity	0.6987	NPC229893
Remote Similarity	0.6983	NPC278525
Remote Similarity	0.6982	NPC472097
Remote Similarity	0.6979	NPC207531
Remote Similarity	0.6975	NPC280799
Remote Similarity	0.6974	NPC474116
Remote Similarity	0.6967	NPC22481
Remote Similarity	0.6966	NPC41724

Drug Structure

NPD5891 OpenBabel08211708292D 31 35 0 0 1 0 0 0 0 0999 V2000 4.8795 -1.6172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 0.9617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0294 -2.7885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3750 -3.1985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5834 -2.7415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1663 -2.7415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1229 -0.4102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5830 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0004 -1.8280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9554 -1.8529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7886 -0.4106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7914 -0.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1661 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6240 -1.8522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7912 -1.3712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1227 -1.3719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3748 -0.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9559 0.0705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5834 -1.8278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1664 -1.8274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7916 -0.4568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3747 -1.3708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2897 -1.8526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7918 -1.3708 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9561 1.0322 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -5.7884 -1.3723 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9577 -1.3704 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2895 -2.8143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7921 -2.2848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4569 -1.3715 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 28 1 0 0 0 0 3 30 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 19 1 0 0 0 0 6 20 2 0 0 0 0 7 16 2 0 0 0 0 7 18 1 0 0 0 0 8 17 1 0 0 0 0 8 21 1 0 0 0 0 9 15 1 0 0 0 0 9 24 1 0 0 0 0 10 16 1 0 0 0 0 10 26 2 0 0 0 0 11 18 2 0 0 0 0 11 26 1 0 0 0 0 12 15 1 0 0 0 0 12 28 1 0 0 0 0 13 17 2 0 0 0 0 13 27 1 0 0 0 0 14 31 1 0 0 0 0 15 14 1 1 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 18 25 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 6 0 0 0 21 28 1 0 0 0 0 23 29 2 0 0 0 0 23 31 1 0 0 0 0 24 30 1 6 0 0 0 M END $$$$

External Identifiers

TTD	DAP000902
DrugBank	DB00699
ChEMBL	CHEMBL1372950
IUPHAR/BPS
PharmaGKB	PA164743014
KEGG Drug	D01290
PubChem CID	34040
ChEBI	31902
CAS Number	27848-84-6

Drug Properties

Molecular Weight	483.12
ALogP	0.4835
MLogP	3.33
XLogP	3.297
HDA	6
HBD	0
Rotatable Bonds	9
TPSA	56.59
RO5 Violation	0