NPASS drugs

Drug Information

Drug ID:	NPD5016
Drug Name:	Benperidol
Molecular Formula:	C22H24FN3O2
Canonical SMILES:	Fc1ccc(cc1)C(=O)CCCN1CCC(CC1)n1c(O)nc2c1cccc2
Standard InCHI:	InChI=1S/C22H24FN3O2/c23-17-9-7-16(8-10-17)21(27)6-3-13-25-14-11-18(12-15-25)26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-5,7-10,18H,3,6,11-15H2,(H,24,28)
Standard InCHIKey:	FEBOTPHFXYHVPL-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5016

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	377
0.1-0.2	3139
0.2-0.3	11587
0.3-0.4	11534
0.4-0.5	1835
0.5-0.6	1865
0.6-0.7	531
0.7-0.8	21
0.8-0.85	0
0.85-0.9	1
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
High Similarity	0.8596	NPC476341
Intermediate Similarity	0.7463	NPC116555
Intermediate Similarity	0.7292	NPC135601
Intermediate Similarity	0.7292	NPC141612
Intermediate Similarity	0.7292	NPC17273
Intermediate Similarity	0.7277	NPC21429
Intermediate Similarity	0.726	NPC267811
Intermediate Similarity	0.7232	NPC114209
Intermediate Similarity	0.7211	NPC73994
Intermediate Similarity	0.7181	NPC317054
Intermediate Similarity	0.7135	NPC470205
Intermediate Similarity	0.7092	NPC324091
Intermediate Similarity	0.7047	NPC243058
Intermediate Similarity	0.7037	NPC252572
Intermediate Similarity	0.7033	NPC476219
Intermediate Similarity	0.7031	NPC88110
Intermediate Similarity	0.7027	NPC478185
Intermediate Similarity	0.7016	NPC83774
Intermediate Similarity	0.7015	NPC474916
Intermediate Similarity	0.701	NPC285923
Intermediate Similarity	0.701	NPC203635
Intermediate Similarity	0.7005	NPC56233
Remote Similarity	0.6989	NPC271797
Remote Similarity	0.6989	NPC21174
Remote Similarity	0.6989	NPC478182
Remote Similarity	0.6985	NPC326422
Remote Similarity	0.6974	NPC133003
Remote Similarity	0.6943	NPC15840
Remote Similarity	0.6943	NPC61011
Remote Similarity	0.694	NPC476297
Remote Similarity	0.6939	NPC90415
Remote Similarity	0.6935	NPC194881
Remote Similarity	0.6927	NPC157583
Remote Similarity	0.6927	NPC219848
Remote Similarity	0.6919	NPC293487
Remote Similarity	0.6908	NPC243850
Remote Similarity	0.6907	NPC113626
Remote Similarity	0.6907	NPC191415
Remote Similarity	0.6891	NPC256268
Remote Similarity	0.6889	NPC478186
Remote Similarity	0.6875	NPC151635
Remote Similarity	0.685	NPC272458
Remote Similarity	0.6839	NPC234987
Remote Similarity	0.6837	NPC258480
Remote Similarity	0.6837	NPC46895
Remote Similarity	0.6833	NPC935
Remote Similarity	0.6833	NPC267078
Remote Similarity	0.6832	NPC128244
Remote Similarity	0.6832	NPC472116
Remote Similarity	0.6825	NPC478183
Remote Similarity	0.6823	NPC469529
Remote Similarity	0.6814	NPC81535
Remote Similarity	0.6809	NPC478184
Remote Similarity	0.6808	NPC177996
Remote Similarity	0.6808	NPC62995
Remote Similarity	0.6808	NPC147983
Remote Similarity	0.6802	NPC474357
Remote Similarity	0.6786	NPC159125
Remote Similarity	0.6786	NPC471609
Remote Similarity	0.6779	NPC471191
Remote Similarity	0.6777	NPC72956
Remote Similarity	0.6769	NPC24864
Remote Similarity	0.6763	NPC317701
Remote Similarity	0.6754	NPC471943
Remote Similarity	0.6754	NPC32534
Remote Similarity	0.6753	NPC237188
Remote Similarity	0.6748	NPC469308
Remote Similarity	0.6745	NPC153980
Remote Similarity	0.6745	NPC6865
Remote Similarity	0.6745	NPC471603
Remote Similarity	0.6738	NPC300238
Remote Similarity	0.6734	NPC472323
Remote Similarity	0.6731	NPC472259
Remote Similarity	0.6722	NPC42483
Remote Similarity	0.672	NPC265100
Remote Similarity	0.6716	NPC167710
Remote Similarity	0.6714	NPC282247
Remote Similarity	0.6712	NPC470323
Remote Similarity	0.6703	NPC281094
Remote Similarity	0.6701	NPC102755
Remote Similarity	0.67	NPC255909
Remote Similarity	0.6684	NPC2165
Remote Similarity	0.6684	NPC195507
Remote Similarity	0.6683	NPC478077
Remote Similarity	0.6683	NPC66210
Remote Similarity	0.6683	NPC216550
Remote Similarity	0.6667	NPC471194
Remote Similarity	0.6667	NPC471193
Remote Similarity	0.6667	NPC102592
Remote Similarity	0.6667	NPC79356
Remote Similarity	0.6667	NPC284775
Remote Similarity	0.6651	NPC471192
Remote Similarity	0.665	NPC477891
Remote Similarity	0.6649	NPC114637
Remote Similarity	0.6649	NPC217021
Remote Similarity	0.6649	NPC470679
Remote Similarity	0.6649	NPC469938
Remote Similarity	0.6635	NPC57398
Remote Similarity	0.6635	NPC71238
Remote Similarity	0.6633	NPC12649
Remote Similarity	0.6617	NPC472289
Remote Similarity	0.6611	NPC238499
Remote Similarity	0.6598	NPC208060
Remote Similarity	0.6598	NPC161861
Remote Similarity	0.6595	NPC473878
Remote Similarity	0.6592	NPC116622
Remote Similarity	0.6583	NPC477003
Remote Similarity	0.6583	NPC472119
Remote Similarity	0.658	NPC91895
Remote Similarity	0.6579	NPC242116
Remote Similarity	0.6579	NPC470203
Remote Similarity	0.6573	NPC216159
Remote Similarity	0.6569	NPC304203
Remote Similarity	0.6566	NPC144114
Remote Similarity	0.6561	NPC80681
Remote Similarity	0.6559	NPC469975
Remote Similarity	0.6559	NPC117032
Remote Similarity	0.6557	NPC204141
Remote Similarity	0.6556	NPC471574
Remote Similarity	0.6552	NPC476460
Remote Similarity	0.655	NPC79062
Remote Similarity	0.655	NPC472107
Remote Similarity	0.6542	NPC54981
Remote Similarity	0.6541	NPC282531
Remote Similarity	0.6538	NPC121327
Remote Similarity	0.6538	NPC20144
Remote Similarity	0.6536	NPC65408
Remote Similarity	0.6533	NPC143533
Remote Similarity	0.6528	NPC70949
Remote Similarity	0.6526	NPC470204
Remote Similarity	0.6524	NPC200743
Remote Similarity	0.6517	NPC62749
Remote Similarity	0.6515	NPC16659
Remote Similarity	0.6512	NPC473218
Remote Similarity	0.6512	NPC470702
Remote Similarity	0.6505	NPC40070
Remote Similarity	0.6502	NPC472112
Remote Similarity	0.6502	NPC187145
Remote Similarity	0.65	NPC207554
Remote Similarity	0.65	NPC467063
Remote Similarity	0.65	NPC470003
Remote Similarity	0.6498	NPC322064
Remote Similarity	0.6493	NPC314648
Remote Similarity	0.6492	NPC225018
Remote Similarity	0.649	NPC237414
Remote Similarity	0.6489	NPC120070
Remote Similarity	0.6486	NPC470111
Remote Similarity	0.6484	NPC48317
Remote Similarity	0.6481	NPC470703
Remote Similarity	0.6476	NPC143977
Remote Similarity	0.6471	NPC472260
Remote Similarity	0.6471	NPC70406
Remote Similarity	0.6471	NPC63109
Remote Similarity	0.6471	NPC220851
Remote Similarity	0.6471	NPC117244
Remote Similarity	0.6471	NPC473763
Remote Similarity	0.6468	NPC99939
Remote Similarity	0.6468	NPC27041
Remote Similarity	0.6468	NPC308931
Remote Similarity	0.6465	NPC265710
Remote Similarity	0.6464	NPC104483
Remote Similarity	0.6462	NPC313796
Remote Similarity	0.6462	NPC313345
Remote Similarity	0.6462	NPC314855
Remote Similarity	0.6462	NPC6982
Remote Similarity	0.6462	NPC315638
Remote Similarity	0.6461	NPC300299
Remote Similarity	0.645	NPC171393
Remote Similarity	0.645	NPC295452
Remote Similarity	0.645	NPC117027
Remote Similarity	0.6448	NPC136002
Remote Similarity	0.6444	NPC74619
Remote Similarity	0.6441	NPC476817
Remote Similarity	0.6432	NPC315545
Remote Similarity	0.6432	NPC314297
Remote Similarity	0.6425	NPC115232
Remote Similarity	0.6425	NPC245916
Remote Similarity	0.6421	NPC477887
Remote Similarity	0.6421	NPC76982
Remote Similarity	0.6414	NPC28848
Remote Similarity	0.6414	NPC14325
Remote Similarity	0.641	NPC164664
Remote Similarity	0.641	NPC65080
Remote Similarity	0.6408	NPC247735
Remote Similarity	0.6408	NPC81802
Remote Similarity	0.6408	NPC269886
Remote Similarity	0.6408	NPC472210
Remote Similarity	0.6408	NPC472295
Remote Similarity	0.6406	NPC224632
Remote Similarity	0.6398	NPC100726
Remote Similarity	0.6394	NPC227582
Remote Similarity	0.6393	NPC277157
Remote Similarity	0.639	NPC472097
Remote Similarity	0.6385	NPC238457
Remote Similarity	0.6385	NPC472064
Remote Similarity	0.6382	NPC11126
Remote Similarity	0.6382	NPC248462
Remote Similarity	0.638	NPC272174
Remote Similarity	0.6378	NPC105758
Remote Similarity	0.6378	NPC476686

Drug Structure

NPD5016 OpenBabel08211706322D 29 32 0 0 0 0 0 0 0 0999 V2000 2.8698 -0.8226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2007 -1.5657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5608 0.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2226 -1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -2.0000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6386 1.6637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4307 2.6418 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 13 1 0 0 0 0 4 19 2 0 0 0 0 5 20 2 0 0 0 0 6 21 1 0 0 0 0 7 9 1 0 0 0 0 7 16 2 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 25 1 0 0 0 0 14 25 1 0 0 0 0 15 25 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 26 1 0 0 0 0 21 27 2 0 0 0 0 22 24 2 0 0 0 0 22 26 1 0 0 0 0 22 28 1 0 0 0 0 28 29 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB003612
DrugBank
ChEMBL
IUPHAR/BPS	9215
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	381.19
ALogP	-1.0628
MLogP	3.22
XLogP	4.095
HDA	4
HBD	1
Rotatable Bonds	8
TPSA	58.36
RO5 Violation	0