NPASS drugs

Drug Information

Drug ID:	NPD2166
Drug Name:	Renzapride
Molecular Formula:	C16H22ClN3O2
Canonical SMILES:	COc1c(ccc(c1Cl)N)C(=NC1CCN2CC1CCC2)O
Standard InCHI:	InChI=1S/C16H22ClN3O2/c1-22-15-11(4-5-12(18)14(15)17)16(21)19-13-6-8-20-7-2-3-10(13)9-20/h4-5,10,13H,2-3,6-9,18H2,1H3,(H,19,21)
Standard InCHIKey:	YFUAYKVMQVBSNG-UHFFFAOYSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD2166

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	267
0.1-0.2	2299
0.2-0.3	10131
0.3-0.4	3651
0.4-0.5	11760
0.5-0.6	2565
0.6-0.7	216
0.7-0.8	1
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	0.7062	NPC28510
Remote Similarity	0.6828	NPC238430
Remote Similarity	0.6735	NPC232872
Remote Similarity	0.6715	NPC475910
Remote Similarity	0.6682	NPC274268
Remote Similarity	0.6648	NPC219383
Remote Similarity	0.6533	NPC295287
Remote Similarity	0.6531	NPC272375
Remote Similarity	0.6528	NPC168153
Remote Similarity	0.6526	NPC208280
Remote Similarity	0.6458	NPC310894
Remote Similarity	0.6456	NPC329747
Remote Similarity	0.6443	NPC473432
Remote Similarity	0.6429	NPC70092
Remote Similarity	0.641	NPC283152
Remote Similarity	0.641	NPC127082
Remote Similarity	0.6406	NPC269383
Remote Similarity	0.6406	NPC151030
Remote Similarity	0.6404	NPC203972
Remote Similarity	0.6402	NPC469592
Remote Similarity	0.6402	NPC471080
Remote Similarity	0.6382	NPC474498
Remote Similarity	0.6382	NPC473007
Remote Similarity	0.6368	NPC168250
Remote Similarity	0.6368	NPC217294
Remote Similarity	0.636	NPC49583
Remote Similarity	0.634	NPC49315
Remote Similarity	0.634	NPC225381
Remote Similarity	0.6337	NPC174629
Remote Similarity	0.6337	NPC474059
Remote Similarity	0.6327	NPC9475
Remote Similarity	0.6311	NPC70956
Remote Similarity	0.6311	NPC243834
Remote Similarity	0.6302	NPC19555
Remote Similarity	0.6298	NPC329793
Remote Similarity	0.6296	NPC291359
Remote Similarity	0.6296	NPC29647
Remote Similarity	0.6296	NPC189661
Remote Similarity	0.6291	NPC469589
Remote Similarity	0.6284	NPC469594
Remote Similarity	0.6281	NPC98197
Remote Similarity	0.6277	NPC315257
Remote Similarity	0.6276	NPC288943
Remote Similarity	0.6275	NPC204970
Remote Similarity	0.6267	NPC152768
Remote Similarity	0.6267	NPC148183
Remote Similarity	0.6263	NPC45112
Remote Similarity	0.6263	NPC271958
Remote Similarity	0.6263	NPC134413
Remote Similarity	0.6263	NPC263507
Remote Similarity	0.6263	NPC79328
Remote Similarity	0.6256	NPC473008
Remote Similarity	0.625	NPC62069
Remote Similarity	0.625	NPC471178
Remote Similarity	0.625	NPC478074
Remote Similarity	0.623	NPC124542
Remote Similarity	0.623	NPC59779
Remote Similarity	0.623	NPC471177
Remote Similarity	0.623	NPC177404
Remote Similarity	0.623	NPC72291
Remote Similarity	0.6226	NPC472111
Remote Similarity	0.6207	NPC477186
Remote Similarity	0.6203	NPC184161
Remote Similarity	0.62	NPC86678
Remote Similarity	0.62	NPC133306
Remote Similarity	0.619	NPC10730
Remote Similarity	0.619	NPC10875
Remote Similarity	0.619	NPC232600
Remote Similarity	0.6181	NPC283999
Remote Similarity	0.6173	NPC66573
Remote Similarity	0.6168	NPC470931
Remote Similarity	0.6165	NPC289786
Remote Similarity	0.6161	NPC291535
Remote Similarity	0.6161	NPC475085
Remote Similarity	0.6161	NPC475112
Remote Similarity	0.6161	NPC474077
Remote Similarity	0.6158	NPC110416
Remote Similarity	0.6158	NPC204828
Remote Similarity	0.6158	NPC469817
Remote Similarity	0.6158	NPC276588
Remote Similarity	0.6158	NPC54379
Remote Similarity	0.6158	NPC278799
Remote Similarity	0.6158	NPC127674
Remote Similarity	0.6158	NPC207757
Remote Similarity	0.6158	NPC193949
Remote Similarity	0.6158	NPC2413
Remote Similarity	0.6158	NPC184026
Remote Similarity	0.6158	NPC249797
Remote Similarity	0.6158	NPC469830
Remote Similarity	0.6158	NPC172765
Remote Similarity	0.6158	NPC189266
Remote Similarity	0.6158	NPC5238
Remote Similarity	0.6158	NPC295691
Remote Similarity	0.6158	NPC39701
Remote Similarity	0.6154	NPC472191
Remote Similarity	0.6154	NPC43275
Remote Similarity	0.6154	NPC257354
Remote Similarity	0.6154	NPC272706
Remote Similarity	0.6154	NPC477888
Remote Similarity	0.615	NPC476106
Remote Similarity	0.6132	NPC473460
Remote Similarity	0.6129	NPC476151
Remote Similarity	0.6127	NPC325013
Remote Similarity	0.6126	NPC84508
Remote Similarity	0.6121	NPC194699
Remote Similarity	0.6121	NPC219350
Remote Similarity	0.6117	NPC141915
Remote Similarity	0.6117	NPC114335
Remote Similarity	0.6117	NPC280964
Remote Similarity	0.6116	NPC166655
Remote Similarity	0.6114	NPC472329
Remote Similarity	0.6114	NPC472330
Remote Similarity	0.6111	NPC166667
Remote Similarity	0.6109	NPC108826
Remote Similarity	0.6108	NPC33902
Remote Similarity	0.6108	NPC276674
Remote Similarity	0.6106	NPC303214
Remote Similarity	0.6105	NPC477564
Remote Similarity	0.6105	NPC2295
Remote Similarity	0.6103	NPC209377
Remote Similarity	0.6103	NPC473422
Remote Similarity	0.6102	NPC476687
Remote Similarity	0.6102	NPC476685
Remote Similarity	0.6102	NPC476689
Remote Similarity	0.6099	NPC212850
Remote Similarity	0.6099	NPC189724
Remote Similarity	0.6099	NPC83289
Remote Similarity	0.6098	NPC226914
Remote Similarity	0.6096	NPC7467
Remote Similarity	0.6085	NPC26872
Remote Similarity	0.6082	NPC204179
Remote Similarity	0.6078	NPC66083
Remote Similarity	0.6075	NPC245974
Remote Similarity	0.6073	NPC469428
Remote Similarity	0.6073	NPC26850
Remote Similarity	0.6071	NPC193853
Remote Similarity	0.6071	NPC13916
Remote Similarity	0.6071	NPC264850
Remote Similarity	0.6071	NPC56887
Remote Similarity	0.6071	NPC223077
Remote Similarity	0.6071	NPC195392
Remote Similarity	0.607	NPC473105
Remote Similarity	0.6068	NPC22476
Remote Similarity	0.6064	NPC207824
Remote Similarity	0.6064	NPC477565
Remote Similarity	0.6064	NPC103379
Remote Similarity	0.6064	NPC60538
Remote Similarity	0.6063	NPC473041
Remote Similarity	0.6062	NPC289776
Remote Similarity	0.6062	NPC216816
Remote Similarity	0.6062	NPC191863
Remote Similarity	0.6062	NPC133470
Remote Similarity	0.6062	NPC221864
Remote Similarity	0.6059	NPC42591
Remote Similarity	0.6058	NPC230313
Remote Similarity	0.6055	NPC202605
Remote Similarity	0.6055	NPC112206
Remote Similarity	0.6054	NPC247298
Remote Similarity	0.605	NPC232340
Remote Similarity	0.6048	NPC100863
Remote Similarity	0.6048	NPC72211
Remote Similarity	0.6047	NPC193777
Remote Similarity	0.6043	NPC51957
Remote Similarity	0.6043	NPC476144
Remote Similarity	0.6043	NPC210437
Remote Similarity	0.6043	NPC106295
Remote Similarity	0.6043	NPC16107
Remote Similarity	0.6039	NPC114039
Remote Similarity	0.6039	NPC206109
Remote Similarity	0.6036	NPC213530
Remote Similarity	0.6036	NPC193267
Remote Similarity	0.6031	NPC205255
Remote Similarity	0.6031	NPC119649
Remote Similarity	0.6031	NPC230956
Remote Similarity	0.6031	NPC235143
Remote Similarity	0.6031	NPC271388
Remote Similarity	0.6028	NPC118832
Remote Similarity	0.6028	NPC329708
Remote Similarity	0.6028	NPC264166
Remote Similarity	0.6028	NPC47059
Remote Similarity	0.6028	NPC165349
Remote Similarity	0.6028	NPC274291
Remote Similarity	0.6023	NPC17388
Remote Similarity	0.6023	NPC53596
Remote Similarity	0.6023	NPC471308
Remote Similarity	0.6023	NPC160120
Remote Similarity	0.6023	NPC289330
Remote Similarity	0.6022	NPC185838
Remote Similarity	0.6022	NPC472100
Remote Similarity	0.602	NPC121275
Remote Similarity	0.602	NPC24465
Remote Similarity	0.602	NPC4138
Remote Similarity	0.602	NPC284183
Remote Similarity	0.602	NPC265383
Remote Similarity	0.6019	NPC329329
Remote Similarity	0.6019	NPC317709
Remote Similarity	0.6019	NPC473569
Remote Similarity	0.6018	NPC305984
Remote Similarity	0.6012	NPC471314
Remote Similarity	0.6012	NPC471315

Drug Structure

NPD2166 OpenBabel08211701392D 25 27 0 0 1 0 0 0 0 0999 V2000 1.6732 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4112 -0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6425 -0.2849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8366 -1.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6732 -0.9660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6182 -0.5858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8454 0.4096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1182 0.2802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6182 1.1462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1182 0.2802 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -0.9660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6732 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6182 -0.5858 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8366 0.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8366 -1.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8366 1.4491 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.5099 0.4830 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8366 -2.4151 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6182 1.1462 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.6732 -0.9660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8366 0.4830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5099 1.4491 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3465 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1563 -0.1294 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 1 0 0 0 0 2 7 1 0 0 0 0 3 10 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 13 1 0 0 0 0 7 20 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 22 1 0 0 0 0 16 19 2 3 0 0 0 16 21 1 0 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank	DB04917
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number	112727-80-7

Drug Properties

Molecular Weight	323.14
ALogP	-0.88
MLogP	2.56
XLogP	1.705
HDA	4
HBD	2
Rotatable Bonds	7
TPSA	71.08
RO5 Violation	0