NPASS drugs

Drug Information

Drug ID:	NPD5652
Drug Name:	Cisapride
Molecular Formula:	C23H29ClFN3O4
Canonical SMILES:	CO[C@H]1CN(CCCOc2ccc(cc2)F)CC[C@H]1N=C(c1cc(Cl)c(cc1OC)N)O
Standard InCHI:	InChI=1S/C23H29ClFN3O4/c1-30-21-13-19(26)18(24)12-17(21)23(29)27-20-8-10-28(14-22(20)31-2)9-3-11-32-16-6-4-15(25)5-7-16/h4-7,12-13,20,22H,3,8-11,14,26H2,1-2H3,(H,27,29)/t20-,22+/m1/s1
Standard InCHIKey:	DCSUBABJRXZOMT-IRLDBZIGSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD5652

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	269
0.1-0.2	2057
0.2-0.3	10164
0.3-0.4	3055
0.4-0.5	11520
0.5-0.6	3461
0.6-0.7	362
0.7-0.8	2
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	0.7526	NPC232872
Intermediate Similarity	0.7097	NPC315257
Remote Similarity	0.6804	NPC208280
Remote Similarity	0.6802	NPC168153
Remote Similarity	0.6758	NPC212850
Remote Similarity	0.6758	NPC83289
Remote Similarity	0.6758	NPC189724
Remote Similarity	0.6749	NPC469830
Remote Similarity	0.6732	NPC28510
Remote Similarity	0.672	NPC245974
Remote Similarity	0.6703	NPC247298
Remote Similarity	0.662	NPC473460
Remote Similarity	0.6589	NPC473422
Remote Similarity	0.6582	NPC19555
Remote Similarity	0.6556	NPC471953
Remote Similarity	0.655	NPC473432
Remote Similarity	0.6547	NPC274268
Remote Similarity	0.6546	NPC306366
Remote Similarity	0.6531	NPC204179
Remote Similarity	0.6526	NPC472329
Remote Similarity	0.6526	NPC472330
Remote Similarity	0.6517	NPC283152
Remote Similarity	0.65	NPC471080
Remote Similarity	0.65	NPC469592
Remote Similarity	0.6497	NPC238430
Remote Similarity	0.6495	NPC291359
Remote Similarity	0.6495	NPC311357
Remote Similarity	0.6493	NPC314948
Remote Similarity	0.6492	NPC219383
Remote Similarity	0.6492	NPC184161
Remote Similarity	0.6482	NPC310894
Remote Similarity	0.6477	NPC10875
Remote Similarity	0.6477	NPC10730
Remote Similarity	0.6473	NPC295287
Remote Similarity	0.6464	NPC274732
Remote Similarity	0.6457	NPC469594
Remote Similarity	0.645	NPC225381
Remote Similarity	0.6422	NPC475910
Remote Similarity	0.6417	NPC56271
Remote Similarity	0.6415	NPC478049
Remote Similarity	0.6406	NPC476106
Remote Similarity	0.6394	NPC217294
Remote Similarity	0.6393	NPC469589
Remote Similarity	0.639	NPC469831
Remote Similarity	0.6372	NPC214368
Remote Similarity	0.6364	NPC474059
Remote Similarity	0.6364	NPC254700
Remote Similarity	0.6359	NPC469829
Remote Similarity	0.6355	NPC9475
Remote Similarity	0.635	NPC151030
Remote Similarity	0.635	NPC269383
Remote Similarity	0.6343	NPC475085
Remote Similarity	0.6343	NPC291535
Remote Similarity	0.6343	NPC475112
Remote Similarity	0.6329	NPC473007
Remote Similarity	0.6326	NPC329747
Remote Similarity	0.6316	NPC110741
Remote Similarity	0.6314	NPC49583
Remote Similarity	0.631	NPC314113
Remote Similarity	0.6305	NPC288943
Remote Similarity	0.63	NPC329830
Remote Similarity	0.6293	NPC283999
Remote Similarity	0.6286	NPC473008
Remote Similarity	0.6286	NPC174629
Remote Similarity	0.628	NPC62069
Remote Similarity	0.6275	NPC127082
Remote Similarity	0.6269	NPC477888
Remote Similarity	0.6269	NPC257354
Remote Similarity	0.6268	NPC66083
Remote Similarity	0.6263	NPC72291
Remote Similarity	0.6262	NPC243834
Remote Similarity	0.6262	NPC70956
Remote Similarity	0.625	NPC189661
Remote Similarity	0.625	NPC474498
Remote Similarity	0.6244	NPC85381
Remote Similarity	0.6244	NPC471561
Remote Similarity	0.6244	NPC29647
Remote Similarity	0.6244	NPC168250
Remote Similarity	0.6234	NPC473185
Remote Similarity	0.6233	NPC72211
Remote Similarity	0.6232	NPC98197
Remote Similarity	0.6227	NPC198160
Remote Similarity	0.6226	NPC204970
Remote Similarity	0.6223	NPC477837
Remote Similarity	0.6223	NPC477838
Remote Similarity	0.6217	NPC166655
Remote Similarity	0.6214	NPC70092
Remote Similarity	0.6214	NPC134413
Remote Similarity	0.6214	NPC263507
Remote Similarity	0.6214	NPC271958
Remote Similarity	0.6214	NPC45112
Remote Similarity	0.6212	NPC79328
Remote Similarity	0.6212	NPC231862
Remote Similarity	0.6211	NPC108826
Remote Similarity	0.6209	NPC283207
Remote Similarity	0.6207	NPC83198
Remote Similarity	0.6207	NPC49315
Remote Similarity	0.6207	NPC204908
Remote Similarity	0.6205	NPC478074
Remote Similarity	0.6202	NPC320394
Remote Similarity	0.6199	NPC470931
Remote Similarity	0.6197	NPC79293
Remote Similarity	0.6197	NPC279401
Remote Similarity	0.6196	NPC307123
Remote Similarity	0.6196	NPC247018
Remote Similarity	0.6196	NPC97870
Remote Similarity	0.6188	NPC195392
Remote Similarity	0.6188	NPC326333
Remote Similarity	0.6188	NPC471532
Remote Similarity	0.6186	NPC272706
Remote Similarity	0.6186	NPC472191
Remote Similarity	0.6186	NPC234318
Remote Similarity	0.6184	NPC118776
Remote Similarity	0.6182	NPC472111
Remote Similarity	0.6181	NPC191863
Remote Similarity	0.6181	NPC289776
Remote Similarity	0.6181	NPC133470
Remote Similarity	0.6179	NPC475411
Remote Similarity	0.6179	NPC469390
Remote Similarity	0.6172	NPC313886
Remote Similarity	0.6172	NPC315542
Remote Similarity	0.6172	NPC42591
Remote Similarity	0.6166	NPC476151
Remote Similarity	0.6164	NPC162484
Remote Similarity	0.6161	NPC48353
Remote Similarity	0.6161	NPC477186
Remote Similarity	0.6161	NPC116178
Remote Similarity	0.6157	NPC477532
Remote Similarity	0.6154	NPC194699
Remote Similarity	0.6154	NPC300114
Remote Similarity	0.6154	NPC47672
Remote Similarity	0.6154	NPC219350
Remote Similarity	0.615	NPC318805
Remote Similarity	0.615	NPC41122
Remote Similarity	0.615	NPC148183
Remote Similarity	0.615	NPC152768
Remote Similarity	0.6147	NPC232600
Remote Similarity	0.6143	NPC33902
Remote Similarity	0.6143	NPC276674
Remote Similarity	0.6142	NPC2295
Remote Similarity	0.6142	NPC233926
Remote Similarity	0.6142	NPC477564
Remote Similarity	0.614	NPC70259
Remote Similarity	0.6139	NPC209377
Remote Similarity	0.6133	NPC29477
Remote Similarity	0.6133	NPC217903
Remote Similarity	0.6133	NPC326027
Remote Similarity	0.6133	NPC136112
Remote Similarity	0.6133	NPC141739
Remote Similarity	0.6133	NPC321166
Remote Similarity	0.6125	NPC469722
Remote Similarity	0.6121	NPC289786
Remote Similarity	0.6121	NPC328763
Remote Similarity	0.6121	NPC203972
Remote Similarity	0.6119	NPC52801
Remote Similarity	0.6117	NPC190783
Remote Similarity	0.6117	NPC231163
Remote Similarity	0.6117	NPC318591
Remote Similarity	0.6117	NPC232386
Remote Similarity	0.6117	NPC152680
Remote Similarity	0.6114	NPC249996
Remote Similarity	0.6114	NPC128115
Remote Similarity	0.6111	NPC189266
Remote Similarity	0.6111	NPC2413
Remote Similarity	0.6111	NPC172765
Remote Similarity	0.6111	NPC276588
Remote Similarity	0.6111	NPC278799
Remote Similarity	0.6111	NPC207757
Remote Similarity	0.6111	NPC204828
Remote Similarity	0.6111	NPC193949
Remote Similarity	0.6111	NPC110416
Remote Similarity	0.6111	NPC469817
Remote Similarity	0.6111	NPC5238
Remote Similarity	0.6111	NPC54379
Remote Similarity	0.6111	NPC39701
Remote Similarity	0.6111	NPC127674
Remote Similarity	0.6111	NPC184026
Remote Similarity	0.6111	NPC249797
Remote Similarity	0.6111	NPC295691
Remote Similarity	0.6111	NPC255253
Remote Similarity	0.6108	NPC56887
Remote Similarity	0.6108	NPC193853
Remote Similarity	0.6108	NPC223077
Remote Similarity	0.6106	NPC66191
Remote Similarity	0.6106	NPC316297
Remote Similarity	0.6106	NPC260118
Remote Similarity	0.6106	NPC314817
Remote Similarity	0.6103	NPC82457
Remote Similarity	0.6103	NPC207824
Remote Similarity	0.6103	NPC477565
Remote Similarity	0.6103	NPC48490
Remote Similarity	0.6103	NPC103379
Remote Similarity	0.6103	NPC274661
Remote Similarity	0.6103	NPC60538
Remote Similarity	0.6103	NPC175890
Remote Similarity	0.6103	NPC11296
Remote Similarity	0.6102	NPC43275
Remote Similarity	0.61	NPC221864
Remote Similarity	0.61	NPC57105
Remote Similarity	0.61	NPC177404

Drug Structure

NPD5652 OpenBabel08211708292D 35 37 0 0 1 0 0 0 0 0999 V2000 -1.7321 -1.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 -0.8660 1.5000 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 -0.0000 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 -4.3301 0.5000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 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 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 31 1 0 0 0 0 3 9 1 0 0 0 0 3 11 1 0 0 0 0 4 6 1 0 0 0 0 4 15 2 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 20 1 0 0 0 0 9 28 1 0 0 0 0 10 28 1 0 0 0 0 11 32 1 0 0 0 0 12 17 1 0 0 0 0 12 18 2 0 0 0 0 13 19 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 14 28 1 0 0 0 0 15 25 1 0 0 0 0 16 32 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 20 22 1 0 0 0 0 20 27 1 6 0 0 0 21 30 1 0 0 0 0 22 31 1 6 0 0 0 23 27 2 3 0 0 0 23 29 1 0 0 0 0 26 33 1 0 0 0 0 26 34 1 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000222
DrugBank	DB00604
ChEMBL	CHEMBL560739
IUPHAR/BPS
PharmaGKB	PA449011
KEGG Drug	D00274
PubChem CID
ChEBI	3720
CAS Number	81098-60-4

Drug Properties

Molecular Weight	465.18
ALogP	-0.5945
MLogP	3
XLogP	3.273
HDA	5
HBD	2
Rotatable Bonds	15
TPSA	89.54
RO5 Violation	0