NPASS drugs

Drug Information

Drug ID:	NPD4740
Drug Name:	Cinitapride
Molecular Formula:	C21H30N4O4
Canonical SMILES:	CCOc1cc(N)c(cc1C(=NC1CCN(CC1)CC1CCC=CC1)O)N(=O)=O
Standard InCHI:	InChI=1S/C21H30N4O4/c1-2-29-20-13-18(22)19(25(27)28)12-17(20)21(26)23-16-8-10-24(11-9-16)14-15-6-4-3-5-7-15/h3-4,12-13,15-16H,2,5-11,14,22H2,1H3,(H,23,26)
Standard InCHIKey:	ZDLBNXXKDMLZMF-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD4740

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	258
0.1-0.2	2062
0.2-0.3	9928
0.3-0.4	3168
0.4-0.5	11756
0.5-0.6	3374
0.6-0.7	343
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	0.7143	NPC111492
Remote Similarity	0.6986	NPC471561
Remote Similarity	0.6963	NPC310894
Remote Similarity	0.695	NPC28510
Remote Similarity	0.684	NPC471532
Remote Similarity	0.6791	NPC471531
Remote Similarity	0.6746	NPC473460
Remote Similarity	0.6737	NPC72291
Remote Similarity	0.6684	NPC168153
Remote Similarity	0.6667	NPC204179
Remote Similarity	0.6667	NPC225381
Remote Similarity	0.665	NPC473008
Remote Similarity	0.6635	NPC473422
Remote Similarity	0.6631	NPC219383
Remote Similarity	0.662	NPC329329
Remote Similarity	0.662	NPC317709
Remote Similarity	0.6614	NPC315257
Remote Similarity	0.6603	NPC315957
Remote Similarity	0.6601	NPC217294
Remote Similarity	0.6589	NPC168250
Remote Similarity	0.6583	NPC70092
Remote Similarity	0.6569	NPC474059
Remote Similarity	0.6566	NPC283152
Remote Similarity	0.656	NPC470002
Remote Similarity	0.656	NPC470001
Remote Similarity	0.6558	NPC476651
Remote Similarity	0.6552	NPC469830
Remote Similarity	0.655	NPC288305
Remote Similarity	0.6544	NPC478074
Remote Similarity	0.6542	NPC475910
Remote Similarity	0.6538	NPC83289
Remote Similarity	0.6538	NPC314948
Remote Similarity	0.6538	NPC189724
Remote Similarity	0.6538	NPC212850
Remote Similarity	0.651	NPC306366
Remote Similarity	0.6505	NPC245974
Remote Similarity	0.6493	NPC214368
Remote Similarity	0.6488	NPC174629
Remote Similarity	0.6486	NPC247298
Remote Similarity	0.6473	NPC203972
Remote Similarity	0.6471	NPC66083
Remote Similarity	0.6471	NPC108826
Remote Similarity	0.6462	NPC19555
Remote Similarity	0.6462	NPC311357
Remote Similarity	0.6459	NPC478049
Remote Similarity	0.6459	NPC472191
Remote Similarity	0.6453	NPC473007
Remote Similarity	0.6449	NPC472111
Remote Similarity	0.6442	NPC230313
Remote Similarity	0.6436	NPC98197
Remote Similarity	0.6425	NPC274732
Remote Similarity	0.6425	NPC231862
Remote Similarity	0.6425	NPC204970
Remote Similarity	0.6422	NPC48353
Remote Similarity	0.6418	NPC283999
Remote Similarity	0.64	NPC127082
Remote Similarity	0.6393	NPC471080
Remote Similarity	0.6393	NPC469592
Remote Similarity	0.6381	NPC272706
Remote Similarity	0.6373	NPC291359
Remote Similarity	0.6368	NPC329747
Remote Similarity	0.6368	NPC184161
Remote Similarity	0.6364	NPC66191
Remote Similarity	0.6364	NPC316297
Remote Similarity	0.6364	NPC314817
Remote Similarity	0.6359	NPC110741
Remote Similarity	0.6359	NPC314113
Remote Similarity	0.6355	NPC469831
Remote Similarity	0.6354	NPC10730
Remote Similarity	0.6354	NPC10875
Remote Similarity	0.6351	NPC469594
Remote Similarity	0.635	NPC288943
Remote Similarity	0.635	NPC473432
Remote Similarity	0.6346	NPC473004
Remote Similarity	0.6343	NPC193777
Remote Similarity	0.6338	NPC232600
Remote Similarity	0.6335	NPC152768
Remote Similarity	0.6335	NPC148183
Remote Similarity	0.6333	NPC471953
Remote Similarity	0.6324	NPC62069
Remote Similarity	0.6318	NPC9475
Remote Similarity	0.6308	NPC475085
Remote Similarity	0.6308	NPC57105
Remote Similarity	0.6308	NPC291535
Remote Similarity	0.6308	NPC475112
Remote Similarity	0.6308	NPC177404
Remote Similarity	0.6308	NPC474077
Remote Similarity	0.6305	NPC470474
Remote Similarity	0.6296	NPC476106
Remote Similarity	0.6294	NPC314861
Remote Similarity	0.6291	NPC329793
Remote Similarity	0.6291	NPC127178
Remote Similarity	0.6286	NPC243626
Remote Similarity	0.6284	NPC469589
Remote Similarity	0.6284	NPC477160
Remote Similarity	0.628	NPC477186
Remote Similarity	0.6279	NPC162484
Remote Similarity	0.6262	NPC276674
Remote Similarity	0.6262	NPC33902
Remote Similarity	0.6262	NPC472329
Remote Similarity	0.6262	NPC472330
Remote Similarity	0.625	NPC283207
Remote Similarity	0.625	NPC470484
Remote Similarity	0.625	NPC14339
Remote Similarity	0.6245	NPC252251
Remote Similarity	0.6244	NPC70172
Remote Similarity	0.6244	NPC254700
Remote Similarity	0.6239	NPC470931
Remote Similarity	0.6238	NPC289786
Remote Similarity	0.6233	NPC52801
Remote Similarity	0.6232	NPC232872
Remote Similarity	0.6231	NPC257354
Remote Similarity	0.623	NPC40209
Remote Similarity	0.623	NPC159589
Remote Similarity	0.6226	NPC70956
Remote Similarity	0.6226	NPC243834
Remote Similarity	0.6225	NPC260118
Remote Similarity	0.6225	NPC118776
Remote Similarity	0.6224	NPC289776
Remote Similarity	0.6224	NPC191863
Remote Similarity	0.6224	NPC133470
Remote Similarity	0.6222	NPC128115
Remote Similarity	0.6217	NPC469792
Remote Similarity	0.6214	NPC313886
Remote Similarity	0.621	NPC201697
Remote Similarity	0.6209	NPC85381
Remote Similarity	0.6205	NPC29647
Remote Similarity	0.6202	NPC320088
Remote Similarity	0.6199	NPC222982
Remote Similarity	0.6197	NPC72211
Remote Similarity	0.6195	NPC215747
Remote Similarity	0.6195	NPC192939
Remote Similarity	0.6193	NPC292143
Remote Similarity	0.6193	NPC139506
Remote Similarity	0.619	NPC477531
Remote Similarity	0.6186	NPC470586
Remote Similarity	0.6182	NPC269449
Remote Similarity	0.6176	NPC265383
Remote Similarity	0.6173	NPC285635
Remote Similarity	0.6173	NPC79328
Remote Similarity	0.6169	NPC83198
Remote Similarity	0.6169	NPC204908
Remote Similarity	0.6166	NPC123011
Remote Similarity	0.6166	NPC256689
Remote Similarity	0.6165	NPC469829
Remote Similarity	0.6161	NPC79293
Remote Similarity	0.6161	NPC279401
Remote Similarity	0.6158	NPC285941
Remote Similarity	0.6154	NPC21425
Remote Similarity	0.6154	NPC219170
Remote Similarity	0.6154	NPC180253
Remote Similarity	0.615	NPC195392
Remote Similarity	0.615	NPC474188
Remote Similarity	0.615	NPC234318
Remote Similarity	0.6147	NPC209174
Remote Similarity	0.6143	NPC469390
Remote Similarity	0.6143	NPC475411
Remote Similarity	0.614	NPC249040
Remote Similarity	0.6136	NPC475133
Remote Similarity	0.6135	NPC28425
Remote Similarity	0.6135	NPC276060
Remote Similarity	0.6132	NPC471113
Remote Similarity	0.6131	NPC127362
Remote Similarity	0.613	NPC110151
Remote Similarity	0.6129	NPC159101
Remote Similarity	0.6129	NPC223427
Remote Similarity	0.6126	NPC119722
Remote Similarity	0.6126	NPC476151
Remote Similarity	0.6123	NPC477532
Remote Similarity	0.6123	NPC310118
Remote Similarity	0.6121	NPC100863
Remote Similarity	0.6119	NPC83241
Remote Similarity	0.6119	NPC198160
Remote Similarity	0.6117	NPC311936
Remote Similarity	0.6114	NPC318805
Remote Similarity	0.6114	NPC41122
Remote Similarity	0.6109	NPC471304
Remote Similarity	0.6108	NPC10871
Remote Similarity	0.6108	NPC166667
Remote Similarity	0.6106	NPC61350
Remote Similarity	0.6106	NPC37957
Remote Similarity	0.6103	NPC2295
Remote Similarity	0.6103	NPC477564
Remote Similarity	0.6103	NPC70259
Remote Similarity	0.6103	NPC303214
Remote Similarity	0.6101	NPC264166
Remote Similarity	0.6101	NPC274291
Remote Similarity	0.6101	NPC87714
Remote Similarity	0.6101	NPC118832
Remote Similarity	0.6101	NPC329708
Remote Similarity	0.6101	NPC47059
Remote Similarity	0.6101	NPC165349
Remote Similarity	0.61	NPC209377
Remote Similarity	0.6099	NPC313466
Remote Similarity	0.6096	NPC477838
Remote Similarity	0.6096	NPC477837
Remote Similarity	0.6091	NPC475326
Remote Similarity	0.6089	NPC66573
Remote Similarity	0.6087	NPC317872
Remote Similarity	0.6087	NPC119579

Drug Structure

NPD4740 OpenBabel08211705272D 32 34 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 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 9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 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 8.6603 2.0000 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 0.8660 0.5000 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 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 3 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 -0.0000 -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 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 N 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 -0.8660 0.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 -1.7321 -1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 29 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 15 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 24 1 0 0 0 0 11 24 1 0 0 0 0 12 17 1 0 0 0 0 12 19 2 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 16 23 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 25 1 0 0 0 0 20 29 1 0 0 0 0 21 23 2 3 0 0 0 21 26 1 0 0 0 0 22 30 1 0 0 0 0 22 31 1 0 0 0 0 25 27 2 0 0 0 0 25 28 2 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNCL003518
DrugBank	DB08810
ChEMBL	CHEMBL2104523
IUPHAR/BPS
PharmaGKB	PA165958427
KEGG Drug	D07700
PubChem CID	68867
ChEBI	135642
CAS Number	66564-14-5

Drug Properties

Molecular Weight	402.23
ALogP	0.072
MLogP	2.89
XLogP	4.326
HDA	4
HBD	2
Rotatable Bonds	11
TPSA	114.22
RO5 Violation	0