NPASS drugs

Drug Information

Drug ID:	NPD1414
Drug Name:	Metoclopramide
Molecular Formula:	C14H22ClN3O2
Canonical SMILES:	CCN(CCN=C(c1cc(Cl)c(cc1OC)N)O)CC
Standard InCHI:	InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)
Standard InCHIKey:	TTWJBBZEZQICBI-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD1414

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	220
0.1-0.2	2604
0.2-0.3	10130
0.3-0.4	3474
0.4-0.5	11742
0.5-0.6	2584
0.6-0.7	134
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	0.7135	NPC232872
Intermediate Similarity	0.7076	NPC219383
Remote Similarity	0.6833	NPC208280
Remote Similarity	0.6778	NPC238430
Remote Similarity	0.6758	NPC310894
Remote Similarity	0.6649	NPC168153
Remote Similarity	0.658	NPC28510
Remote Similarity	0.6562	NPC295287
Remote Similarity	0.6541	NPC225381
Remote Similarity	0.6536	NPC226914
Remote Similarity	0.6524	NPC9475
Remote Similarity	0.6519	NPC72291
Remote Similarity	0.6414	NPC243834
Remote Similarity	0.6414	NPC70956
Remote Similarity	0.6412	NPC166667
Remote Similarity	0.6387	NPC272375
Remote Similarity	0.6375	NPC43275
Remote Similarity	0.6359	NPC174629
Remote Similarity	0.6335	NPC160120
Remote Similarity	0.6335	NPC289330
Remote Similarity	0.6335	NPC471308
Remote Similarity	0.6335	NPC17388
Remote Similarity	0.6335	NPC53596
Remote Similarity	0.6324	NPC19555
Remote Similarity	0.6323	NPC9336
Remote Similarity	0.6321	NPC474498
Remote Similarity	0.6319	NPC291359
Remote Similarity	0.6313	NPC184161
Remote Similarity	0.6306	NPC264782
Remote Similarity	0.6298	NPC10875
Remote Similarity	0.6298	NPC10730
Remote Similarity	0.6296	NPC473432
Remote Similarity	0.6294	NPC204970
Remote Similarity	0.6284	NPC306366
Remote Similarity	0.6279	NPC166655
Remote Similarity	0.627	NPC204179
Remote Similarity	0.6269	NPC62069
Remote Similarity	0.6264	NPC469428
Remote Similarity	0.6263	NPC283152
Remote Similarity	0.625	NPC177404
Remote Similarity	0.6244	NPC274268
Remote Similarity	0.6242	NPC325013
Remote Similarity	0.6226	NPC222982
Remote Similarity	0.6225	NPC473460
Remote Similarity	0.622	NPC471314
Remote Similarity	0.622	NPC471315
Remote Similarity	0.6213	NPC313466
Remote Similarity	0.6198	NPC70092
Remote Similarity	0.6195	NPC473422
Remote Similarity	0.6193	NPC474059
Remote Similarity	0.619	NPC471080
Remote Similarity	0.619	NPC469592
Remote Similarity	0.6186	NPC84478
Remote Similarity	0.6184	NPC475910
Remote Similarity	0.6183	NPC70172
Remote Similarity	0.6176	NPC291535
Remote Similarity	0.6176	NPC475085
Remote Similarity	0.6176	NPC475112
Remote Similarity	0.6173	NPC469830
Remote Similarity	0.6171	NPC301702
Remote Similarity	0.6158	NPC121772
Remote Similarity	0.6135	NPC41801
Remote Similarity	0.6135	NPC193777
Remote Similarity	0.6129	NPC37584
Remote Similarity	0.6126	NPC288943
Remote Similarity	0.6119	NPC13880
Remote Similarity	0.6118	NPC476689
Remote Similarity	0.6118	NPC476685
Remote Similarity	0.6118	NPC476687
Remote Similarity	0.6114	NPC477837
Remote Similarity	0.6114	NPC477838
Remote Similarity	0.6114	NPC314113
Remote Similarity	0.6114	NPC265383
Remote Similarity	0.6114	NPC283999
Remote Similarity	0.6108	NPC29477
Remote Similarity	0.6108	NPC235628
Remote Similarity	0.6099	NPC26872
Remote Similarity	0.6094	NPC127082
Remote Similarity	0.6087	NPC258992
Remote Similarity	0.6087	NPC476106
Remote Similarity	0.6085	NPC269383
Remote Similarity	0.6085	NPC151030
Remote Similarity	0.6085	NPC257354
Remote Similarity	0.6082	NPC260118
Remote Similarity	0.6082	NPC93882
Remote Similarity	0.6082	NPC130595
Remote Similarity	0.6078	NPC315957
Remote Similarity	0.6078	NPC329747
Remote Similarity	0.6077	NPC469589
Remote Similarity	0.6075	NPC191863
Remote Similarity	0.6075	NPC315498
Remote Similarity	0.6075	NPC469594
Remote Similarity	0.6075	NPC289776
Remote Similarity	0.6075	NPC133470
Remote Similarity	0.6075	NPC230942
Remote Similarity	0.6071	NPC42591
Remote Similarity	0.607	NPC131017
Remote Similarity	0.6067	NPC473874
Remote Similarity	0.6059	NPC72211
Remote Similarity	0.6054	NPC29647
Remote Similarity	0.6051	NPC192939
Remote Similarity	0.6051	NPC215747
Remote Similarity	0.6051	NPC311936
Remote Similarity	0.6049	NPC323948
Remote Similarity	0.6049	NPC232600
Remote Similarity	0.6047	NPC285078
Remote Similarity	0.6047	NPC313737
Remote Similarity	0.6047	NPC184437
Remote Similarity	0.6047	NPC6854
Remote Similarity	0.6039	NPC256838
Remote Similarity	0.6034	NPC9373
Remote Similarity	0.6033	NPC315257
Remote Similarity	0.6026	NPC186469
Remote Similarity	0.6025	NPC303370
Remote Similarity	0.6023	NPC212850
Remote Similarity	0.6023	NPC83289
Remote Similarity	0.6023	NPC255550
Remote Similarity	0.6023	NPC308885
Remote Similarity	0.6023	NPC189724
Remote Similarity	0.6022	NPC79328
Remote Similarity	0.602	NPC119579
Remote Similarity	0.6012	NPC5932
Remote Similarity	0.6012	NPC218530
Remote Similarity	0.601	NPC228040
Remote Similarity	0.601	NPC224928
Remote Similarity	0.601	NPC66083
Remote Similarity	0.601	NPC219170
Remote Similarity	0.601	NPC180253
Remote Similarity	0.6	NPC473185
Remote Similarity	0.6	NPC471321
Remote Similarity	0.6	NPC475411
Remote Similarity	0.6	NPC28368
Remote Similarity	0.6	NPC303658
Remote Similarity	0.6	NPC168250
Remote Similarity	0.6	NPC477888
Remote Similarity	0.6	NPC471306
Remote Similarity	0.5991	NPC316981
Remote Similarity	0.5991	NPC300114
Remote Similarity	0.5991	NPC310118
Remote Similarity	0.599	NPC322424
Remote Similarity	0.599	NPC473007
Remote Similarity	0.599	NPC28425
Remote Similarity	0.599	NPC276060
Remote Similarity	0.5988	NPC307123
Remote Similarity	0.5988	NPC247018
Remote Similarity	0.5988	NPC471953
Remote Similarity	0.5988	NPC97870
Remote Similarity	0.5988	NPC274732
Remote Similarity	0.5981	NPC148183
Remote Similarity	0.5981	NPC152768
Remote Similarity	0.598	NPC217294
Remote Similarity	0.5977	NPC159589
Remote Similarity	0.5977	NPC237227
Remote Similarity	0.5975	NPC166837
Remote Similarity	0.5975	NPC21890
Remote Similarity	0.5972	NPC11464
Remote Similarity	0.5971	NPC232727
Remote Similarity	0.597	NPC141915
Remote Similarity	0.597	NPC206109
Remote Similarity	0.597	NPC114335
Remote Similarity	0.597	NPC280964
Remote Similarity	0.597	NPC114039
Remote Similarity	0.5969	NPC471785
Remote Similarity	0.5964	NPC211992
Remote Similarity	0.5962	NPC478074
Remote Similarity	0.5961	NPC70259
Remote Similarity	0.5961	NPC475702
Remote Similarity	0.5961	NPC303214
Remote Similarity	0.5961	NPC194967
Remote Similarity	0.596	NPC33902
Remote Similarity	0.596	NPC61350
Remote Similarity	0.596	NPC276674
Remote Similarity	0.5952	NPC95733
Remote Similarity	0.5952	NPC62101
Remote Similarity	0.5951	NPC18487
Remote Similarity	0.5949	NPC45112
Remote Similarity	0.5949	NPC263507
Remote Similarity	0.5949	NPC271958
Remote Similarity	0.5949	NPC39822
Remote Similarity	0.5949	NPC134413
Remote Similarity	0.5947	NPC49583
Remote Similarity	0.5945	NPC128115
Remote Similarity	0.5943	NPC126637
Remote Similarity	0.5942	NPC311357
Remote Similarity	0.5941	NPC307963
Remote Similarity	0.5941	NPC203972
Remote Similarity	0.5941	NPC153990
Remote Similarity	0.5939	NPC263835
Remote Similarity	0.5939	NPC321133
Remote Similarity	0.5938	NPC49315
Remote Similarity	0.5936	NPC231862
Remote Similarity	0.5935	NPC189661
Remote Similarity	0.5933	NPC472111
Remote Similarity	0.5929	NPC177056
Remote Similarity	0.592	NPC22476
Remote Similarity	0.592	NPC469390
Remote Similarity	0.5918	NPC161887
Remote Similarity	0.5917	NPC141739
Remote Similarity	0.5917	NPC136112
Remote Similarity	0.5915	NPC48353

Drug Structure

NPD1414 OpenBabel08211700192D 23 23 0 0 0 0 0 0 0 0999 V2000 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 -0.8660 0.5000 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 -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 0.0000 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 0.8660 -1.5000 0.0000 Cl 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 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 20 1 0 0 0 0 4 18 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 10 1 0 0 0 0 8 11 2 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 20 1 0 0 0 0 14 17 2 3 0 0 0 14 19 1 0 0 0 0 16 21 1 0 0 0 0 16 22 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000530
DrugBank	DB01233
ChEMBL	CHEMBL86
IUPHAR/BPS	241
PharmaGKB	PA450475
KEGG Drug	D00726
PubChem CID	4168
ChEBI	107736
CAS Number	364-62-5

Drug Properties

Molecular Weight	299.14
ALogP	0.3786
MLogP	2.34
XLogP	1.562
HDA	4
HBD	2
Rotatable Bonds	13
TPSA	71.08
RO5 Violation	0