NPASS drugs

Drug Information

Drug ID:	NPD2151
Drug Name:	Alizapride
Molecular Formula:	C16H21N5O2
Canonical SMILES:	C=CCN1CCCC1CN=C(c1cc2[nH]nnc2cc1OC)O
Standard InCHI:	InChI=1S/C16H21N5O2/c1-3-6-21-7-4-5-11(21)10-17-16(22)12-8-13-14(19-20-18-13)9-15(12)23-2/h3,8-9,11H,1,4-7,10H2,2H3,(H,17,22)(H,18,19,20)
Standard InCHIKey:	KSEYRUGYKHXGFW-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; DrugBank

Structural Similarity Between NPASS Natural Products and NPD2151

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	349
0.1-0.2	2844
0.2-0.3	9802
0.3-0.4	5526
0.4-0.5	9286
0.5-0.6	2671
0.6-0.7	395
0.7-0.8	17
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	0.7299	NPC471080
Intermediate Similarity	0.7299	NPC469592
Intermediate Similarity	0.726	NPC193777
Intermediate Similarity	0.7255	NPC18487
Intermediate Similarity	0.7248	NPC227908
Intermediate Similarity	0.7176	NPC86078
Intermediate Similarity	0.7163	NPC469594
Intermediate Similarity	0.7157	NPC70956
Intermediate Similarity	0.7157	NPC243834
Intermediate Similarity	0.7136	NPC478074
Intermediate Similarity	0.7136	NPC315957
Intermediate Similarity	0.7064	NPC310118
Intermediate Similarity	0.7053	NPC121772
Intermediate Similarity	0.7033	NPC223427
Intermediate Similarity	0.7028	NPC469589
Intermediate Similarity	0.7009	NPC48353
Intermediate Similarity	0.7005	NPC303658
Remote Similarity	0.6982	NPC473185
Remote Similarity	0.6981	NPC475910
Remote Similarity	0.6976	NPC131017
Remote Similarity	0.6951	NPC252251
Remote Similarity	0.693	NPC294620
Remote Similarity	0.6906	NPC110151
Remote Similarity	0.6905	NPC475085
Remote Similarity	0.6905	NPC291535
Remote Similarity	0.6905	NPC475112
Remote Similarity	0.6895	NPC213530
Remote Similarity	0.6895	NPC193267
Remote Similarity	0.689	NPC329747
Remote Similarity	0.6889	NPC477531
Remote Similarity	0.6872	NPC162484
Remote Similarity	0.6866	NPC84478
Remote Similarity	0.686	NPC194967
Remote Similarity	0.686	NPC13880
Remote Similarity	0.6857	NPC232727
Remote Similarity	0.6845	NPC307963
Remote Similarity	0.6844	NPC209174
Remote Similarity	0.6835	NPC148183
Remote Similarity	0.6835	NPC152768
Remote Similarity	0.6835	NPC170114
Remote Similarity	0.6833	NPC477532
Remote Similarity	0.683	NPC187145
Remote Similarity	0.6827	NPC153042
Remote Similarity	0.6818	NPC473179
Remote Similarity	0.6816	NPC176127
Remote Similarity	0.681	NPC176538
Remote Similarity	0.681	NPC329793
Remote Similarity	0.6808	NPC476106
Remote Similarity	0.6808	NPC472111
Remote Similarity	0.6804	NPC305984
Remote Similarity	0.6794	NPC72211
Remote Similarity	0.6791	NPC201697
Remote Similarity	0.6789	NPC470549
Remote Similarity	0.6786	NPC477888
Remote Similarity	0.6779	NPC251090
Remote Similarity	0.6774	NPC316981
Remote Similarity	0.6763	NPC84853
Remote Similarity	0.6748	NPC92111
Remote Similarity	0.6745	NPC199277
Remote Similarity	0.6745	NPC135887
Remote Similarity	0.6739	NPC473183
Remote Similarity	0.6736	NPC285635
Remote Similarity	0.673	NPC249040
Remote Similarity	0.6726	NPC314954
Remote Similarity	0.6726	NPC194740
Remote Similarity	0.6712	NPC132642
Remote Similarity	0.6712	NPC477533
Remote Similarity	0.6699	NPC472193
Remote Similarity	0.6699	NPC76748
Remote Similarity	0.6699	NPC70259
Remote Similarity	0.6682	NPC60621
Remote Similarity	0.6682	NPC123976
Remote Similarity	0.6682	NPC11464
Remote Similarity	0.6682	NPC167860
Remote Similarity	0.6667	NPC94943
Remote Similarity	0.6652	NPC473184
Remote Similarity	0.6652	NPC280272
Remote Similarity	0.6651	NPC19872
Remote Similarity	0.6651	NPC205934
Remote Similarity	0.6651	NPC43787
Remote Similarity	0.665	NPC296527
Remote Similarity	0.665	NPC246700
Remote Similarity	0.6638	NPC470784
Remote Similarity	0.6636	NPC174672
Remote Similarity	0.6633	NPC474409
Remote Similarity	0.6621	NPC94157
Remote Similarity	0.6618	NPC190007
Remote Similarity	0.6617	NPC283152
Remote Similarity	0.6609	NPC473182
Remote Similarity	0.6608	NPC470126
Remote Similarity	0.6606	NPC183407
Remote Similarity	0.6606	NPC471304
Remote Similarity	0.6605	NPC475070
Remote Similarity	0.6604	NPC187558
Remote Similarity	0.6595	NPC184680
Remote Similarity	0.6594	NPC475253
Remote Similarity	0.659	NPC476465
Remote Similarity	0.6588	NPC474188
Remote Similarity	0.6584	NPC72980
Remote Similarity	0.6583	NPC258773
Remote Similarity	0.6579	NPC253580
Remote Similarity	0.6577	NPC304926
Remote Similarity	0.6577	NPC476041
Remote Similarity	0.6575	NPC208284
Remote Similarity	0.657	NPC110741
Remote Similarity	0.6569	NPC212535
Remote Similarity	0.6567	NPC470785
Remote Similarity	0.656	NPC476116
Remote Similarity	0.6552	NPC70092
Remote Similarity	0.6552	NPC295228
Remote Similarity	0.6545	NPC473180
Remote Similarity	0.6542	NPC476044
Remote Similarity	0.6537	NPC62069
Remote Similarity	0.6532	NPC470799
Remote Similarity	0.6532	NPC8022
Remote Similarity	0.6531	NPC177404
Remote Similarity	0.6528	NPC285558
Remote Similarity	0.6524	NPC106937
Remote Similarity	0.6522	NPC66083
Remote Similarity	0.6522	NPC46580
Remote Similarity	0.652	NPC161887
Remote Similarity	0.6516	NPC266931
Remote Similarity	0.6511	NPC477066
Remote Similarity	0.651	NPC219383
Remote Similarity	0.65	NPC310894
Remote Similarity	0.6497	NPC476118
Remote Similarity	0.6494	NPC101543
Remote Similarity	0.6494	NPC469554
Remote Similarity	0.6491	NPC202503
Remote Similarity	0.649	NPC128751
Remote Similarity	0.6489	NPC128115
Remote Similarity	0.6489	NPC150239
Remote Similarity	0.6489	NPC174760
Remote Similarity	0.6488	NPC478080
Remote Similarity	0.6483	NPC477067
Remote Similarity	0.6483	NPC473540
Remote Similarity	0.6483	NPC478082
Remote Similarity	0.6483	NPC478081
Remote Similarity	0.6481	NPC473187
Remote Similarity	0.6476	NPC204970
Remote Similarity	0.6473	NPC314573
Remote Similarity	0.6473	NPC171171
Remote Similarity	0.6473	NPC473041
Remote Similarity	0.6473	NPC96321
Remote Similarity	0.6471	NPC26679
Remote Similarity	0.6471	NPC472098
Remote Similarity	0.6466	NPC180504
Remote Similarity	0.6465	NPC267423
Remote Similarity	0.6462	NPC242209
Remote Similarity	0.6459	NPC106833
Remote Similarity	0.6459	NPC469497
Remote Similarity	0.6455	NPC5145
Remote Similarity	0.6455	NPC199667
Remote Similarity	0.6449	NPC128823
Remote Similarity	0.6439	NPC118776
Remote Similarity	0.6438	NPC470931
Remote Similarity	0.6435	NPC295898
Remote Similarity	0.6432	NPC267928
Remote Similarity	0.6432	NPC162748
Remote Similarity	0.6429	NPC28510
Remote Similarity	0.6425	NPC87413
Remote Similarity	0.6425	NPC314002
Remote Similarity	0.6422	NPC88363
Remote Similarity	0.6417	NPC91868
Remote Similarity	0.6417	NPC63971
Remote Similarity	0.6415	NPC195314
Remote Similarity	0.6409	NPC185782
Remote Similarity	0.6409	NPC473181
Remote Similarity	0.6409	NPC209769
Remote Similarity	0.6409	NPC174758
Remote Similarity	0.6406	NPC475774
Remote Similarity	0.6406	NPC476138
Remote Similarity	0.6406	NPC245816
Remote Similarity	0.6404	NPC288943
Remote Similarity	0.6402	NPC475666
Remote Similarity	0.64	NPC247803
Remote Similarity	0.6398	NPC477861
Remote Similarity	0.6392	NPC36168
Remote Similarity	0.6392	NPC26872
Remote Similarity	0.6391	NPC6215
Remote Similarity	0.6389	NPC470586
Remote Similarity	0.6383	NPC6786
Remote Similarity	0.6381	NPC174629
Remote Similarity	0.6378	NPC469428
Remote Similarity	0.6377	NPC204717
Remote Similarity	0.6376	NPC21638
Remote Similarity	0.6375	NPC17437
Remote Similarity	0.6373	NPC96890
Remote Similarity	0.6368	NPC277351
Remote Similarity	0.6364	NPC82548
Remote Similarity	0.6364	NPC469830
Remote Similarity	0.636	NPC81939
Remote Similarity	0.6359	NPC266551
Remote Similarity	0.6359	NPC219963
Remote Similarity	0.6356	NPC169402
Remote Similarity	0.6356	NPC101350
Remote Similarity	0.6352	NPC475720
Remote Similarity	0.6352	NPC474192
Remote Similarity	0.6347	NPC475841
Remote Similarity	0.6347	NPC474145

Drug Structure

NPD2151 OpenBabel08211701392D 25 27 0 0 1 0 0 0 0 0999 V2000 -5.2962 -3.7450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2473 -4.0540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9516 -0.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9735 -1.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9904 -3.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4516 -1.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 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 -6.7825 -2.4067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 0.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 2 23 1 0 0 0 0 3 6 1 0 0 0 0 4 5 1 0 0 0 0 4 7 1 0 0 0 0 5 11 1 0 0 0 0 6 21 1 0 0 0 0 7 21 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 15 2 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 3 0 0 0 16 22 1 0 0 0 0 18 20 1 0 0 0 0 18 24 1 0 0 0 0 19 20 2 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB000253
DrugBank	DB01425
ChEMBL	CHEMBL290194
IUPHAR/BPS
PharmaGKB	PA164744894
KEGG Drug
PubChem CID
ChEBI	94316
CAS Number	59338-93-1

Drug Properties

Molecular Weight	315.17
ALogP	-0.6489
MLogP	2.45
XLogP	1.969
HDA	6
HBD	2
Rotatable Bonds	8
TPSA	86.63
RO5 Violation	0