NPASS drugs

Drug Information

Drug ID:	NPD5587
Drug Name:	Aripiprazole
Molecular Formula:	C23H27Cl2N3O2
Canonical SMILES:	OC1=Nc2c(CC1)ccc(c2)OCCCCN1CCN(CC1)c1cccc(c1Cl)Cl
Standard InCHI:	InChI=1S/C23H27Cl2N3O2/c24-19-4-3-5-21(23(19)25)28-13-11-27(12-14-28)10-1-2-15-30-18-8-6-17-7-9-22(29)26-20(17)16-18/h3-6,8,16H,1-2,7,9-15H2,(H,26,29)
Standard InCHIKey:	CEUORZQYGODEFX-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5587

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	323
0.1-0.2	2384
0.2-0.3	10083
0.3-0.4	3242
0.4-0.5	11409
0.5-0.6	2984
0.6-0.7	463
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	0.7065	NPC315257
Intermediate Similarity	0.7056	NPC232872
Remote Similarity	0.6882	NPC10875
Remote Similarity	0.6882	NPC10730
Remote Similarity	0.6825	NPC469589
Remote Similarity	0.6821	NPC283152
Remote Similarity	0.6769	NPC168153
Remote Similarity	0.6766	NPC477186
Remote Similarity	0.6754	NPC299582
Remote Similarity	0.6746	NPC473460
Remote Similarity	0.6735	NPC127082
Remote Similarity	0.6733	NPC174629
Remote Similarity	0.6698	NPC471080
Remote Similarity	0.6698	NPC469592
Remote Similarity	0.6684	NPC473432
Remote Similarity	0.6684	NPC288943
Remote Similarity	0.6682	NPC472111
Remote Similarity	0.6667	NPC204970
Remote Similarity	0.6651	NPC264176
Remote Similarity	0.665	NPC62069
Remote Similarity	0.6634	NPC66083
Remote Similarity	0.662	NPC475910
Remote Similarity	0.6603	NPC127178
Remote Similarity	0.6591	NPC128115
Remote Similarity	0.6589	NPC471561
Remote Similarity	0.6584	NPC33902
Remote Similarity	0.6584	NPC276674
Remote Similarity	0.658	NPC70172
Remote Similarity	0.658	NPC24954
Remote Similarity	0.6579	NPC26850
Remote Similarity	0.6575	NPC469594
Remote Similarity	0.6573	NPC184437
Remote Similarity	0.6569	NPC473569
Remote Similarity	0.6566	NPC285941
Remote Similarity	0.6557	NPC285558
Remote Similarity	0.6542	NPC470931
Remote Similarity	0.654	NPC15987
Remote Similarity	0.654	NPC52801
Remote Similarity	0.654	NPC295898
Remote Similarity	0.654	NPC311357
Remote Similarity	0.6538	NPC189724
Remote Similarity	0.6538	NPC212850
Remote Similarity	0.6538	NPC83289
Remote Similarity	0.6537	NPC28510
Remote Similarity	0.6524	NPC329747
Remote Similarity	0.6508	NPC26872
Remote Similarity	0.6507	NPC234933
Remote Similarity	0.6505	NPC473004
Remote Similarity	0.6495	NPC198160
Remote Similarity	0.6493	NPC470586
Remote Similarity	0.6486	NPC247298
Remote Similarity	0.6486	NPC329830
Remote Similarity	0.6485	NPC84478
Remote Similarity	0.6479	NPC473422
Remote Similarity	0.6479	NPC14339
Remote Similarity	0.6477	NPC177404
Remote Similarity	0.6471	NPC469830
Remote Similarity	0.6471	NPC193267
Remote Similarity	0.6471	NPC213530
Remote Similarity	0.6462	NPC291535
Remote Similarity	0.6462	NPC475085
Remote Similarity	0.6462	NPC475112
Remote Similarity	0.6456	NPC56271
Remote Similarity	0.6455	NPC184161
Remote Similarity	0.6449	NPC476106
Remote Similarity	0.6439	NPC110741
Remote Similarity	0.6439	NPC320088
Remote Similarity	0.6438	NPC189661
Remote Similarity	0.6435	NPC174758
Remote Similarity	0.6429	NPC72211
Remote Similarity	0.6422	NPC49583
Remote Similarity	0.6417	NPC245974
Remote Similarity	0.6414	NPC477185
Remote Similarity	0.64	NPC477187
Remote Similarity	0.6395	NPC99891
Remote Similarity	0.6394	NPC79293
Remote Similarity	0.6394	NPC279401
Remote Similarity	0.6386	NPC118776
Remote Similarity	0.6386	NPC190461
Remote Similarity	0.6382	NPC312872
Remote Similarity	0.6378	NPC19555
Remote Similarity	0.6377	NPC1820
Remote Similarity	0.6373	NPC473007
Remote Similarity	0.6368	NPC67904
Remote Similarity	0.6368	NPC11017
Remote Similarity	0.6368	NPC219383
Remote Similarity	0.6368	NPC274268
Remote Similarity	0.6364	NPC471604
Remote Similarity	0.6364	NPC230313
Remote Similarity	0.6359	NPC174672
Remote Similarity	0.6359	NPC314113
Remote Similarity	0.6355	NPC223427
Remote Similarity	0.6355	NPC162484
Remote Similarity	0.6355	NPC471785
Remote Similarity	0.6351	NPC303658
Remote Similarity	0.6351	NPC173080
Remote Similarity	0.6347	NPC116178
Remote Similarity	0.6346	NPC280964
Remote Similarity	0.6346	NPC206109
Remote Similarity	0.6346	NPC114039
Remote Similarity	0.6346	NPC114335
Remote Similarity	0.6346	NPC141915
Remote Similarity	0.6341	NPC61350
Remote Similarity	0.634	NPC93653
Remote Similarity	0.6337	NPC287588
Remote Similarity	0.6337	NPC39822
Remote Similarity	0.6335	NPC476568
Remote Similarity	0.6333	NPC70259
Remote Similarity	0.6333	NPC473053
Remote Similarity	0.6332	NPC66573
Remote Similarity	0.633	NPC167860
Remote Similarity	0.633	NPC123976
Remote Similarity	0.633	NPC476651
Remote Similarity	0.6329	NPC474904
Remote Similarity	0.6329	NPC474059
Remote Similarity	0.6327	NPC254700
Remote Similarity	0.6324	NPC179704
Remote Similarity	0.6323	NPC37957
Remote Similarity	0.6318	NPC217903
Remote Similarity	0.6318	NPC321166
Remote Similarity	0.6313	NPC205926
Remote Similarity	0.6311	NPC21425
Remote Similarity	0.631	NPC473874
Remote Similarity	0.6308	NPC191863
Remote Similarity	0.6308	NPC133470
Remote Similarity	0.6308	NPC289776
Remote Similarity	0.6308	NPC230942
Remote Similarity	0.6308	NPC216816
Remote Similarity	0.6308	NPC315498
Remote Similarity	0.6307	NPC325013
Remote Similarity	0.6303	NPC70956
Remote Similarity	0.6303	NPC472191
Remote Similarity	0.6303	NPC243834
Remote Similarity	0.6301	NPC471532
Remote Similarity	0.6301	NPC263835
Remote Similarity	0.6298	NPC22476
Remote Similarity	0.6298	NPC469390
Remote Similarity	0.6295	NPC477533
Remote Similarity	0.6293	NPC249405
Remote Similarity	0.6291	NPC315957
Remote Similarity	0.6289	NPC291359
Remote Similarity	0.6286	NPC471315
Remote Similarity	0.6286	NPC205934
Remote Similarity	0.6286	NPC471314
Remote Similarity	0.6286	NPC43787
Remote Similarity	0.6279	NPC469440
Remote Similarity	0.6279	NPC41216
Remote Similarity	0.6277	NPC185838
Remote Similarity	0.6277	NPC9373
Remote Similarity	0.6274	NPC100863
Remote Similarity	0.6273	NPC112206
Remote Similarity	0.6273	NPC127996
Remote Similarity	0.6273	NPC202605
Remote Similarity	0.6273	NPC48353
Remote Similarity	0.6267	NPC477532
Remote Similarity	0.6267	NPC46259
Remote Similarity	0.6262	NPC232727
Remote Similarity	0.6262	NPC204385
Remote Similarity	0.6262	NPC314573
Remote Similarity	0.6261	NPC274982
Remote Similarity	0.6261	NPC152768
Remote Similarity	0.6261	NPC148183
Remote Similarity	0.6256	NPC162653
Remote Similarity	0.6256	NPC231862
Remote Similarity	0.6256	NPC21638
Remote Similarity	0.6256	NPC70092
Remote Similarity	0.625	NPC17565
Remote Similarity	0.625	NPC264166
Remote Similarity	0.625	NPC329708
Remote Similarity	0.625	NPC16452
Remote Similarity	0.625	NPC165349
Remote Similarity	0.625	NPC274291
Remote Similarity	0.625	NPC118832
Remote Similarity	0.625	NPC47059
Remote Similarity	0.625	NPC473008
Remote Similarity	0.625	NPC476581
Remote Similarity	0.625	NPC87714
Remote Similarity	0.625	NPC36229
Remote Similarity	0.6244	NPC241263
Remote Similarity	0.6239	NPC280272
Remote Similarity	0.6238	NPC471825
Remote Similarity	0.6238	NPC302001
Remote Similarity	0.6237	NPC93593
Remote Similarity	0.6233	NPC288759
Remote Similarity	0.6233	NPC305984
Remote Similarity	0.6231	NPC477888
Remote Similarity	0.6231	NPC257354
Remote Similarity	0.6227	NPC82541
Remote Similarity	0.6226	NPC478049
Remote Similarity	0.6226	NPC161804
Remote Similarity	0.6226	NPC234318
Remote Similarity	0.6226	NPC314948
Remote Similarity	0.6224	NPC57105
Remote Similarity	0.6214	NPC313886
Remote Similarity	0.6214	NPC42591
Remote Similarity	0.6212	NPC314861
Remote Similarity	0.6211	NPC179825
Remote Similarity	0.6211	NPC191376
Remote Similarity	0.6211	NPC476151
Remote Similarity	0.6211	NPC321505

Drug Structure

NPD5587 OpenBabel08211708292D 31 34 0 0 0 0 0 0 0 0999 V2000 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 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 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 -3.0000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 -6.0622 -2.5000 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 -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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -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 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 Cl 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 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 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 1 10 1 0 0 0 0 2 15 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 19 1 0 0 0 0 5 21 2 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 22 1 0 0 0 0 10 27 1 0 0 0 0 11 13 1 0 0 0 0 11 27 1 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 20 2 0 0 0 0 18 30 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 26 1 0 0 0 0 21 23 1 0 0 0 0 21 28 1 0 0 0 0 22 26 2 0 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 29 31 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000076; DNCL003086; DNCL003115
DrugBank	DB01238
ChEMBL	CHEMBL1112
IUPHAR/BPS	34
PharmaGKB	PA10026
KEGG Drug	D01164
PubChem CID	60795
ChEBI	31236
CAS Number	129722-12-9

Drug Properties

Molecular Weight	447.15
ALogP	0.8701
MLogP	3.22
XLogP	4.588
HDA	4
HBD	1
Rotatable Bonds	10
TPSA	48.3
RO5 Violation	0