NPASS drugs

Drug Information

Drug ID:	NPD5914
Drug Name:	Iloperidone
Molecular Formula:	C24H27FN2O4
Canonical SMILES:	COc1cc(ccc1OCCCN1CCC(CC1)c1noc2c1ccc(c2)F)C(=O)C
Standard InCHI:	InChI=1S/C24H27FN2O4/c1-16(28)18-4-7-21(23(14-18)29-2)30-13-3-10-27-11-8-17(9-12-27)24-20-6-5-19(25)15-22(20)31-26-24/h4-7,14-15,17H,3,8-13H2,1-2H3
Standard InCHIKey:	XMXHEBAFVSFQEX-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5914

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	313
0.1-0.2	1491
0.2-0.3	5838
0.3-0.4	6596
0.4-0.5	4654
0.5-0.6	10457
0.6-0.7	1525
0.7-0.8	16
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	0.7407	NPC146976
Intermediate Similarity	0.7361	NPC236668
Intermediate Similarity	0.7182	NPC313327
Intermediate Similarity	0.7168	NPC246381
Intermediate Similarity	0.7155	NPC119134
Intermediate Similarity	0.7137	NPC24019
Intermediate Similarity	0.7129	NPC85613
Intermediate Similarity	0.7119	NPC270515
Intermediate Similarity	0.7118	NPC22481
Intermediate Similarity	0.7118	NPC329631
Intermediate Similarity	0.7098	NPC210434
Intermediate Similarity	0.707	NPC268077
Intermediate Similarity	0.7056	NPC153631
Intermediate Similarity	0.7047	NPC58661
Intermediate Similarity	0.7026	NPC189903
Intermediate Similarity	0.7026	NPC182907
Remote Similarity	0.6995	NPC207721
Remote Similarity	0.6987	NPC278525
Remote Similarity	0.6983	NPC108342
Remote Similarity	0.698	NPC303581
Remote Similarity	0.698	NPC67978
Remote Similarity	0.6948	NPC71124
Remote Similarity	0.6944	NPC207971
Remote Similarity	0.6943	NPC478189
Remote Similarity	0.694	NPC90875
Remote Similarity	0.6912	NPC308267
Remote Similarity	0.6901	NPC303374
Remote Similarity	0.6901	NPC470021
Remote Similarity	0.6883	NPC88923
Remote Similarity	0.6883	NPC100734
Remote Similarity	0.6883	NPC315634
Remote Similarity	0.688	NPC470022
Remote Similarity	0.6878	NPC5167
Remote Similarity	0.6875	NPC204385
Remote Similarity	0.6869	NPC193906
Remote Similarity	0.6869	NPC23080
Remote Similarity	0.6867	NPC253675
Remote Similarity	0.6859	NPC469978
Remote Similarity	0.6857	NPC191489
Remote Similarity	0.6853	NPC233334
Remote Similarity	0.6851	NPC166722
Remote Similarity	0.6849	NPC124313
Remote Similarity	0.6847	NPC264176
Remote Similarity	0.6847	NPC312872
Remote Similarity	0.6837	NPC5374
Remote Similarity	0.6835	NPC207283
Remote Similarity	0.6835	NPC84164
Remote Similarity	0.683	NPC470002
Remote Similarity	0.683	NPC470001
Remote Similarity	0.682	NPC107123
Remote Similarity	0.6814	NPC227683
Remote Similarity	0.6812	NPC27887
Remote Similarity	0.6812	NPC471615
Remote Similarity	0.6804	NPC469539
Remote Similarity	0.6804	NPC469540
Remote Similarity	0.6802	NPC295479
Remote Similarity	0.6802	NPC220241
Remote Similarity	0.6796	NPC35680
Remote Similarity	0.6796	NPC283810
Remote Similarity	0.6794	NPC116007
Remote Similarity	0.6793	NPC210296
Remote Similarity	0.6787	NPC471561
Remote Similarity	0.678	NPC329992
Remote Similarity	0.6774	NPC31930
Remote Similarity	0.6774	NPC132385
Remote Similarity	0.6771	NPC116178
Remote Similarity	0.677	NPC87560
Remote Similarity	0.677	NPC195120
Remote Similarity	0.6763	NPC121400
Remote Similarity	0.6761	NPC254957
Remote Similarity	0.6758	NPC36229
Remote Similarity	0.6758	NPC16452
Remote Similarity	0.6758	NPC476581
Remote Similarity	0.6757	NPC470020
Remote Similarity	0.6753	NPC478078
Remote Similarity	0.675	NPC26353
Remote Similarity	0.6741	NPC268223
Remote Similarity	0.6741	NPC321166
Remote Similarity	0.6741	NPC217903
Remote Similarity	0.6738	NPC217176
Remote Similarity	0.6736	NPC15406
Remote Similarity	0.6733	NPC35345
Remote Similarity	0.6726	NPC186569
Remote Similarity	0.6726	NPC61731
Remote Similarity	0.6726	NPC471532
Remote Similarity	0.6724	NPC66777
Remote Similarity	0.6724	NPC471762
Remote Similarity	0.6718	NPC470088
Remote Similarity	0.6716	NPC86469
Remote Similarity	0.6715	NPC222524
Remote Similarity	0.6714	NPC195268
Remote Similarity	0.6714	NPC133140
Remote Similarity	0.6713	NPC17677
Remote Similarity	0.6712	NPC41216
Remote Similarity	0.6711	NPC469439
Remote Similarity	0.6711	NPC148391
Remote Similarity	0.6711	NPC323969
Remote Similarity	0.6708	NPC183537
Remote Similarity	0.6698	NPC470023
Remote Similarity	0.6698	NPC477258
Remote Similarity	0.6697	NPC16249
Remote Similarity	0.6697	NPC308943
Remote Similarity	0.6697	NPC198160
Remote Similarity	0.6696	NPC296482
Remote Similarity	0.6696	NPC53069
Remote Similarity	0.6696	NPC202768
Remote Similarity	0.6695	NPC470017
Remote Similarity	0.6683	NPC476443
Remote Similarity	0.6683	NPC133817
Remote Similarity	0.6683	NPC206201
Remote Similarity	0.6682	NPC163829
Remote Similarity	0.6682	NPC38961
Remote Similarity	0.6681	NPC198503
Remote Similarity	0.6681	NPC13249
Remote Similarity	0.668	NPC284685
Remote Similarity	0.6667	NPC114468
Remote Similarity	0.6667	NPC203373
Remote Similarity	0.6667	NPC318068
Remote Similarity	0.6667	NPC134637
Remote Similarity	0.6667	NPC90185
Remote Similarity	0.6667	NPC153644
Remote Similarity	0.6667	NPC227361
Remote Similarity	0.6667	NPC188400
Remote Similarity	0.6667	NPC124658
Remote Similarity	0.6653	NPC1608
Remote Similarity	0.6651	NPC169387
Remote Similarity	0.6651	NPC477259
Remote Similarity	0.665	NPC93653
Remote Similarity	0.6639	NPC77878
Remote Similarity	0.6638	NPC157983
Remote Similarity	0.6638	NPC472099
Remote Similarity	0.6638	NPC118154
Remote Similarity	0.6638	NPC471004
Remote Similarity	0.6638	NPC476436
Remote Similarity	0.6637	NPC2905
Remote Similarity	0.6637	NPC55470
Remote Similarity	0.6636	NPC234933
Remote Similarity	0.6635	NPC83511
Remote Similarity	0.6634	NPC299582
Remote Similarity	0.6623	NPC322482
Remote Similarity	0.6623	NPC134702
Remote Similarity	0.6623	NPC182853
Remote Similarity	0.6622	NPC472098
Remote Similarity	0.6619	NPC473562
Remote Similarity	0.6618	NPC474858
Remote Similarity	0.6613	NPC129897
Remote Similarity	0.661	NPC172222
Remote Similarity	0.6609	NPC7560
Remote Similarity	0.6609	NPC74575
Remote Similarity	0.6609	NPC157931
Remote Similarity	0.6609	NPC257851
Remote Similarity	0.6609	NPC76478
Remote Similarity	0.6608	NPC471531
Remote Similarity	0.6608	NPC148183
Remote Similarity	0.6608	NPC152768
Remote Similarity	0.6607	NPC124086
Remote Similarity	0.6607	NPC290689
Remote Similarity	0.6607	NPC471304
Remote Similarity	0.6604	NPC214629
Remote Similarity	0.6598	NPC51854
Remote Similarity	0.6596	NPC476999
Remote Similarity	0.6595	NPC21638
Remote Similarity	0.6594	NPC256422
Remote Similarity	0.6593	NPC30749
Remote Similarity	0.6592	NPC100573
Remote Similarity	0.6592	NPC207873
Remote Similarity	0.6589	NPC1820
Remote Similarity	0.6586	NPC473833
Remote Similarity	0.6585	NPC284842
Remote Similarity	0.6582	NPC208898
Remote Similarity	0.6582	NPC34770
Remote Similarity	0.6578	NPC220337
Remote Similarity	0.6575	NPC477019
Remote Similarity	0.6573	NPC474009
Remote Similarity	0.6573	NPC162694
Remote Similarity	0.6573	NPC471650
Remote Similarity	0.6571	NPC473188
Remote Similarity	0.6569	NPC101350
Remote Similarity	0.6568	NPC49547
Remote Similarity	0.6566	NPC119669
Remote Similarity	0.6564	NPC16066
Remote Similarity	0.6562	NPC85661
Remote Similarity	0.6559	NPC478045
Remote Similarity	0.6559	NPC53255
Remote Similarity	0.6559	NPC85879
Remote Similarity	0.6559	NPC475301
Remote Similarity	0.6559	NPC326930
Remote Similarity	0.6557	NPC475566
Remote Similarity	0.6557	NPC9729
Remote Similarity	0.6556	NPC166712
Remote Similarity	0.6552	NPC94842
Remote Similarity	0.6552	NPC122436
Remote Similarity	0.655	NPC60211
Remote Similarity	0.655	NPC473041
Remote Similarity	0.6549	NPC305542
Remote Similarity	0.6549	NPC171409
Remote Similarity	0.6549	NPC112206
Remote Similarity	0.6549	NPC96405
Remote Similarity	0.6549	NPC10732
Remote Similarity	0.6549	NPC202605

Drug Structure

NPD5914 OpenBabel08211708292D 31 34 0 0 0 0 0 0 0 0999 V2000 4.1808 -4.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6449 -1.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -2.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8383 -2.3523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1473 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -1.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -2.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1910 -1.8171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -3.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -2.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8601 -2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -1.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5511 -3.5113 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 1.8364 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -4.1636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7788 -0.6636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 0.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 29 1 0 0 0 0 3 10 1 0 0 0 0 3 13 1 0 0 0 0 4 7 2 0 0 0 0 4 18 1 0 0 0 0 5 6 2 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 27 1 0 0 0 0 11 27 1 0 0 0 0 12 27 1 0 0 0 0 13 30 1 0 0 0 0 14 18 2 0 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 28 2 0 0 0 0 17 24 1 0 0 0 0 19 25 1 0 0 0 0 20 22 2 0 0 0 0 20 24 1 0 0 0 0 21 23 2 0 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 29 1 0 0 0 0 24 26 2 0 0 0 0 26 31 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000843
DrugBank	DB04946
ChEMBL	CHEMBL14376
IUPHAR/BPS	87
PharmaGKB	PA161199368
KEGG Drug	D02666
PubChem CID	71360
ChEBI	65173
CAS Number	133454-47-4

Drug Properties

Molecular Weight	426.20
ALogP	-1.2447
MLogP	3.33
XLogP	4.172
HDA	2
HBD	0
Rotatable Bonds	11
TPSA	64.8
RO5 Violation	0