NPASS drugs

Drug Information

Drug ID:	NPD4154
Drug Name:	Cilostazol
Molecular Formula:	C20H27N5O2
Canonical SMILES:	O=C1CCc2c(N1)ccc(c2)OCCCCc1nnnn1C1CCCCC1
Standard InCHI:	InChI=1S/C20H27N5O2/c26-20-12-9-15-14-17(10-11-18(15)21-20)27-13-5-4-8-19-22-23-24-25(19)16-6-2-1-3-7-16/h10-11,14,16H,1-9,12-13H2,(H,21,26)
Standard InCHIKey:	RRGUKTPIGVIEKM-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD4154

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	337
0.1-0.2	2154
0.2-0.3	10077
0.3-0.4	3081
0.4-0.5	11556
0.5-0.6	3091
0.6-0.7	586
0.7-0.8	8
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	0.7366	NPC198401
Intermediate Similarity	0.7265	NPC157931
Intermediate Similarity	0.7227	NPC472099
Intermediate Similarity	0.7209	NPC471304
Intermediate Similarity	0.7143	NPC472098
Intermediate Similarity	0.7059	NPC96321
Intermediate Similarity	0.7028	NPC138830
Intermediate Similarity	0.7004	NPC311906
Remote Similarity	0.699	NPC21425
Remote Similarity	0.6959	NPC476465
Remote Similarity	0.6952	NPC230313
Remote Similarity	0.6937	NPC305984
Remote Similarity	0.693	NPC473460
Remote Similarity	0.69	NPC85482
Remote Similarity	0.6886	NPC257851
Remote Similarity	0.688	NPC475816
Remote Similarity	0.6856	NPC471762
Remote Similarity	0.6854	NPC100863
Remote Similarity	0.6816	NPC148183
Remote Similarity	0.6816	NPC152768
Remote Similarity	0.6812	NPC478078
Remote Similarity	0.6812	NPC473007
Remote Similarity	0.6792	NPC243626
Remote Similarity	0.6791	NPC329793
Remote Similarity	0.6789	NPC45190
Remote Similarity	0.6767	NPC475720
Remote Similarity	0.6767	NPC474192
Remote Similarity	0.6757	NPC264176
Remote Similarity	0.674	NPC280799
Remote Similarity	0.6715	NPC176127
Remote Similarity	0.6712	NPC477161
Remote Similarity	0.6712	NPC300156
Remote Similarity	0.671	NPC66777
Remote Similarity	0.6698	NPC473004
Remote Similarity	0.6697	NPC475133
Remote Similarity	0.6682	NPC76748
Remote Similarity	0.6682	NPC478075
Remote Similarity	0.6682	NPC473008
Remote Similarity	0.6682	NPC473569
Remote Similarity	0.6681	NPC303658
Remote Similarity	0.6681	NPC473041
Remote Similarity	0.6667	NPC307963
Remote Similarity	0.6651	NPC92111
Remote Similarity	0.6636	NPC472111
Remote Similarity	0.6636	NPC67904
Remote Similarity	0.6635	NPC296527
Remote Similarity	0.6633	NPC93653
Remote Similarity	0.6622	NPC16066
Remote Similarity	0.6621	NPC207971
Remote Similarity	0.662	NPC204970
Remote Similarity	0.662	NPC71124
Remote Similarity	0.6618	NPC70092
Remote Similarity	0.6612	NPC303374
Remote Similarity	0.6611	NPC295452
Remote Similarity	0.6611	NPC171393
Remote Similarity	0.6607	NPC159815
Remote Similarity	0.6607	NPC10732
Remote Similarity	0.6606	NPC53344
Remote Similarity	0.6606	NPC270918
Remote Similarity	0.6604	NPC45389
Remote Similarity	0.6604	NPC474059
Remote Similarity	0.6604	NPC5630
Remote Similarity	0.66	NPC230942
Remote Similarity	0.66	NPC315498
Remote Similarity	0.6595	NPC187145
Remote Similarity	0.6593	NPC469928
Remote Similarity	0.6591	NPC268077
Remote Similarity	0.6591	NPC475147
Remote Similarity	0.659	NPC5374
Remote Similarity	0.6582	NPC184680
Remote Similarity	0.658	NPC146370
Remote Similarity	0.658	NPC21638
Remote Similarity	0.6579	NPC308906
Remote Similarity	0.6578	NPC473006
Remote Similarity	0.6577	NPC82548
Remote Similarity	0.6573	NPC22476
Remote Similarity	0.6569	NPC477066
Remote Similarity	0.6567	NPC315822
Remote Similarity	0.6564	NPC471197
Remote Similarity	0.6564	NPC313327
Remote Similarity	0.6562	NPC208284
Remote Similarity	0.6562	NPC242923
Remote Similarity	0.656	NPC176538
Remote Similarity	0.6556	NPC228206
Remote Similarity	0.6555	NPC470784
Remote Similarity	0.6555	NPC470785
Remote Similarity	0.655	NPC323969
Remote Similarity	0.6547	NPC477160
Remote Similarity	0.6547	NPC471561
Remote Similarity	0.6545	NPC476098
Remote Similarity	0.6545	NPC41216
Remote Similarity	0.6545	NPC162484
Remote Similarity	0.6545	NPC223427
Remote Similarity	0.6542	NPC477067
Remote Similarity	0.6542	NPC478082
Remote Similarity	0.6542	NPC478081
Remote Similarity	0.6542	NPC473540
Remote Similarity	0.6537	NPC130570
Remote Similarity	0.6535	NPC70172
Remote Similarity	0.6535	NPC471198
Remote Similarity	0.6532	NPC321428
Remote Similarity	0.6528	NPC251090
Remote Similarity	0.6527	NPC471614
Remote Similarity	0.6522	NPC99724
Remote Similarity	0.6516	NPC14339
Remote Similarity	0.6516	NPC473422
Remote Similarity	0.6512	NPC254957
Remote Similarity	0.6512	NPC203972
Remote Similarity	0.6504	NPC478074
Remote Similarity	0.6504	NPC329982
Remote Similarity	0.65	NPC473005
Remote Similarity	0.6498	NPC39370
Remote Similarity	0.6494	NPC148124
Remote Similarity	0.649	NPC56271
Remote Similarity	0.6489	NPC82541
Remote Similarity	0.6484	NPC329747
Remote Similarity	0.6484	NPC315957
Remote Similarity	0.6483	NPC473186
Remote Similarity	0.6482	NPC315257
Remote Similarity	0.6478	NPC476069
Remote Similarity	0.6476	NPC314659
Remote Similarity	0.6468	NPC112937
Remote Similarity	0.6463	NPC46561
Remote Similarity	0.6463	NPC77777
Remote Similarity	0.645	NPC198503
Remote Similarity	0.645	NPC60621
Remote Similarity	0.6449	NPC283207
Remote Similarity	0.6447	NPC62995
Remote Similarity	0.6444	NPC269449
Remote Similarity	0.6444	NPC269367
Remote Similarity	0.6434	NPC17437
Remote Similarity	0.6429	NPC270301
Remote Similarity	0.6429	NPC197335
Remote Similarity	0.6426	NPC194740
Remote Similarity	0.6419	NPC195636
Remote Similarity	0.6419	NPC28510
Remote Similarity	0.6419	NPC126556
Remote Similarity	0.641	NPC26928
Remote Similarity	0.6409	NPC45459
Remote Similarity	0.6409	NPC127178
Remote Similarity	0.6409	NPC315491
Remote Similarity	0.6407	NPC10653
Remote Similarity	0.6407	NPC318525
Remote Similarity	0.64	NPC478006
Remote Similarity	0.6398	NPC469831
Remote Similarity	0.6389	NPC79213
Remote Similarity	0.6388	NPC119722
Remote Similarity	0.6387	NPC180504
Remote Similarity	0.6384	NPC249583
Remote Similarity	0.6384	NPC243850
Remote Similarity	0.6384	NPC16249
Remote Similarity	0.6383	NPC248903
Remote Similarity	0.6381	NPC283810
Remote Similarity	0.6378	NPC315467
Remote Similarity	0.6376	NPC234772
Remote Similarity	0.6376	NPC194967
Remote Similarity	0.6375	NPC6786
Remote Similarity	0.6372	NPC174629
Remote Similarity	0.6368	NPC125597
Remote Similarity	0.6368	NPC285558
Remote Similarity	0.6368	NPC231924
Remote Similarity	0.6364	NPC219397
Remote Similarity	0.6364	NPC288110
Remote Similarity	0.636	NPC266931
Remote Similarity	0.636	NPC253675
Remote Similarity	0.6356	NPC475910
Remote Similarity	0.6356	NPC285192
Remote Similarity	0.6353	NPC478009
Remote Similarity	0.6353	NPC478010
Remote Similarity	0.6352	NPC280272
Remote Similarity	0.6351	NPC474077
Remote Similarity	0.6349	NPC474183
Remote Similarity	0.6345	NPC478080
Remote Similarity	0.6344	NPC187501
Remote Similarity	0.6339	NPC246140
Remote Similarity	0.6339	NPC195787
Remote Similarity	0.6335	NPC249040
Remote Similarity	0.6335	NPC213308
Remote Similarity	0.6332	NPC13397
Remote Similarity	0.633	NPC276517
Remote Similarity	0.633	NPC131017
Remote Similarity	0.6329	NPC223242
Remote Similarity	0.6327	NPC201697
Remote Similarity	0.632	NPC248601
Remote Similarity	0.6318	NPC329631
Remote Similarity	0.6318	NPC473105
Remote Similarity	0.6318	NPC72211
Remote Similarity	0.6316	NPC94157
Remote Similarity	0.6311	NPC4687
Remote Similarity	0.6309	NPC473317
Remote Similarity	0.6309	NPC128476
Remote Similarity	0.6309	NPC46259
Remote Similarity	0.6305	NPC314882
Remote Similarity	0.6303	NPC5167
Remote Similarity	0.6303	NPC474688
Remote Similarity	0.6295	NPC87714
Remote Similarity	0.6293	NPC298436
Remote Similarity	0.6293	NPC24954
Remote Similarity	0.6291	NPC84478
Remote Similarity	0.6288	NPC74562

Drug Structure

NPD4154 OpenBabel08211704332D 28 31 0 0 0 0 0 0 0 0999 V2000 2.2294 2.0074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4373 1.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2784 2.3164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5352 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3596 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3596 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2256 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2256 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7615 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4935 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3596 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4935 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2256 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0916 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0916 -0.9945 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 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 -5.9576 0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6275 -2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9576 -1.4945 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 17 2 0 0 0 0 11 18 2 0 0 0 0 12 20 1 0 0 0 0 13 27 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 25 1 0 0 0 0 17 27 1 0 0 0 0 18 21 1 0 0 0 0 19 22 2 0 0 0 0 19 25 1 0 0 0 0 20 21 1 0 0 0 0 20 26 2 0 0 0 0 21 28 1 0 0 0 0 22 23 1 0 0 0 0 23 24 2 0 0 0 0 24 25 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000191
DrugBank	DB01166
ChEMBL	CHEMBL799
IUPHAR/BPS	7148
PharmaGKB	PA164746334
KEGG Drug	D01896
PubChem CID	2754
ChEBI	31401
CAS Number	73963-72-1

Drug Properties

Molecular Weight	369.22
ALogP	-3.0213
MLogP	2.89
XLogP	3.796
HDA	6
HBD	1
Rotatable Bonds	7
TPSA	81.93
RO5 Violation	0