NPASS drugs

Drug Information

Drug ID:	NPD6536
Drug Name:	Ketoconazole
Molecular Formula:	C26H28Cl2N4O4
Canonical SMILES:	Clc1ccc(c(c1)Cl)C1(OCC(O1)COc1ccc(cc1)N1CCN(CC1)C(=O)C)Cn1cncc1
Standard InCHI:	InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3
Standard InCHIKey:	XMAYWYJOQHXEEK-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; DrugBank; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD6536

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	437
0.1-0.2	3159
0.2-0.3	9673
0.3-0.4	8670
0.4-0.5	6933
0.5-0.6	1871
0.6-0.7	136
0.7-0.8	9
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

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
High Similarity	1.0	NPC471614
Intermediate Similarity	0.8442	NPC228206
Intermediate Similarity	0.7456	NPC242923
Intermediate Similarity	0.7382	NPC308906
Intermediate Similarity	0.7276	NPC477795
Intermediate Similarity	0.7276	NPC477805
Intermediate Similarity	0.7276	NPC477806
Intermediate Similarity	0.7276	NPC477796
Intermediate Similarity	0.7149	NPC12100
Intermediate Similarity	0.7029	NPC17305
Intermediate Similarity	0.7008	NPC160666
Remote Similarity	0.6972	NPC472434
Remote Similarity	0.6872	NPC280638
Remote Similarity	0.6836	NPC56271
Remote Similarity	0.6763	NPC467439
Remote Similarity	0.6743	NPC472436
Remote Similarity	0.6737	NPC287208
Remote Similarity	0.6692	NPC472435
Remote Similarity	0.6667	NPC82548
Remote Similarity	0.6654	NPC99891
Remote Similarity	0.6626	NPC197141
Remote Similarity	0.6614	NPC141053
Remote Similarity	0.656	NPC115595
Remote Similarity	0.6531	NPC250178
Remote Similarity	0.651	NPC30540
Remote Similarity	0.65	NPC174672
Remote Similarity	0.6491	NPC150447
Remote Similarity	0.6463	NPC136924
Remote Similarity	0.6453	NPC267928
Remote Similarity	0.6452	NPC46970
Remote Similarity	0.6432	NPC174758
Remote Similarity	0.6414	NPC323244
Remote Similarity	0.6414	NPC187145
Remote Similarity	0.64	NPC35761
Remote Similarity	0.6395	NPC198673
Remote Similarity	0.6389	NPC237978
Remote Similarity	0.6371	NPC477019
Remote Similarity	0.6356	NPC168911
Remote Similarity	0.6349	NPC135549
Remote Similarity	0.6349	NPC313189
Remote Similarity	0.634	NPC314882
Remote Similarity	0.6336	NPC472068
Remote Similarity	0.6327	NPC476287
Remote Similarity	0.6324	NPC314954
Remote Similarity	0.6314	NPC328924
Remote Similarity	0.6308	NPC295452
Remote Similarity	0.6308	NPC171393
Remote Similarity	0.6303	NPC19872
Remote Similarity	0.6289	NPC220852
Remote Similarity	0.6288	NPC26543
Remote Similarity	0.6288	NPC472066
Remote Similarity	0.6288	NPC472067
Remote Similarity	0.6288	NPC472031
Remote Similarity	0.6287	NPC239954
Remote Similarity	0.6286	NPC171409
Remote Similarity	0.6286	NPC296482
Remote Similarity	0.6286	NPC96405
Remote Similarity	0.6286	NPC202768
Remote Similarity	0.6286	NPC53069
Remote Similarity	0.6285	NPC186351
Remote Similarity	0.6279	NPC285343
Remote Similarity	0.6275	NPC300114
Remote Similarity	0.6275	NPC274982
Remote Similarity	0.6275	NPC288349
Remote Similarity	0.625	NPC469554
Remote Similarity	0.6245	NPC478006
Remote Similarity	0.6234	NPC176538
Remote Similarity	0.6227	NPC315467
Remote Similarity	0.6224	NPC475774
Remote Similarity	0.6222	NPC85482
Remote Similarity	0.6218	NPC127085
Remote Similarity	0.6208	NPC54537
Remote Similarity	0.6204	NPC478010
Remote Similarity	0.6204	NPC478009
Remote Similarity	0.6202	NPC253675
Remote Similarity	0.62	NPC315804
Remote Similarity	0.62	NPC313804
Remote Similarity	0.6167	NPC234197
Remote Similarity	0.616	NPC316756
Remote Similarity	0.6157	NPC476138
Remote Similarity	0.6157	NPC245816
Remote Similarity	0.6154	NPC26679
Remote Similarity	0.6154	NPC177056
Remote Similarity	0.6154	NPC28945
Remote Similarity	0.6154	NPC471603
Remote Similarity	0.6154	NPC472098
Remote Similarity	0.6144	NPC133140
Remote Similarity	0.6144	NPC195268
Remote Similarity	0.6138	NPC113369
Remote Similarity	0.6138	NPC290689
Remote Similarity	0.6133	NPC315822
Remote Similarity	0.6132	NPC264166
Remote Similarity	0.6132	NPC274291
Remote Similarity	0.6132	NPC165349
Remote Similarity	0.6132	NPC118832
Remote Similarity	0.6132	NPC47059
Remote Similarity	0.6132	NPC329708
Remote Similarity	0.6131	NPC314056
Remote Similarity	0.6128	NPC471593
Remote Similarity	0.6125	NPC476582
Remote Similarity	0.6125	NPC4071
Remote Similarity	0.6125	NPC476578
Remote Similarity	0.6124	NPC101543
Remote Similarity	0.6122	NPC39092
Remote Similarity	0.6116	NPC211813
Remote Similarity	0.6116	NPC311357
Remote Similarity	0.6107	NPC472111
Remote Similarity	0.6102	NPC130570
Remote Similarity	0.6098	NPC469589
Remote Similarity	0.6094	NPC20249
Remote Similarity	0.6094	NPC107160
Remote Similarity	0.6093	NPC478012
Remote Similarity	0.6093	NPC478011
Remote Similarity	0.6085	NPC21461
Remote Similarity	0.6083	NPC212213
Remote Similarity	0.6074	NPC303374
Remote Similarity	0.6071	NPC314176
Remote Similarity	0.607	NPC477633
Remote Similarity	0.6066	NPC476581
Remote Similarity	0.6066	NPC36229
Remote Similarity	0.6066	NPC16452
Remote Similarity	0.6065	NPC478013
Remote Similarity	0.6064	NPC149471
Remote Similarity	0.6064	NPC271215
Remote Similarity	0.6057	NPC476465
Remote Similarity	0.6056	NPC238945
Remote Similarity	0.605	NPC84853
Remote Similarity	0.6038	NPC323198
Remote Similarity	0.6038	NPC75179
Remote Similarity	0.6035	NPC476518
Remote Similarity	0.6034	NPC219963
Remote Similarity	0.6032	NPC185782
Remote Similarity	0.6031	NPC157931
Remote Similarity	0.6024	NPC251160
Remote Similarity	0.6009	NPC121658
Remote Similarity	0.6009	NPC14651
Remote Similarity	0.6008	NPC123976
Remote Similarity	0.6008	NPC470586
Remote Similarity	0.6008	NPC46451
Remote Similarity	0.6008	NPC167860
Remote Similarity	0.6008	NPC232727
Remote Similarity	0.6008	NPC5145
Remote Similarity	0.6007	NPC74619
Remote Similarity	0.6	NPC316181
Remote Similarity	0.6	NPC151781
Remote Similarity	0.6	NPC74562
Remote Similarity	0.6	NPC210256
Remote Similarity	0.5992	NPC187558
Remote Similarity	0.5992	NPC295228
Remote Similarity	0.5984	NPC54981
Remote Similarity	0.5984	NPC128115
Remote Similarity	0.5983	NPC226202
Remote Similarity	0.5977	NPC323752
Remote Similarity	0.5977	NPC316224
Remote Similarity	0.5977	NPC180504
Remote Similarity	0.597	NPC184680
Remote Similarity	0.5969	NPC110151
Remote Similarity	0.5969	NPC257851
Remote Similarity	0.5968	NPC100079
Remote Similarity	0.5968	NPC23614
Remote Similarity	0.5967	NPC315957
Remote Similarity	0.5966	NPC92111
Remote Similarity	0.5966	NPC266551
Remote Similarity	0.5966	NPC161887
Remote Similarity	0.5959	NPC200836
Remote Similarity	0.5958	NPC198401
Remote Similarity	0.5956	NPC315498
Remote Similarity	0.5956	NPC230942
Remote Similarity	0.5951	NPC316403
Remote Similarity	0.5949	NPC472289
Remote Similarity	0.5947	NPC470785
Remote Similarity	0.5947	NPC474183
Remote Similarity	0.5945	NPC17565
Remote Similarity	0.5945	NPC168209
Remote Similarity	0.5945	NPC193267
Remote Similarity	0.5945	NPC213530
Remote Similarity	0.5944	NPC188420
Remote Similarity	0.5943	NPC31930
Remote Similarity	0.5936	NPC266931
Remote Similarity	0.5932	NPC204385
Remote Similarity	0.593	NPC24370
Remote Similarity	0.593	NPC319232
Remote Similarity	0.5924	NPC76748
Remote Similarity	0.592	NPC208284
Remote Similarity	0.5919	NPC315257
Remote Similarity	0.5917	NPC307963
Remote Similarity	0.5914	NPC65277
Remote Similarity	0.5913	NPC111624
Remote Similarity	0.5911	NPC474145
Remote Similarity	0.5911	NPC475841
Remote Similarity	0.5911	NPC471736
Remote Similarity	0.5903	NPC254700
Remote Similarity	0.5901	NPC477634
Remote Similarity	0.59	NPC476999
Remote Similarity	0.5898	NPC60621
Remote Similarity	0.5898	NPC310118
Remote Similarity	0.5897	NPC118776
Remote Similarity	0.5897	NPC470474
Remote Similarity	0.5897	NPC206201
Remote Similarity	0.5896	NPC202605

Drug Structure

NPD6536 OpenBabel08211710072D 36 40 0 0 1 0 0 0 0 0999 V2000 -6.1192 -2.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3722 -3.5961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7891 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6551 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9230 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7891 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0224 -2.6592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1217 -3.6569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4924 -2.8797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3871 -1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2532 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5211 -0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3871 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9948 -2.9902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6787 -1.1075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0030 -2.2999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1192 -1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3584 -3.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6551 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9230 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6588 -1.8879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6450 -2.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7082 -4.6984 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.2814 -1.2820 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.0553 -3.2985 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0370 -2.0411 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2532 -0.9122 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5211 0.0878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9852 -0.9122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 2.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 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 19 1 0 0 0 0 2 7 2 0 0 0 0 2 20 1 0 0 0 0 3 5 1 0 0 0 0 3 21 2 0 0 0 0 4 6 2 0 0 0 0 4 21 1 0 0 0 0 5 22 2 0 0 0 0 6 22 1 0 0 0 0 7 24 1 0 0 0 0 8 9 2 0 0 0 0 8 29 1 0 0 0 0 9 30 1 0 0 0 0 10 12 1 0 0 0 0 10 31 1 0 0 0 0 11 13 1 0 0 0 0 11 31 1 0 0 0 0 12 32 1 0 0 0 0 13 32 1 0 0 0 0 14 20 2 0 0 0 0 14 25 1 0 0 0 0 15 23 1 0 0 0 0 15 34 1 0 0 0 0 16 23 1 0 0 0 0 16 35 1 0 0 0 0 17 26 1 0 0 0 0 17 30 1 0 0 0 0 18 29 2 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 19 33 2 0 0 0 0 20 27 1 0 0 0 0 21 32 1 0 0 0 0 22 34 1 0 0 0 0 23 36 1 0 0 0 0 24 25 2 0 0 0 0 24 26 1 0 0 0 0 25 28 1 0 0 0 0 26 35 1 0 0 0 0 26 36 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000630
DrugBank	DB01026
ChEMBL	CHEMBL157101
IUPHAR/BPS	2568
PharmaGKB	PA450146
KEGG Drug	D00351
PubChem CID	3823
ChEBI	48339
CAS Number	65277-42-1

Drug Properties

Molecular Weight	530.15
ALogP	0.4786
MLogP	3.22
XLogP	3.385
HDA	7
HBD	0
Rotatable Bonds	11
TPSA	69.06
RO5 Violation	0