NPASS drugs

Drug Information

Drug ID:	NPD3387
Drug Name:	Phenylbutazone
Molecular Formula:	C19H20N2O2
Canonical SMILES:	CCCCC1C(=O)N(N(C1=O)c1ccccc1)c1ccccc1
Standard InCHI:	InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3
Standard InCHIKey:	VYMDGNCVAMGZFE-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD3387

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	120
0.1-0.2	1874
0.2-0.3	9923
0.3-0.4	14002
0.4-0.5	3737
0.5-0.6	1091
0.6-0.7	136
0.7-0.8	6
0.8-0.85	1
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	0.8077	NPC204156
Intermediate Similarity	0.7679	NPC326792
Intermediate Similarity	0.7436	NPC20322
Intermediate Similarity	0.7434	NPC75496
Intermediate Similarity	0.7045	NPC209389
Intermediate Similarity	0.7009	NPC291610
Intermediate Similarity	0.7008	NPC226143
Remote Similarity	0.6984	NPC31651
Remote Similarity	0.6934	NPC471123
Remote Similarity	0.6923	NPC254698
Remote Similarity	0.6912	NPC162417
Remote Similarity	0.6912	NPC316104
Remote Similarity	0.6906	NPC130251
Remote Similarity	0.6906	NPC207554
Remote Similarity	0.6899	NPC257490
Remote Similarity	0.6875	NPC291962
Remote Similarity	0.6875	NPC177684
Remote Similarity	0.6866	NPC187231
Remote Similarity	0.6857	NPC301760
Remote Similarity	0.6846	NPC39818
Remote Similarity	0.6835	NPC469560
Remote Similarity	0.6835	NPC83214
Remote Similarity	0.6822	NPC279385
Remote Similarity	0.6822	NPC179605
Remote Similarity	0.6822	NPC161956
Remote Similarity	0.6822	NPC258531
Remote Similarity	0.6822	NPC112373
Remote Similarity	0.6769	NPC103292
Remote Similarity	0.6739	NPC300299
Remote Similarity	0.6727	NPC229477
Remote Similarity	0.6667	NPC315051
Remote Similarity	0.662	NPC471164
Remote Similarity	0.662	NPC186284
Remote Similarity	0.662	NPC22082
Remote Similarity	0.6617	NPC192533
Remote Similarity	0.6591	NPC268534
Remote Similarity	0.6556	NPC477887
Remote Similarity	0.6554	NPC66936
Remote Similarity	0.6535	NPC57051
Remote Similarity	0.6528	NPC469537
Remote Similarity	0.6522	NPC207428
Remote Similarity	0.6503	NPC470301
Remote Similarity	0.6467	NPC295021
Remote Similarity	0.6447	NPC113946
Remote Similarity	0.6444	NPC470343
Remote Similarity	0.6444	NPC472244
Remote Similarity	0.6443	NPC154602
Remote Similarity	0.6443	NPC243756
Remote Similarity	0.6423	NPC150863
Remote Similarity	0.6412	NPC228515
Remote Similarity	0.64	NPC122106
Remote Similarity	0.64	NPC117032
Remote Similarity	0.64	NPC285381
Remote Similarity	0.6389	NPC2823
Remote Similarity	0.6389	NPC471574
Remote Similarity	0.6377	NPC280807
Remote Similarity	0.6377	NPC314431
Remote Similarity	0.6377	NPC472245
Remote Similarity	0.6376	NPC473329
Remote Similarity	0.6371	NPC473498
Remote Similarity	0.6369	NPC475248
Remote Similarity	0.6369	NPC63047
Remote Similarity	0.6364	NPC472102
Remote Similarity	0.6364	NPC309531
Remote Similarity	0.6364	NPC225319
Remote Similarity	0.635	NPC476950
Remote Similarity	0.634	NPC104345
Remote Similarity	0.634	NPC222029
Remote Similarity	0.6336	NPC192209
Remote Similarity	0.6323	NPC472120
Remote Similarity	0.6323	NPC472101
Remote Similarity	0.6323	NPC472117
Remote Similarity	0.6299	NPC276085
Remote Similarity	0.6294	NPC122553
Remote Similarity	0.629	NPC473418
Remote Similarity	0.6286	NPC53044
Remote Similarity	0.6279	NPC296163
Remote Similarity	0.6275	NPC29285
Remote Similarity	0.6269	NPC475915
Remote Similarity	0.6259	NPC136002
Remote Similarity	0.6258	NPC201424
Remote Similarity	0.625	NPC134825
Remote Similarity	0.6242	NPC472106
Remote Similarity	0.6224	NPC267508
Remote Similarity	0.6216	NPC307456
Remote Similarity	0.6203	NPC214960
Remote Similarity	0.6203	NPC279527
Remote Similarity	0.62	NPC300596
Remote Similarity	0.62	NPC237649
Remote Similarity	0.6194	NPC316582
Remote Similarity	0.619	NPC79618
Remote Similarity	0.619	NPC308197
Remote Similarity	0.619	NPC172170
Remote Similarity	0.619	NPC434
Remote Similarity	0.6188	NPC355
Remote Similarity	0.6183	NPC288232
Remote Similarity	0.6159	NPC322433
Remote Similarity	0.6159	NPC250476
Remote Similarity	0.6154	NPC78154
Remote Similarity	0.6154	NPC143457
Remote Similarity	0.6154	NPC187036
Remote Similarity	0.6154	NPC92689
Remote Similarity	0.6144	NPC478076
Remote Similarity	0.6142	NPC302790
Remote Similarity	0.6138	NPC65408
Remote Similarity	0.6135	NPC474081
Remote Similarity	0.6133	NPC212799
Remote Similarity	0.6129	NPC474430
Remote Similarity	0.6122	NPC238499
Remote Similarity	0.6115	NPC286871
Remote Similarity	0.6115	NPC282339
Remote Similarity	0.6115	NPC469741
Remote Similarity	0.6115	NPC176983
Remote Similarity	0.6115	NPC99632
Remote Similarity	0.6111	NPC325599
Remote Similarity	0.6106	NPC15839
Remote Similarity	0.6099	NPC231382
Remote Similarity	0.6093	NPC242000
Remote Similarity	0.6093	NPC109787
Remote Similarity	0.609	NPC471122
Remote Similarity	0.609	NPC313449
Remote Similarity	0.6087	NPC474926
Remote Similarity	0.6081	NPC277157
Remote Similarity	0.608	NPC275467
Remote Similarity	0.6074	NPC475607
Remote Similarity	0.6069	NPC287358
Remote Similarity	0.6067	NPC324445
Remote Similarity	0.6065	NPC469536
Remote Similarity	0.6063	NPC55529
Remote Similarity	0.6061	NPC286994
Remote Similarity	0.6051	NPC315368
Remote Similarity	0.6049	NPC177261
Remote Similarity	0.6049	NPC96901
Remote Similarity	0.6045	NPC220698
Remote Similarity	0.604	NPC470822
Remote Similarity	0.6039	NPC200743
Remote Similarity	0.6028	NPC194562
Remote Similarity	0.6017	NPC191444
Remote Similarity	0.6016	NPC164802
Remote Similarity	0.6013	NPC194881
Remote Similarity	0.6012	NPC475594
Remote Similarity	0.6	NPC475761
Remote Similarity	0.6	NPC145754
Remote Similarity	0.5987	NPC36495
Remote Similarity	0.5987	NPC193410
Remote Similarity	0.5986	NPC242933
Remote Similarity	0.5984	NPC472258
Remote Similarity	0.5984	NPC45033
Remote Similarity	0.5975	NPC328270
Remote Similarity	0.5951	NPC214626
Remote Similarity	0.5951	NPC251212
Remote Similarity	0.5951	NPC139085
Remote Similarity	0.5951	NPC242269
Remote Similarity	0.5949	NPC248117
Remote Similarity	0.5949	NPC68650
Remote Similarity	0.5938	NPC471124
Remote Similarity	0.5938	NPC471130
Remote Similarity	0.5932	NPC176858
Remote Similarity	0.5926	NPC264580
Remote Similarity	0.5926	NPC471943
Remote Similarity	0.5924	NPC61013
Remote Similarity	0.5924	NPC123241
Remote Similarity	0.5921	NPC254798
Remote Similarity	0.5915	NPC470548
Remote Similarity	0.5912	NPC293458
Remote Similarity	0.5912	NPC88970
Remote Similarity	0.5912	NPC476231
Remote Similarity	0.5906	NPC313362
Remote Similarity	0.5904	NPC474041
Remote Similarity	0.5897	NPC262295
Remote Similarity	0.5896	NPC313673
Remote Similarity	0.589	NPC471648
Remote Similarity	0.5887	NPC478079
Remote Similarity	0.5878	NPC472243
Remote Similarity	0.5874	NPC314098
Remote Similarity	0.5868	NPC476483
Remote Similarity	0.5868	NPC11149
Remote Similarity	0.5867	NPC478040
Remote Similarity	0.5864	NPC223595
Remote Similarity	0.5864	NPC224970
Remote Similarity	0.5864	NPC167724
Remote Similarity	0.5862	NPC253476
Remote Similarity	0.586	NPC84317
Remote Similarity	0.5857	NPC79698
Remote Similarity	0.5855	NPC146370
Remote Similarity	0.5855	NPC470440
Remote Similarity	0.5854	NPC285622
Remote Similarity	0.5854	NPC161861
Remote Similarity	0.5849	NPC474058
Remote Similarity	0.5847	NPC297532
Remote Similarity	0.5844	NPC144691
Remote Similarity	0.5833	NPC281094
Remote Similarity	0.5833	NPC473962
Remote Similarity	0.5833	NPC40364
Remote Similarity	0.5828	NPC472118
Remote Similarity	0.5828	NPC469915
Remote Similarity	0.5828	NPC314186
Remote Similarity	0.5827	NPC328877
Remote Similarity	0.5827	NPC38262
Remote Similarity	0.5824	NPC133003

Drug Structure

NPD3387 OpenBabel08211703112D 23 25 0 0 0 0 0 0 0 0999 V2000 1.5942 4.0362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0064 3.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0119 3.3317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6237 -2.9344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3669 -2.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3273 -2.6254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1590 -1.2872 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 -0.5759 2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 0.4067 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 1.5522 2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 14 1 0 0 0 0 4 6 2 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 15 2 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000974
DrugBank	DB00812
ChEMBL	CHEMBL101
IUPHAR/BPS	7270
PharmaGKB	PA450932
KEGG Drug	D00510
PubChem CID	4781
ChEBI	48574
CAS Number	50-33-9

Drug Properties

Molecular Weight	308.15
ALogP	-1.6834
MLogP	3.11
XLogP	5.664
HDA	4
HBD	0
Rotatable Bonds	6
TPSA	40.62
RO5 Violation	1