NPASS drugs

Drug Information

Drug ID:	NPD2036
Drug Name:	Retigabine
Molecular Formula:	C16H18FN3O2
Canonical SMILES:	CCOC(=Nc1ccc(cc1N)NCc1ccc(cc1)F)O
Standard InCHI:	InChI=1S/C16H18FN3O2/c1-2-22-16(21)20-15-8-7-13(9-14(15)18)19-10-11-3-5-12(17)6-4-11/h3-9,19H,2,10,18H2,1H3,(H,20,21)
Standard InCHIKey:	PCOBBVZJEWWZFR-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD2036

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	101
0.1-0.2	1772
0.2-0.3	11076
0.3-0.4	12233
0.4-0.5	4092
0.5-0.6	1517
0.6-0.7	98
0.7-0.8	1
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	0.712	NPC291610
Remote Similarity	0.6897	NPC313352
Remote Similarity	0.6797	NPC474430
Remote Similarity	0.6713	NPC476950
Remote Similarity	0.6692	NPC313362
Remote Similarity	0.6644	NPC476687
Remote Similarity	0.6644	NPC476689
Remote Similarity	0.6644	NPC476685
Remote Similarity	0.6643	NPC475915
Remote Similarity	0.6594	NPC313449
Remote Similarity	0.6544	NPC296163
Remote Similarity	0.6541	NPC302790
Remote Similarity	0.6533	NPC287358
Remote Similarity	0.6516	NPC264589
Remote Similarity	0.6508	NPC108339
Remote Similarity	0.6475	NPC192209
Remote Similarity	0.6475	NPC262295
Remote Similarity	0.6466	NPC79618
Remote Similarity	0.6466	NPC434
Remote Similarity	0.6452	NPC78154
Remote Similarity	0.6446	NPC229477
Remote Similarity	0.6423	NPC187036
Remote Similarity	0.6419	NPC53044
Remote Similarity	0.6417	NPC134825
Remote Similarity	0.6414	NPC252794
Remote Similarity	0.6371	NPC173991
Remote Similarity	0.637	NPC145754
Remote Similarity	0.6364	NPC169016
Remote Similarity	0.6331	NPC288232
Remote Similarity	0.6328	NPC471319
Remote Similarity	0.6328	NPC471320
Remote Similarity	0.6286	NPC313673
Remote Similarity	0.6282	NPC311330
Remote Similarity	0.6268	NPC226143
Remote Similarity	0.625	NPC475763
Remote Similarity	0.6225	NPC316104
Remote Similarity	0.6225	NPC184437
Remote Similarity	0.6225	NPC162417
Remote Similarity	0.6224	NPC279385
Remote Similarity	0.6224	NPC179605
Remote Similarity	0.6216	NPC101372
Remote Similarity	0.6207	NPC328683
Remote Similarity	0.6207	NPC283130
Remote Similarity	0.6197	NPC228515
Remote Similarity	0.6194	NPC2823
Remote Similarity	0.6194	NPC22082
Remote Similarity	0.6194	NPC186284
Remote Similarity	0.619	NPC191444
Remote Similarity	0.619	NPC322433
Remote Similarity	0.6187	NPC314141
Remote Similarity	0.6181	NPC103292
Remote Similarity	0.6178	NPC472103
Remote Similarity	0.6174	NPC472245
Remote Similarity	0.6174	NPC473417
Remote Similarity	0.6164	NPC192533
Remote Similarity	0.6144	NPC475707
Remote Similarity	0.6142	NPC245259
Remote Similarity	0.6135	NPC470507
Remote Similarity	0.6124	NPC329430
Remote Similarity	0.6111	NPC176858
Remote Similarity	0.6111	NPC316582
Remote Similarity	0.6108	NPC476118
Remote Similarity	0.6108	NPC311276
Remote Similarity	0.6107	NPC209389
Remote Similarity	0.6107	NPC150863
Remote Similarity	0.6101	NPC314372
Remote Similarity	0.6087	NPC37548
Remote Similarity	0.6087	NPC473329
Remote Similarity	0.6076	NPC190296
Remote Similarity	0.6071	NPC57051
Remote Similarity	0.6069	NPC257490
Remote Similarity	0.6061	NPC469762
Remote Similarity	0.6058	NPC164802
Remote Similarity	0.6051	NPC472241
Remote Similarity	0.6049	NPC105818
Remote Similarity	0.6049	NPC314223
Remote Similarity	0.6049	NPC24678
Remote Similarity	0.6042	NPC291962
Remote Similarity	0.6042	NPC177684
Remote Similarity	0.604	NPC478079
Remote Similarity	0.604	NPC469949
Remote Similarity	0.6039	NPC325599
Remote Similarity	0.6038	NPC242556
Remote Similarity	0.6027	NPC268534
Remote Similarity	0.6026	NPC130251
Remote Similarity	0.6023	NPC318183
Remote Similarity	0.6023	NPC292265
Remote Similarity	0.6016	NPC119677
Remote Similarity	0.6014	NPC472244
Remote Similarity	0.6014	NPC470343
Remote Similarity	0.6013	NPC253476
Remote Similarity	0.6	NPC469785
Remote Similarity	0.6	NPC12857
Remote Similarity	0.6	NPC112373
Remote Similarity	0.6	NPC258531
Remote Similarity	0.6	NPC325252
Remote Similarity	0.6	NPC161956
Remote Similarity	0.6	NPC172937
Remote Similarity	0.6	NPC94167
Remote Similarity	0.5988	NPC68650
Remote Similarity	0.5988	NPC309531
Remote Similarity	0.5988	NPC472102
Remote Similarity	0.5987	NPC301760
Remote Similarity	0.5986	NPC101139
Remote Similarity	0.5984	NPC307456
Remote Similarity	0.5976	NPC469760
Remote Similarity	0.5976	NPC73952
Remote Similarity	0.5976	NPC469765
Remote Similarity	0.5976	NPC259644
Remote Similarity	0.5976	NPC469786
Remote Similarity	0.5976	NPC25008
Remote Similarity	0.5976	NPC469763
Remote Similarity	0.5974	NPC300299
Remote Similarity	0.5974	NPC173295
Remote Similarity	0.5969	NPC108800
Remote Similarity	0.5966	NPC233936
Remote Similarity	0.5964	NPC123241
Remote Similarity	0.5964	NPC61013
Remote Similarity	0.596	NPC89490
Remote Similarity	0.596	NPC280807
Remote Similarity	0.596	NPC314431
Remote Similarity	0.596	NPC9856
Remote Similarity	0.596	NPC226662
Remote Similarity	0.5954	NPC475097
Remote Similarity	0.5952	NPC282339
Remote Similarity	0.5952	NPC99632
Remote Similarity	0.5949	NPC59084
Remote Similarity	0.5949	NPC115611
Remote Similarity	0.5948	NPC471322
Remote Similarity	0.5948	NPC256893
Remote Similarity	0.5944	NPC125416
Remote Similarity	0.5944	NPC147957
Remote Similarity	0.5939	NPC471458
Remote Similarity	0.5939	NPC80597
Remote Similarity	0.5939	NPC212376
Remote Similarity	0.5939	NPC38736
Remote Similarity	0.5939	NPC75540
Remote Similarity	0.5939	NPC211572
Remote Similarity	0.5939	NPC70922
Remote Similarity	0.5938	NPC472242
Remote Similarity	0.5935	NPC198988
Remote Similarity	0.5928	NPC193410
Remote Similarity	0.5928	NPC36495
Remote Similarity	0.5928	NPC135141
Remote Similarity	0.5928	NPC92796
Remote Similarity	0.5926	NPC109787
Remote Similarity	0.5926	NPC321617
Remote Similarity	0.5923	NPC471309
Remote Similarity	0.5921	NPC329896
Remote Similarity	0.5921	NPC475105
Remote Similarity	0.5921	NPC475090
Remote Similarity	0.5918	NPC39818
Remote Similarity	0.5917	NPC40779
Remote Similarity	0.5915	NPC205652
Remote Similarity	0.5915	NPC117032
Remote Similarity	0.5912	NPC63157
Remote Similarity	0.5912	NPC473868
Remote Similarity	0.5906	NPC30445
Remote Similarity	0.5906	NPC201700
Remote Similarity	0.5906	NPC111233
Remote Similarity	0.5904	NPC285469
Remote Similarity	0.5904	NPC315257
Remote Similarity	0.5901	NPC159856
Remote Similarity	0.5901	NPC470440
Remote Similarity	0.5897	NPC218268
Remote Similarity	0.5894	NPC328590
Remote Similarity	0.5893	NPC248117
Remote Similarity	0.589	NPC124005
Remote Similarity	0.589	NPC318086
Remote Similarity	0.589	NPC187951
Remote Similarity	0.5887	NPC15839
Remote Similarity	0.5886	NPC68354
Remote Similarity	0.5886	NPC43477
Remote Similarity	0.5886	NPC104483
Remote Similarity	0.5882	NPC275467
Remote Similarity	0.5882	NPC22079
Remote Similarity	0.5875	NPC314186
Remote Similarity	0.5875	NPC136002
Remote Similarity	0.5873	NPC258046
Remote Similarity	0.5867	NPC245244
Remote Similarity	0.5867	NPC166424
Remote Similarity	0.5867	NPC146373
Remote Similarity	0.5867	NPC250476
Remote Similarity	0.5865	NPC317642
Remote Similarity	0.5862	NPC37423
Remote Similarity	0.5862	NPC189812
Remote Similarity	0.5862	NPC329688
Remote Similarity	0.5862	NPC264580
Remote Similarity	0.5862	NPC275305
Remote Similarity	0.5858	NPC293458
Remote Similarity	0.5858	NPC85651
Remote Similarity	0.5855	NPC194562
Remote Similarity	0.5855	NPC187231
Remote Similarity	0.5854	NPC206592
Remote Similarity	0.585	NPC71684
Remote Similarity	0.5849	NPC469767
Remote Similarity	0.5849	NPC469784
Remote Similarity	0.5849	NPC469779
Remote Similarity	0.5849	NPC469780
Remote Similarity	0.5849	NPC469783

Drug Structure

NPD2036 OpenBabel08211701392D 26 27 0 0 0 0 0 0 0 0999 V2000 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 0.8660 -1.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 0.0000 -0.0000 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 4.3301 -1.5000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 22 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 12 17 1 0 0 0 0 13 19 1 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 20 2 3 0 0 0 16 21 1 0 0 0 0 16 22 1 0 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP001422
DrugBank	DB04953
ChEMBL	CHEMBL41355
IUPHAR/BPS	2601
PharmaGKB	PA144997862
KEGG Drug	D09569
PubChem CID	121892
ChEBI	68584
CAS Number	150812-12-7

Drug Properties

Molecular Weight	303.14
ALogP	0.1429
MLogP	2.56
XLogP	3.787
HDA	5
HBD	3
Rotatable Bonds	10
TPSA	79.87
RO5 Violation	0