NPASS drugs

Drug Information

Drug ID:	NPD2257
Drug Name:	Gabapentin Enacarbil
Molecular Formula:	C16H27NO6
Canonical SMILES:	CC(OC(=O)C(C)C)OC(=NCC1(CCCCC1)CC(=O)O)O
Standard InCHI:	InChI=1S/C16H27NO6/c1-11(2)14(20)22-12(3)23-15(21)17-10-16(9-13(18)19)7-5-4-6-8-16/h11-12H,4-10H2,1-3H3,(H,17,21)(H,18,19)
Standard InCHIKey:	TZDUHAJSIBHXDL-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD2257

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	50
0.1-0.2	962
0.2-0.3	12095
0.3-0.4	8310
0.4-0.5	7965
0.5-0.6	1472
0.6-0.7	35
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	0.7361	NPC302188
Remote Similarity	0.6786	NPC473984
Remote Similarity	0.6667	NPC473899
Remote Similarity	0.6471	NPC316242
Remote Similarity	0.6395	NPC478017
Remote Similarity	0.6395	NPC315131
Remote Similarity	0.6395	NPC315535
Remote Similarity	0.6386	NPC43219
Remote Similarity	0.631	NPC86064
Remote Similarity	0.6292	NPC47135
Remote Similarity	0.6267	NPC319279
Remote Similarity	0.6265	NPC469940
Remote Similarity	0.625	NPC470283
Remote Similarity	0.6211	NPC270005
Remote Similarity	0.6211	NPC208537
Remote Similarity	0.6154	NPC227051
Remote Similarity	0.6143	NPC477878
Remote Similarity	0.6143	NPC324793
Remote Similarity	0.6125	NPC476330
Remote Similarity	0.6104	NPC470363
Remote Similarity	0.6092	NPC70996
Remote Similarity	0.6087	NPC83839
Remote Similarity	0.6087	NPC314679
Remote Similarity	0.6071	NPC478227
Remote Similarity	0.6064	NPC33398
Remote Similarity	0.6047	NPC179858
Remote Similarity	0.6047	NPC477934
Remote Similarity	0.6044	NPC145748
Remote Similarity	0.6044	NPC155670
Remote Similarity	0.6044	NPC95478
Remote Similarity	0.6024	NPC478256
Remote Similarity	0.6	NPC477729
Remote Similarity	0.6	NPC271572
Remote Similarity	0.6	NPC21844
Remote Similarity	0.6	NPC474870
Remote Similarity	0.6	NPC249754
Remote Similarity	0.598	NPC227622
Remote Similarity	0.5978	NPC79308
Remote Similarity	0.5977	NPC477933
Remote Similarity	0.5977	NPC477932
Remote Similarity	0.5977	NPC330017
Remote Similarity	0.5976	NPC41542
Remote Similarity	0.5972	NPC305182
Remote Similarity	0.5955	NPC474702
Remote Similarity	0.5952	NPC477929
Remote Similarity	0.5949	NPC306750
Remote Similarity	0.5946	NPC72722
Remote Similarity	0.5942	NPC55023
Remote Similarity	0.5926	NPC325117
Remote Similarity	0.5926	NPC469791
Remote Similarity	0.5926	NPC322319
Remote Similarity	0.5926	NPC326651
Remote Similarity	0.5909	NPC477918
Remote Similarity	0.5897	NPC475821
Remote Similarity	0.5895	NPC322966
Remote Similarity	0.5895	NPC470009
Remote Similarity	0.5895	NPC470284
Remote Similarity	0.5882	NPC185419
Remote Similarity	0.5882	NPC477641
Remote Similarity	0.5882	NPC320865
Remote Similarity	0.5882	NPC184550
Remote Similarity	0.5882	NPC477643
Remote Similarity	0.5876	NPC165904
Remote Similarity	0.5876	NPC475878
Remote Similarity	0.5876	NPC179517
Remote Similarity	0.5875	NPC474552
Remote Similarity	0.5875	NPC235788
Remote Similarity	0.587	NPC320936
Remote Similarity	0.5857	NPC308301
Remote Similarity	0.5854	NPC268736
Remote Similarity	0.5854	NPC477931
Remote Similarity	0.5854	NPC470109
Remote Similarity	0.5843	NPC243594
Remote Similarity	0.5843	NPC314858
Remote Similarity	0.5843	NPC51695
Remote Similarity	0.5843	NPC31031
Remote Similarity	0.5843	NPC253703
Remote Similarity	0.5843	NPC200085
Remote Similarity	0.5842	NPC474952
Remote Similarity	0.5833	NPC469941
Remote Similarity	0.5833	NPC64466
Remote Similarity	0.5833	NPC476734
Remote Similarity	0.5833	NPC319671
Remote Similarity	0.5833	NPC252032
Remote Similarity	0.5816	NPC277721
Remote Similarity	0.5816	NPC267266
Remote Similarity	0.5816	NPC469998
Remote Similarity	0.5814	NPC291228
Remote Similarity	0.5814	NPC308096
Remote Similarity	0.5806	NPC277918
Remote Similarity	0.5806	NPC25802
Remote Similarity	0.5806	NPC101138
Remote Similarity	0.5806	NPC82492
Remote Similarity	0.5806	NPC51135
Remote Similarity	0.5806	NPC476523
Remote Similarity	0.5806	NPC71626
Remote Similarity	0.5802	NPC314103
Remote Similarity	0.5795	NPC476601
Remote Similarity	0.5789	NPC252714
Remote Similarity	0.5789	NPC475773
Remote Similarity	0.5783	NPC206601
Remote Similarity	0.5783	NPC470110
Remote Similarity	0.5783	NPC286842
Remote Similarity	0.5778	NPC327674
Remote Similarity	0.5778	NPC474754
Remote Similarity	0.5778	NPC216090
Remote Similarity	0.5773	NPC477782
Remote Similarity	0.5765	NPC477850
Remote Similarity	0.5765	NPC91369
Remote Similarity	0.5758	NPC474554
Remote Similarity	0.5755	NPC137453
Remote Similarity	0.5753	NPC50457
Remote Similarity	0.5747	NPC477930
Remote Similarity	0.5745	NPC478111
Remote Similarity	0.5732	NPC215987
Remote Similarity	0.5732	NPC19311
Remote Similarity	0.5732	NPC470108
Remote Similarity	0.5732	NPC230047
Remote Similarity	0.5732	NPC306805
Remote Similarity	0.573	NPC307865
Remote Similarity	0.573	NPC474404
Remote Similarity	0.573	NPC469867
Remote Similarity	0.573	NPC169389
Remote Similarity	0.5729	NPC292345
Remote Similarity	0.5729	NPC203170
Remote Similarity	0.5728	NPC42320
Remote Similarity	0.5728	NPC188453
Remote Similarity	0.5727	NPC28224
Remote Similarity	0.5714	NPC82315
Remote Similarity	0.5714	NPC36616
Remote Similarity	0.5714	NPC119329
Remote Similarity	0.5714	NPC470956
Remote Similarity	0.5714	NPC477783
Remote Similarity	0.5714	NPC261616
Remote Similarity	0.5714	NPC472853
Remote Similarity	0.5714	NPC290445
Remote Similarity	0.5701	NPC475150
Remote Similarity	0.57	NPC215570
Remote Similarity	0.5699	NPC474266
Remote Similarity	0.5699	NPC323180
Remote Similarity	0.5698	NPC474403
Remote Similarity	0.5698	NPC72343
Remote Similarity	0.5696	NPC472020
Remote Similarity	0.5696	NPC472019
Remote Similarity	0.5696	NPC226602
Remote Similarity	0.5696	NPC469924
Remote Similarity	0.5688	NPC246399
Remote Similarity	0.5688	NPC470534
Remote Similarity	0.5688	NPC34977
Remote Similarity	0.5684	NPC244174
Remote Similarity	0.5684	NPC474062
Remote Similarity	0.5684	NPC470657
Remote Similarity	0.5682	NPC472311
Remote Similarity	0.5679	NPC325773
Remote Similarity	0.5676	NPC470540
Remote Similarity	0.5676	NPC314084
Remote Similarity	0.5667	NPC199965
Remote Similarity	0.5667	NPC476732
Remote Similarity	0.5663	NPC42060
Remote Similarity	0.5657	NPC470656
Remote Similarity	0.5652	NPC229584
Remote Similarity	0.5652	NPC327002
Remote Similarity	0.5652	NPC14203
Remote Similarity	0.5648	NPC473578
Remote Similarity	0.5647	NPC241265
Remote Similarity	0.5647	NPC295788
Remote Similarity	0.5647	NPC477642
Remote Similarity	0.5647	NPC178541
Remote Similarity	0.5647	NPC285003
Remote Similarity	0.5644	NPC240673
Remote Similarity	0.5644	NPC475785
Remote Similarity	0.5644	NPC17578
Remote Similarity	0.5644	NPC475765
Remote Similarity	0.5638	NPC125253
Remote Similarity	0.5638	NPC253975
Remote Similarity	0.5638	NPC192025
Remote Similarity	0.5638	NPC175419
Remote Similarity	0.5634	NPC30195
Remote Similarity	0.5634	NPC12438
Remote Similarity	0.5632	NPC475230
Remote Similarity	0.5632	NPC109510
Remote Similarity	0.5625	NPC31349
Remote Similarity	0.5625	NPC288952
Remote Similarity	0.5625	NPC478126
Remote Similarity	0.5625	NPC265580
Remote Similarity	0.5625	NPC472021
Remote Similarity	0.562	NPC475472
Remote Similarity	0.5618	NPC4209
Remote Similarity	0.5618	NPC474020
Remote Similarity	0.5604	NPC477346
Remote Similarity	0.5604	NPC201276
Remote Similarity	0.5604	NPC294748
Remote Similarity	0.5604	NPC146992
Remote Similarity	0.5604	NPC158302
Remote Similarity	0.5604	NPC22742
Remote Similarity	0.5604	NPC477344
Remote Similarity	0.5604	NPC85759
Remote Similarity	0.5604	NPC80891

Drug Structure

NPD2257 OpenBabel08211701392D 25 25 0 0 1 0 0 0 0 0999 V2000 1.0860 -5.9850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1387 -7.2098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3449 -5.0191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 0.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1201 -6.2438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6378 -4.3120 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.6628 1.6002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5870 -5.5367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1895 -2.6390 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 0.4483 -1.6730 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2611 1.9829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4562 2.2090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5529 -5.7956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 -2.8978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3282 -4.5708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8966 -3.3461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3257 3.2004 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4836 -2.1907 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 1 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 16 1 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 12 22 1 0 0 0 0 12 23 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 15 17 2 3 0 0 0 15 21 1 0 0 0 0 15 23 1 0 0 0 0 19 24 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank
ChEMBL
IUPHAR/BPS	7560
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	329.18
ALogP	0.0591
MLogP	2.45
XLogP	3.43
HDA	7
HBD	2
Rotatable Bonds	14
TPSA	105.42
RO5 Violation	0