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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:29:30 UTC

Update Date

2021-09-26 23:05:14 UTC

HMDB ID

HMDB0252567

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Gabapentin enacarbil

Description

Gabapentin enacarbil, also known as horizant or XP 13512, belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. Gabapentin enacarbil is a drug which is used for the treatment of adult restless legs syndrome (rls) and postherpetic neuralgia (phn). Based on a literature review a significant number of articles have been published on Gabapentin enacarbil. This compound has been identified in human blood as reported by (PMID: 31557052 ). Gabapentin enacarbil is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Gabapentin enacarbil is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0252567
     RDKit          3D
Gabapentin enacarbil
 50 50  0  0  0  0  0  0  0  0999 V2000
    3.1987    2.6986    0.6540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    1.3413    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133    0.9657    0.5067 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370    0.7815   -0.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7368    0.9571   -1.5669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220    0.4076    0.1935 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8239    0.2228   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0685   -0.1700   -0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9266   -1.4544    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6087   -2.6253   -0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5362   -2.5373   -1.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3794   -3.8665    0.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1640   -0.2824   -1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7843    1.0546   -1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4116    1.7036   -0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879    0.9116    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4733    0.8860    1.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8279    0.3606    0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6052   -0.3737   -0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025   -0.1828   -1.6738 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5830   -1.4026    0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5880   -0.6720    0.8961 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2534   -2.0878   -1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2719    3.2719    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6072    2.4478    1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532    3.2605    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8672    1.4480   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420    0.2747    1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0634    1.1856   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532   -0.5221   -1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8442   -1.6212    1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0900   -1.2857    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8765   -3.8790    1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7197   -0.6553   -2.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9294   -1.0315   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0122    1.7238   -1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5947    0.8459   -2.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0223    2.7473   -0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5000    1.7615   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3633   -0.1200    1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3449    1.4548    1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0615    1.8795    0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0760    0.6059    2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -2.1989    0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6067   -1.0609    0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6190    0.4195    0.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2668   -0.7451    1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5998   -2.9426   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2277   -2.4633   -0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3309   -1.4374   -2.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  2 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 17  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
M  END


  Mrv1652306071717262D          

 23 23  0  0  0  0            999 V2000
   -1.9136   -2.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1991   -1.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1991   -1.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136   -0.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -1.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -1.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4968   -0.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3302   -0.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333   -0.2467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500    0.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8468    0.1231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1635    1.1335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2593    0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0843    0.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8468    1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4968    1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3219    1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0843    2.2665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7343    2.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7343    0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3219   -0.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7344    0.6812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7344   -0.7476    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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252567

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C(=O)OC(C)OC(=O)NCC1(CC(O)=O)CCCCC1

> <INCHI_IDENTIFIER>
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)

> <INCHI_KEY>
TZDUHAJSIBHXDL-UHFFFAOYSA-N

> <FORMULA>
C16H27NO6

> <MOLECULAR_WEIGHT>
329.393

> <EXACT_MASS>
329.183837593

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
34.37975228649671

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1-{[({1-[(2-methylpropanoyl)oxy]ethoxy}carbonyl)amino]methyl}cyclohexyl)acetic acid

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
2.7634692416666664

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.000695674166991

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.352854024691864

> <JCHEM_PKA_STRONGEST_BASIC>
-7.146365794149963

> <JCHEM_POLAR_SURFACE_AREA>
101.93

> <JCHEM_REFRACTIVITY>
81.69269999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gabapentin enacarbil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252567
     RDKit          3D
Gabapentin enacarbil
 50 50  0  0  0  0  0  0  0  0999 V2000
    3.1987    2.6986    0.6540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    1.3413    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133    0.9657    0.5067 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370    0.7815   -0.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7368    0.9571   -1.5669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220    0.4076    0.1935 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8239    0.2228   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0685   -0.1700   -0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9266   -1.4544    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6087   -2.6253   -0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5362   -2.5373   -1.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3794   -3.8665    0.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1640   -0.2824   -1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7843    1.0546   -1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4116    1.7036   -0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879    0.9116    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4733    0.8860    1.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8279    0.3606    0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6052   -0.3737   -0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025   -0.1828   -1.6738 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5830   -1.4026    0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5880   -0.6720    0.8961 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2534   -2.0878   -1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2719    3.2719    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6072    2.4478    1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532    3.2605    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8672    1.4480   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420    0.2747    1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0634    1.1856   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532   -0.5221   -1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8442   -1.6212    1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0900   -1.2857    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8765   -3.8790    1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7197   -0.6553   -2.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9294   -1.0315   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0122    1.7238   -1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5947    0.8459   -2.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0223    2.7473   -0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5000    1.7615   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3633   -0.1200    1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3449    1.4548    1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0615    1.8795    0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0760    0.6059    2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -2.1989    0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6067   -1.0609    0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6190    0.4195    0.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2668   -0.7451    1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5998   -2.9426   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2277   -2.4633   -0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3309   -1.4374   -2.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  2 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 17  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
M  END

HEADER    PROTEIN                                 07-JUN-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUN-17         0                                  
HETATM    1  C   UNK     0      -3.572  -4.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.238  -3.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.238  -1.921   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.572  -1.151   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.906  -1.921   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.906  -3.461   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.661  -0.062   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.483  -0.062   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.995  -0.461   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.093   0.628   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.581   0.230   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.305   2.116   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.351   1.563   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.891   1.563   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.581   2.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.661   2.897   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.201   2.897   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.891   4.231   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.971   4.231   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.971   1.563   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.201  -0.062   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.971   1.272   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.971  -1.396   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7    8                                             
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4   21                                                       
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16   19   20                                                  
CONECT   18   16                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21    7   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0252567
HETATM    1  C1  UNL     1       3.199   2.699   0.654  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.896   1.341   0.005  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.613   0.966   0.507  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.537   0.781  -0.349  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.737   0.957  -1.567  1.00  0.00           O  
HETATM    6  N1  UNL     1      -0.722   0.408   0.193  1.00  0.00           N  
HETATM    7  C4  UNL     1      -1.824   0.223  -0.725  1.00  0.00           C  
HETATM    8  C5  UNL     1      -3.069  -0.170  -0.008  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.927  -1.454   0.755  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.609  -2.625  -0.068  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.536  -2.537  -1.309  1.00  0.00           O  
HETATM   12  O4  UNL     1      -2.379  -3.866   0.514  1.00  0.00           O  
HETATM   13  C8  UNL     1      -4.164  -0.282  -1.056  1.00  0.00           C  
HETATM   14  C9  UNL     1      -4.784   1.055  -1.388  1.00  0.00           C  
HETATM   15  C10 UNL     1      -5.412   1.704  -0.174  1.00  0.00           C  
HETATM   16  C11 UNL     1      -4.988   0.912   1.059  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.473   0.886   1.032  1.00  0.00           C  
HETATM   18  O5  UNL     1       3.828   0.361   0.416  1.00  0.00           O  
HETATM   19  C13 UNL     1       4.605  -0.374  -0.435  1.00  0.00           C  
HETATM   20  O6  UNL     1       4.502  -0.183  -1.674  1.00  0.00           O  
HETATM   21  C14 UNL     1       5.583  -1.403   0.015  1.00  0.00           C  
HETATM   22  C15 UNL     1       6.588  -0.672   0.896  1.00  0.00           C  
HETATM   23  C16 UNL     1       6.253  -2.088  -1.135  1.00  0.00           C  
HETATM   24  H1  UNL     1       2.272   3.272   0.836  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.607   2.448   1.672  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.953   3.261   0.091  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.867   1.448  -1.110  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.842   0.275   1.216  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.063   1.186  -1.260  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.553  -0.522  -1.482  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.844  -1.621   1.381  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.090  -1.286   1.497  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.877  -3.879   1.402  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.720  -0.655  -2.021  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.929  -1.031  -0.778  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.012   1.724  -1.793  1.00  0.00           H  
HETATM   37  H14 UNL     1      -5.595   0.846  -2.118  1.00  0.00           H  
HETATM   38  H15 UNL     1      -5.022   2.747  -0.013  1.00  0.00           H  
HETATM   39  H16 UNL     1      -6.500   1.761  -0.244  1.00  0.00           H  
HETATM   40  H17 UNL     1      -5.363  -0.120   1.001  1.00  0.00           H  
HETATM   41  H18 UNL     1      -5.345   1.455   1.959  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.062   1.879   0.765  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.076   0.606   2.030  1.00  0.00           H  
HETATM   44  H21 UNL     1       5.087  -2.199   0.632  1.00  0.00           H  
HETATM   45  H22 UNL     1       7.607  -1.061   0.779  1.00  0.00           H  
HETATM   46  H23 UNL     1       6.619   0.419   0.652  1.00  0.00           H  
HETATM   47  H24 UNL     1       6.267  -0.745   1.956  1.00  0.00           H  
HETATM   48  H25 UNL     1       5.600  -2.943  -1.444  1.00  0.00           H  
HETATM   49  H26 UNL     1       7.228  -2.463  -0.787  1.00  0.00           H  
HETATM   50  H27 UNL     1       6.331  -1.437  -2.036  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   18   27
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   28
CONECT    7    8   29   30
CONECT    8    9   13   17
CONECT    9   10   31   32
CONECT   10   11   11   12
CONECT   12   33
CONECT   13   14   34   35
CONECT   14   15   36   37
CONECT   15   16   38   39
CONECT   16   17   40   41
CONECT   17   42   43
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   23   44
CONECT   22   45   46   47
CONECT   23   48   49   50
END

HMDB0252567
     RDKit          3D
Gabapentin enacarbil
 50 50  0  0  0  0  0  0  0  0999 V2000
    3.1987    2.6986    0.6540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    1.3413    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133    0.9657    0.5067 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5370    0.7815   -0.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7368    0.9571   -1.5669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220    0.4076    0.1935 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8239    0.2228   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0685   -0.1700   -0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9266   -1.4544    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6087   -2.6253   -0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5362   -2.5373   -1.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3794   -3.8665    0.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1640   -0.2824   -1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7843    1.0546   -1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4116    1.7036   -0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879    0.9116    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4733    0.8860    1.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8279    0.3606    0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6052   -0.3737   -0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025   -0.1828   -1.6738 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5830   -1.4026    0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5880   -0.6720    0.8961 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2534   -2.0878   -1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2719    3.2719    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6072    2.4478    1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532    3.2605    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8672    1.4480   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420    0.2747    1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0634    1.1856   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532   -0.5221   -1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8442   -1.6212    1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0900   -1.2857    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8765   -3.8790    1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7197   -0.6553   -2.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9294   -1.0315   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0122    1.7238   -1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5947    0.8459   -2.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0223    2.7473   -0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5000    1.7615   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3633   -0.1200    1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3449    1.4548    1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0615    1.8795    0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0760    0.6059    2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -2.1989    0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6067   -1.0609    0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6190    0.4195    0.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2668   -0.7451    1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5998   -2.9426   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2277   -2.4633   -0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3309   -1.4374   -2.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  2 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 17  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Gabapentina enacarbilo	ChEBI
Gabapentine enacarbil	ChEBI
Gabapentinum enacarbilum	ChEBI
Horizant	ChEBI
XP 13512	ChEBI
XP-13512	ChEBI
XP13512	ChEBI
1-(((alpha-Isobutanoyloxyethoxy)carbonyl)aminomethyl)-1-cyclohexaneacetic acid	MeSH

Chemical Formula

C₁₆H₂₇NO₆

Average Molecular Weight

329.393

Monoisotopic Molecular Weight

329.183837593

IUPAC Name

2-(1-{[({1-[(2-methylpropanoyl)oxy]ethoxy}carbonyl)amino]methyl}cyclohexyl)acetic acid

Traditional Name

gabapentin enacarbil

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)OC(C)OC(=O)NCC1(CC(O)=O)CCCCC1

InChI Identifier

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)

InChI Key

TZDUHAJSIBHXDL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Dicarboxylic acid or derivatives
Carbamic acid ester
Carboxylic acid ester
Carbonic acid derivative
Acetal
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

carbamate ester (CHEBI:68840 )
monocarboxylic acid (CHEBI:68840 )
carboxylic ester (CHEBI:68840 )
acetal (CHEBI:68840 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.45	ALOGPS
logP	2.76	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	101.93 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	81.69 m³·mol⁻¹	ChemAxon
Polarizability	34.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	181.096	30932474
DeepCCS	[M-H]-	178.738	30932474
DeepCCS	[M-2H]-	211.984	30932474
DeepCCS	[M+Na]+	187.211	30932474
AllCCS	[M+H]+	177.1	32859911
AllCCS	[M+H-H2O]+	174.5	32859911
AllCCS	[M+NH4]+	179.6	32859911
AllCCS	[M+Na]+	180.3	32859911
AllCCS	[M-H]-	178.2	32859911
AllCCS	[M+Na-2H]-	178.9	32859911
AllCCS	[M+HCOO]-	179.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gabapentin enacarbil	CC(C)C(=O)OC(C)OC(=O)NCC1(CC(O)=O)CCCCC1	3136.2	Standard polar	33892256
Gabapentin enacarbil	CC(C)C(=O)OC(C)OC(=O)NCC1(CC(O)=O)CCCCC1	2047.7	Standard non polar	33892256
Gabapentin enacarbil	CC(C)C(=O)OC(C)OC(=O)NCC1(CC(O)=O)CCCCC1	2312.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gabapentin enacarbil,2TMS,isomer #1	CC(OC(=O)C(C)C)OC(=O)N(CC1(CC(=O)O[Si](C)(C)C)CCCCC1)[Si](C)(C)C	2330.5	Semi standard non polar	33892256
Gabapentin enacarbil,2TMS,isomer #1	CC(OC(=O)C(C)C)OC(=O)N(CC1(CC(=O)O[Si](C)(C)C)CCCCC1)[Si](C)(C)C	2315.6	Standard non polar	33892256
Gabapentin enacarbil,2TMS,isomer #1	CC(OC(=O)C(C)C)OC(=O)N(CC1(CC(=O)O[Si](C)(C)C)CCCCC1)[Si](C)(C)C	2827.6	Standard polar	33892256
Gabapentin enacarbil,2TBDMS,isomer #1	CC(OC(=O)C(C)C)OC(=O)N(CC1(CC(=O)O[Si](C)(C)C(C)(C)C)CCCCC1)[Si](C)(C)C(C)(C)C	2813.2	Semi standard non polar	33892256
Gabapentin enacarbil,2TBDMS,isomer #1	CC(OC(=O)C(C)C)OC(=O)N(CC1(CC(=O)O[Si](C)(C)C(C)(C)C)CCCCC1)[Si](C)(C)C(C)(C)C	2701.7	Standard non polar	33892256
Gabapentin enacarbil,2TBDMS,isomer #1	CC(OC(=O)C(C)C)OC(=O)N(CC1(CC(=O)O[Si](C)(C)C(C)(C)C)CCCCC1)[Si](C)(C)C(C)(C)C	3049.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gabapentin enacarbil GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9620000000-9b26c179b9f76d59c1b3	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gabapentin enacarbil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gabapentin enacarbil GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gabapentin enacarbil GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gabapentin enacarbil GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gabapentin enacarbil GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin enacarbil 10V, Positive-QTOF	splash10-00xr-3930000000-5ff0bf78db7a21021ad6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin enacarbil 20V, Positive-QTOF	splash10-00di-5910000000-6edc04f089ebe39118ee	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin enacarbil 40V, Positive-QTOF	splash10-05fr-4900000000-22476df81442eb5caa2c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin enacarbil 10V, Negative-QTOF	splash10-0002-2910000000-ed48dae697f2bf95eabf	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin enacarbil 20V, Negative-QTOF	splash10-0007-7900000000-5eefbe0a7d00980bd21e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin enacarbil 40V, Negative-QTOF	splash10-0006-9700000000-e496fc1ed93bd25fd9b5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin enacarbil 10V, Positive-QTOF	splash10-029y-3954000000-f8346aaef4b005c544c8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin enacarbil 20V, Positive-QTOF	splash10-0fef-6910000000-1a7801ca93b86f431167	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin enacarbil 40V, Positive-QTOF	splash10-052f-9400000000-2a83707c167522f67d7e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin enacarbil 10V, Negative-QTOF	splash10-000f-9110000000-07f972f266339845b4c3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin enacarbil 20V, Negative-QTOF	splash10-006x-9800000000-43d4e810ba3856d8ca0f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin enacarbil 40V, Negative-QTOF	splash10-00di-9700000000-920eef9b4a34dd23f5ac	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08872

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8059607

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gabapentin_enacarbil

METLIN ID

Not Available

PubChem Compound

9883933

PDB ID

Not Available

ChEBI ID

68840

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Gabapentin enacarbil (HMDB0252567)

MOL for HMDB0252567 (Gabapentin enacarbil)

3D MOL for HMDB0252567 (Gabapentin enacarbil)

3D SDF for HMDB0252567 (Gabapentin enacarbil)

3D-SDF for HMDB0252567 (Gabapentin enacarbil)

PDB for HMDB0252567 (Gabapentin enacarbil)

3D PDB for HMDB0252567 (Gabapentin enacarbil)

SMILES for HMDB0252567 (Gabapentin enacarbil)

INCHI for HMDB0252567 (Gabapentin enacarbil)

Structure for HMDB0252567 (Gabapentin enacarbil)

3D Structure for HMDB0252567 (Gabapentin enacarbil)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra