Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-17 08:37:49 UTC

Update Date

2023-02-21 17:17:06 UTC

HMDB ID

HMDB0005015

Secondary Accession Numbers

HMDB05015

Metabolite Identification

Common Name

Gabapentin

Description

Gabapentin was originally developed as a chemical analogue of gamma-aminobutyric acid (GABA) to reduce the spinal reflex for the treatment of spasticity and was found to have anticonvulsant activity in various seizure models. In addition, it also displays antinociceptive activity in various animal pain models. Clinically, gabapentin is indicated as an add-on medication for the treatment of partial seizures, and neuropathic pain. It was also claimed to be beneficial in several other clinical disorders such as anxiety, bipolar disorder, and hot flashes. The possible mechanisms or targets involved in the multiple therapeutic actions of gabapentin have been actively studied. Since gabapentin was developed, several hypotheses had been proposed for its action mechanisms. They include selectively activating the heterodimeric GABA(B) receptors consisting of GABA(B1a) and GABA(B2) subunits, selectively enhancing the NMDA current at GABAergic interneurons, or blocking AMPA-receptor-mediated transmission in the spinal cord, binding to the L-alpha-amino acid transporter, activating ATP-sensitive K(+) channels, activating hyperpolarization-activated cation channels, and modulating Ca(2+) current by selectively binding to the specific binding site of [(3)H]gabapentin, the alpha(2)delta subunit of voltage-dependent Ca(2+) channels. Different mechanisms might be involved in different therapeutic actions of gabapentin. In this review, we summarized the recent progress in the findings proposed for the antinociceptive action mechanisms of gabapentin and suggest that the alpha(2)delta subunit of spinal N-type Ca(2+) channels is very likely the analgesic action target of gabapentin. (PMID: 16474201 ).

Structure

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

HMDB0005015
     RDKit          3D
Gabapentin
 29 29  0  0  0  0  0  0  0  0999 V2000
    1.6023   -2.1244   -0.1060 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502   -1.1746   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -0.0246    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    0.8404    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3659    0.2593    1.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2886   -0.8997    1.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875    0.9822    2.0007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5642    0.9072   -0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9842    0.3961   -0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6001    0.7414    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501    0.3815    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965   -0.6080    1.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027   -2.9122    0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636   -2.5658   -0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2743   -0.8256   -1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2081   -1.7133   -1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9484    1.7437    1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784    1.3350   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1170    1.3427    1.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1074    1.0085   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6027    1.9117   -0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0508   -0.6896   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099    0.9821   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5665    0.2096    0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7302    1.8529    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399    1.2360    2.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2671   -0.2004    2.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204   -0.9526    2.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1654   -1.4394    0.6902 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  1  0
  5  6  2  0
  5  7  1  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  3  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  4 17  1  0
  4 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
M  END

HMDB0005015
     RDKit          3D
Gabapentin
 29 29  0  0  0  0  0  0  0  0999 V2000
    1.6023   -2.1244   -0.1060 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502   -1.1746   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -0.0246    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    0.8404    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3659    0.2593    1.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2886   -0.8997    1.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875    0.9822    2.0007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5642    0.9072   -0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9842    0.3961   -0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6001    0.7414    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501    0.3815    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965   -0.6080    1.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027   -2.9122    0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636   -2.5658   -0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2743   -0.8256   -1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2081   -1.7133   -1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9484    1.7437    1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784    1.3350   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1170    1.3427    1.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1074    1.0085   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6027    1.9117   -0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0508   -0.6896   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099    0.9821   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5665    0.2096    0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7302    1.8529    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399    1.2360    2.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2671   -0.2004    2.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204   -0.9526    2.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1654   -1.4394    0.6902 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  1  0
  5  6  2  0
  5  7  1  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  3  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  4 17  1  0
  4 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 996                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       8.948   2.874   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.948   0.206   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       3.557   1.540   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.867   0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.534  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.201  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.534  -2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.201  -2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.867  -2.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.637   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.097   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.177   1.540   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   11                                                            
CONECT    4    5    6   10   11                                             
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6    9                                                       
CONECT    9    7    8                                                       
CONECT   10    4   12                                                       
CONECT   11    3    4                                                       
CONECT   12    1    2   10                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0005015
HETATM    1  N1  UNL     1       1.602  -2.124  -0.106  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.750  -1.175  -0.748  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.308  -0.025   0.105  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.376   0.840   0.648  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.366   0.259   1.548  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.289  -0.900   1.971  1.00  0.00           O  
HETATM    7  O2  UNL     1       3.488   0.982   2.001  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.564   0.907  -0.779  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.984   0.396  -0.835  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.600   0.741   0.524  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.650   0.381   1.645  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.596  -0.608   1.170  1.00  0.00           C  
HETATM   13  H1  UNL     1       1.103  -2.912   0.360  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.264  -2.566  -0.787  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.274  -0.826  -1.671  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.208  -1.713  -1.043  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.948   1.744   1.190  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.978   1.335  -0.186  1.00  0.00           H  
HETATM   19  H7  UNL     1       4.117   1.343   1.322  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.107   1.008  -1.773  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.603   1.912  -0.289  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.051  -0.690  -0.984  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.510   0.982  -1.597  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.566   0.210   0.587  1.00  0.00           H  
HETATM   25  H13 UNL     1      -2.730   1.853   0.564  1.00  0.00           H  
HETATM   26  H14 UNL     1      -1.240   1.236   2.180  1.00  0.00           H  
HETATM   27  H15 UNL     1      -2.267  -0.200   2.391  1.00  0.00           H  
HETATM   28  H16 UNL     1      -0.020  -0.953   2.023  1.00  0.00           H  
HETATM   29  H17 UNL     1      -1.165  -1.439   0.690  1.00  0.00           H  
CONECT    1    2   13   14
CONECT    2    3   15   16
CONECT    3    4    8   12
CONECT    4    5   17   18
CONECT    5    6    6    7
CONECT    7   19
CONECT    8    9   20   21
CONECT    9   10   22   23
CONECT   10   11   24   25
CONECT   11   12   26   27
CONECT   12   28   29
END

HMDB0005015
     RDKit          3D
Gabapentin
 29 29  0  0  0  0  0  0  0  0999 V2000
    1.6023   -2.1244   -0.1060 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502   -1.1746   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -0.0246    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    0.8404    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3659    0.2593    1.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2886   -0.8997    1.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875    0.9822    2.0007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5642    0.9072   -0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9842    0.3961   -0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6001    0.7414    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501    0.3815    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965   -0.6080    1.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027   -2.9122    0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636   -2.5658   -0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2743   -0.8256   -1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2081   -1.7133   -1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9484    1.7437    1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784    1.3350   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1170    1.3427    1.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1074    1.0085   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6027    1.9117   -0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0508   -0.6896   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099    0.9821   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5665    0.2096    0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7302    1.8529    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399    1.2360    2.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2671   -0.2004    2.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204   -0.9526    2.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1654   -1.4394    0.6902 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  1  0
  5  6  2  0
  5  7  1  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  3  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  4 17  1  0
  4 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(Aminomethyl)cyclohexaneacetic acid	ChEBI
Gabapentina	ChEBI
Gabapentine	ChEBI
Gabapentinum	ChEBI
Neurontin	ChEBI
Gralise	Kegg
1-(Aminomethyl)cyclohexaneacetate	Generator
Aclonium	HMDB
Gabapentino	HMDB
Gabapetin	HMDB
Novo-gabapentine	HMDB
Convalis	HMDB
Gabapentin hexal	HMDB
PMS-Gabapentin	HMDB
Gabapentin stada	HMDB
Gabapentin-ratiopharm	HMDB
Novo-gabapentin	HMDB
Apo-gabapentin	HMDB
Gabapentin ratiopharm	HMDB
NovoGabapentin	HMDB
Apo gabapentin	HMDB
ApoGabapentin	HMDB
Novo gabapentin	HMDB

Chemical Formula

C₉H₁₇NO₂

Average Molecular Weight

171.2368

Monoisotopic Molecular Weight

171.125928793

IUPAC Name

2-[1-(aminomethyl)cyclohexyl]acetic acid

Traditional Name

gabapentin

CAS Registry Number

60142-96-3

SMILES

NCC1(CC(O)=O)CCCCC1

InChI Identifier

InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)

InChI Key

UGJMXCAKCUNAIE-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
Amino fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

gamma-amino acid (CHEBI:42797 )

Ontology

Physiological effect

Health effect

Observation

Sedation (HMDB: HMDB0005015)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17517538)

Organ

Brain (HMDB: HMDB0005015)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Cellular substructure

Cytoplasm (HMDB: HMDB0005015)
Extracellular (HMDB: HMDB0005015)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005015)

Source

Exogenous

Exogenous (HMDB: HMDB0005015)

Environmental

Wastewater (HMDB: HMDB0005015)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0005015)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anticonvulsant (HMDB: HMDB0005015)
Anticonvulsant (HMDB: HMDB0005015)

Biological role

Calcium antagonist (HMDB: HMDB0005015)

Environmental role

Environmental contaminant (HMDB: HMDB0005015)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 - 167 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.10	SANGSTER (1994)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	138.613	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001294

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.34 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-1.3	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	4.63	ChemAxon
pKa (Strongest Basic)	9.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.33 m³·mol⁻¹	ChemAxon
Polarizability	18.92 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	138.405	31661259
DarkChem	[M-H]-	134.385	31661259
DeepCCS	[M+H]+	145.708	30932474
DeepCCS	[M-H]-	143.01	30932474
DeepCCS	[M-2H]-	179.068	30932474
DeepCCS	[M+Na]+	154.489	30932474
AllCCS	[M+H]+	138.4	32859911
AllCCS	[M+H-H2O]+	134.3	32859911
AllCCS	[M+NH4]+	142.2	32859911
AllCCS	[M+Na]+	143.3	32859911
AllCCS	[M-H]-	138.7	32859911
AllCCS	[M+Na-2H]-	139.9	32859911
AllCCS	[M+HCOO]-	141.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gabapentin	NCC1(CC(O)=O)CCCCC1	2405.8	Standard polar	33892256
Gabapentin	NCC1(CC(O)=O)CCCCC1	1507.8	Standard non polar	33892256
Gabapentin	NCC1(CC(O)=O)CCCCC1	1510.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gabapentin,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1(CN)CCCCC1	1547.6	Semi standard non polar	33892256
Gabapentin,1TMS,isomer #2	C[Si](C)(C)NCC1(CC(=O)O)CCCCC1	1692.6	Semi standard non polar	33892256
Gabapentin,2TMS,isomer #1	C[Si](C)(C)NCC1(CC(=O)O[Si](C)(C)C)CCCCC1	1675.8	Semi standard non polar	33892256
Gabapentin,2TMS,isomer #1	C[Si](C)(C)NCC1(CC(=O)O[Si](C)(C)C)CCCCC1	1732.3	Standard non polar	33892256
Gabapentin,2TMS,isomer #1	C[Si](C)(C)NCC1(CC(=O)O[Si](C)(C)C)CCCCC1	1974.8	Standard polar	33892256
Gabapentin,2TMS,isomer #2	C[Si](C)(C)N(CC1(CC(=O)O)CCCCC1)[Si](C)(C)C	1879.2	Semi standard non polar	33892256
Gabapentin,2TMS,isomer #2	C[Si](C)(C)N(CC1(CC(=O)O)CCCCC1)[Si](C)(C)C	1779.7	Standard non polar	33892256
Gabapentin,2TMS,isomer #2	C[Si](C)(C)N(CC1(CC(=O)O)CCCCC1)[Si](C)(C)C	2113.8	Standard polar	33892256
Gabapentin,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1(CN([Si](C)(C)C)[Si](C)(C)C)CCCCC1	1872.4	Semi standard non polar	33892256
Gabapentin,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1(CN([Si](C)(C)C)[Si](C)(C)C)CCCCC1	1889.8	Standard non polar	33892256
Gabapentin,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1(CN([Si](C)(C)C)[Si](C)(C)C)CCCCC1	1938.5	Standard polar	33892256
Gabapentin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1(CN)CCCCC1	1778.4	Semi standard non polar	33892256
Gabapentin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC1(CC(=O)O)CCCCC1	1940.0	Semi standard non polar	33892256
Gabapentin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1(CC(=O)O[Si](C)(C)C(C)(C)C)CCCCC1	2140.2	Semi standard non polar	33892256
Gabapentin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1(CC(=O)O[Si](C)(C)C(C)(C)C)CCCCC1	2131.8	Standard non polar	33892256
Gabapentin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1(CC(=O)O[Si](C)(C)C(C)(C)C)CCCCC1	2230.7	Standard polar	33892256
Gabapentin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC1(CC(=O)O)CCCCC1)[Si](C)(C)C(C)(C)C	2309.0	Semi standard non polar	33892256
Gabapentin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC1(CC(=O)O)CCCCC1)[Si](C)(C)C(C)(C)C	2167.5	Standard non polar	33892256
Gabapentin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC1(CC(=O)O)CCCCC1)[Si](C)(C)C(C)(C)C	2310.8	Standard polar	33892256
Gabapentin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC1	2538.2	Semi standard non polar	33892256
Gabapentin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC1	2467.1	Standard non polar	33892256
Gabapentin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC1	2273.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gabapentin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9300000000-1b1c66a2b9ea4333921d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gabapentin GC-MS (1 TMS) - 70eV, Positive	splash10-00ai-9520000000-9cbc5f48f228d49f903c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gabapentin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-QTOF , negative-QTOF	splash10-00di-0900000000-bccc9bd5f1637db7b6c7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-QTOF , negative-QTOF	splash10-00di-0900000000-67139ca9559173bf9859	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-QTOF , negative-QTOF	splash10-0006-9000000000-bfe6527f738e4c67eb2b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-QTOF , positive-QTOF	splash10-00di-0900000000-bb175ef297a289e1936b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-QTOF , positive-QTOF	splash10-0udr-0900000000-258d4493623d0ab7b415	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-QTOF , positive-QTOF	splash10-0f79-0900000000-bc24764f394c6fee34fd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-ITFT , positive-QTOF	splash10-0udi-0900000000-006ecd4a58af763b087f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-ITFT , positive-QTOF	splash10-00di-0900000000-012c52738f11970adb8d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-ITFT , positive-QTOF	splash10-00di-0900000000-8f0d390195aa406adb5d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-ITFT , positive-QTOF	splash10-0uk9-0900000000-72f8d5cb88eda76dab56	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-ITFT , positive-QTOF	splash10-0udi-3900000000-b634b4e7144ec6ffdc83	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-ITFT , positive-QTOF	splash10-0ktn-9800000000-20c4131179b228ab3440	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-ITFT , positive-QTOF	splash10-00ke-9300000000-dd9d44ed4f16961ed075	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-ITFT , positive-QTOF	splash10-00di-0900000000-f9a7deaa778e9d893ee8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-ITFT , positive-QTOF	splash10-00di-0900000000-4f85e6ac9fd91a3e3b81	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-ITFT , positive-QTOF	splash10-0uk9-0900000000-d3a4c5658e343cf3cf8d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-ITFT , positive-QTOF	splash10-0udi-3900000000-712133d5b9eae1b27ffb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-ITFT , positive-QTOF	splash10-0ktn-9800000000-c652847259e0851b428e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gabapentin LC-ESI-ITFT , positive-QTOF	splash10-00ke-9200000000-77e258cf26b045a7e46e	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin 10V, Positive-QTOF	splash10-0kmi-0900000000-bd606c1e84a1821141d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin 20V, Positive-QTOF	splash10-0a6r-1900000000-7e1f93e356d99c221d79	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin 40V, Positive-QTOF	splash10-0a4l-9400000000-e7cad8847543c27e9be7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin 10V, Negative-QTOF	splash10-00fr-0900000000-46b0ef53eef895d16407	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin 20V, Negative-QTOF	splash10-00fr-1900000000-49d03843c6afc2b38719	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gabapentin 40V, Negative-QTOF	splash10-0a4i-7900000000-21b2e487e51f606cc2ad	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Brain

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.31 +/- 0.012 uM	Adult (>18 years old)	Both	Normal	17517538	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB00996

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023587

KNApSAcK ID

Not Available

Chemspider ID

3328

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gabapentin

METLIN ID

2989

PubChem Compound

3446

PDB ID

Not Available

ChEBI ID

42797

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Satzinger, Gerhard; Hartenstein, Johannes; Herrmann, Manfred; Heldt, Wolfgang. Cyclic amino acids. Ger. Offen. (1976), 16 pp. CODEN: GWXXBX DE 2460891 19760701 CAN 85:94679 AN 1976:494679

Material Safety Data Sheet (MSDS)

Not Available

General References

Nemeroff CB: The role of GABA in the pathophysiology and treatment of anxiety disorders. Psychopharmacol Bull. 2003;37(4):133-46. [PubMed:15131523 ]
Di Trapani G, Mei D, Marra C, Mazza S, Capuano A: Gabapentin in the prophylaxis of migraine: a double-blind randomized placebo-controlled study. Clin Ter. 2000 May-Jun;151(3):145-8. [PubMed:10958046 ]
Bisaga A, Aharonovich E, Garawi F, Levin FR, Rubin E, Raby WN, Nunes EV: A randomized placebo-controlled trial of gabapentin for cocaine dependence. Drug Alcohol Depend. 2006 Feb 28;81(3):267-74. Epub 2005 Oct 5. [PubMed:16169160 ]
Petroff OA, Rothman DL, Behar KL, Lamoureux D, Mattson RH: The effect of gabapentin on brain gamma-aminobutyric acid in patients with epilepsy. Ann Neurol. 1996 Jan;39(1):95-9. [PubMed:8572673 ]
Taylor CP, Gee NS, Su TZ, Kocsis JD, Welty DF, Brown JP, Dooley DJ, Boden P, Singh L: A summary of mechanistic hypotheses of gabapentin pharmacology. Epilepsy Res. 1998 Feb;29(3):233-49. [PubMed:9551785 ]
Czapinski P, Blaszczyk B, Czuczwar SJ: Mechanisms of action of antiepileptic drugs. Curr Top Med Chem. 2005;5(1):3-14. [PubMed:15638774 ]
Cheng JK, Chiou LC: Mechanisms of the antinociceptive action of gabapentin. J Pharmacol Sci. 2006;100(5):471-86. Epub 2006 Feb 11. [PubMed:16474201 ]

Enzymes

Enzyme Details

1. Branched-chain-amino-acid aminotransferase, cytosolic

General function:: Involved in catalytic activity
Specific function:: Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
Gene Name:: BCAT1
Uniprot ID:: P54687
Molecular weight:: 38644.77

Enzyme Details

2. Adenosine receptor A1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: ADORA1
Uniprot ID:: P30542
Molecular weight:: 36511.3

Enzyme Details

3. Voltage-dependent calcium channel subunit alpha-2/delta-1

General function:: Involved in metal ion binding
Specific function:: The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Plays an important role in excitation-contraction coupling
Gene Name:: CACNA2D1
Uniprot ID:: P54289
Molecular weight:: 124566.9

Enzyme Details

4. Voltage-dependent calcium channel subunit alpha-2/delta-2

General function:: Involved in calcium channel activity
Specific function:: The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Acts as a regulatory subunit for P/Q-type calcium channel (CACNA1A), N-type (CACNA1B), L-type (CACNA1C OR CACNA1D) and possibly T-type (CACNA1G). Overexpression induces apoptosis
Gene Name:: CACNA2D2
Uniprot ID:: Q9NY47
Molecular weight:: 129875.2

Enzyme Details

5. Voltage-dependent N-type calcium channel subunit alpha-1B

General function:: Involved in ion channel activity
Specific function:: Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1B gives rise to N-type calcium currents. N-type calcium channels belong to the 'high-voltage activated' (HVA) group and are blocked by omega-conotoxin-GVIA (omega-CTx-GVIA) and by omega-agatoxin- IIIA (omega-Aga-IIIA). They are however insensitive to dihydropyridines (DHP), and omega-agatoxin-IVA (omega-Aga-IVA). Calcium channels containing alpha-1B subunit may play a role in directed migration of immature neurons
Gene Name:: CACNA1B
Uniprot ID:: Q00975
Molecular weight:: 262493.8

Showing metabocard for Gabapentin (HMDB0005015)

MOL for HMDB0005015 (Gabapentin)

3D MOL for HMDB0005015 (Gabapentin)

3D SDF for HMDB0005015 (Gabapentin)

3D-SDF for HMDB0005015 (Gabapentin)

PDB for HMDB0005015 (Gabapentin)

3D PDB for HMDB0005015 (Gabapentin)

SMILES for HMDB0005015 (Gabapentin)

INCHI for HMDB0005015 (Gabapentin)

Structure for HMDB0005015 (Gabapentin)

3D Structure for HMDB0005015 (Gabapentin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes