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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2008-10-29 15:20:57 UTC
Update Date2020-02-26 21:34:36 UTC
HMDB IDHMDB0011172
Secondary Accession Numbers
  • HMDB0029162
  • HMDB11172
  • HMDB29162
Metabolite Identification
Common Namegamma-Glutamylvaline
Descriptiongamma-Glutamylvaline is a dipeptide composed of gamma-glutamate and valine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. gamma-Glutamylvaline belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. It is found in urine (PMID: 3782411 ).
Structure
Data?1582752876
Synonyms
ValueSource
γ-Glu-ValHMDB, Generator
γ-L-Glu-L-ValHMDB
γ-GlutamylvalineHMDB, Generator
γ-L-Glutamyl-L-valineHMDB
L-γ-Glutamyl-L-valineHMDB
N-γ-GlutamylvalineHMDB
N-L-γ-GlutamylvalineHMDB
N-L-γ-Glutamyl-L-valineHMDB
gamma-Glu-ValHMDB
gamma-L-Glu-L-ValHMDB
gamma-GlutamylvalineHMDB, ChEBI
gamma-L-Glutamyl-L-valineHMDB
L-gamma-Glutamyl-L-valineHMDB
N-L-gamma-GlutamylvalineHMDB
N-L-gamma-Glutamyl-L-valineHMDB
L-gamma-Glu-L-ValChEBI
g-GlutamylvalineGenerator
L-g-Glu-L-ValGenerator
L-γ-Glu-L-ValGenerator
g-Glu-ValGenerator, HMDB
N-γ-L-Glutamyl-L-valineHMDB
N-gamma-GlutamylvalineHMDB
N-gamma-L-Glutamyl-L-valineHMDB
Chemical FormulaC10H18N2O5
Average Molecular Weight246.263
Monoisotopic Molecular Weight246.121571688
IUPAC Name(2S)-2-amino-4-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}butanoic acid
Traditional Name(2S)-2-amino-4-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}butanoic acid
CAS Registry Number2746-34-1
SMILES
CC(C)[C@H](NC(=O)CC[C@H](N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C10H18N2O5/c1-5(2)8(10(16)17)12-7(13)4-3-6(11)9(14)15/h5-6,8H,3-4,11H2,1-2H3,(H,12,13)(H,14,15)(H,16,17)/t6-,8-/m0/s1
InChI KeyAQAKHZVPOOGUCK-XPUUQOCRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Valine or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Methyl-branched fatty acid
  • Branched fatty acid
  • N-acyl-amine
  • Fatty acyl
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.02 g/LALOGPS
logP-2.9ALOGPS
logP-2.9ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.09ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity57.58 m³·mol⁻¹ChemAxon
Polarizability24.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ugj-0490000000-570014eb4534edfce899Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-107i-5940000000-8fdd03caafd389b6e73bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9400000000-8ab7d89b0c6e2e1eff17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0190000000-01f7213e4f145c229f03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fvj-3980000000-fd64f03e4003670f690fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-9400000000-30468bbfca4ce7249b34Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5378716
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7015683
PDB IDNot Available
ChEBI ID68848
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. [PubMed:3782411 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]