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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:45 UTC
Update Date2018-05-17 04:18:45 UTC
HMDB IDHMDB0002273
Secondary Accession Numbers
  • HMDB0001344
  • HMDB01344
  • HMDB02273
Metabolite Identification
Common Name4-Hydroxy-L-glutamic acid
Description4-Hydroxy-L-glutamic acid is an intermediate in the metabolism of gamma-hydroxyglutamic acid. Specifically 4-Hydroxy-L-glutamic acid combines with 2-oxoglutarate to produce 4-hydroxy-2-oxoglutarate and glutamate. The reaction can be described as: 4-Hydroxy-L-glutamate + 2-Oxoglutarate <=> 4-Hydroxy-2-oxoglutarate + L-Glutamate. This reaction is catalyzed by 4-hydroxyglutamate aminotransferase (PMID 13948827 ).
Structure
Thumb
Synonyms
ValueSource
beta-HydroxyglutamateMeSH
beta-Hydroxyglutamic acidMeSH
erythro-L-BHGAMeSH
Hydroxyglutamic acid, (DL)-isomerMeSH
Hydroxyglutamic acid, erythro-(DL)-isomerMeSH
Hydroxyglutamic acid, erythro-(L)-isomerMeSH
Hydroxyglutamic acid, sodium saltMeSH
threo-L-BHGAMeSH
Chemical FormulaC5H9NO5
Average Molecular Weight163.129
Monoisotopic Molecular Weight163.048072394
IUPAC Name2-amino-4-hydroxypentanedioic acid
Traditional Namehydroxyglutamic acid
CAS Registry Number2485-33-8
SMILES
NC(CC(O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H9NO5/c6-2(4(8)9)1-3(7)5(10)11/h2-3,7H,1,6H2,(H,8,9)(H,10,11)
InChI KeyHBDWQSHEVMSFGY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Alpha-amino acid
  • Amino fatty acid
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Fatty acid
  • Fatty acyl
  • 1,3-aminoalcohol
  • Secondary alcohol
  • Amino acid
  • Carboxylic acid
  • Primary amine
  • Primary aliphatic amine
  • Organopnictogen compound
  • Alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic oxide
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Process

Naturally occurring process:

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 Solubility565 g/LALOGPS
logP-3.7ALOGPS
logP-4.2ChemAxon
logS-0.34ALOGPS
pKa (Strongest Acidic)1.68ChemAxon
pKa (Strongest Basic)9.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.85 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.74 m³·mol⁻¹ChemAxon
Polarizability14.24 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Location
  • Liver
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound839
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceDucrocq, Claire; Decottignies-Le Marechal, Paulette; Azerad, Robert. Synthesis of L-glutamic acid stereospecifically labeled at C-4 with deuterium. Journal of Labelled Compounds and Radiopharmaceuticals (1985), 22(1), 61-70.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. GOLDSTONE A, ADAMS E: Metabolism of gamma-hydroxyglutamic acid. I. Conversion to alpha-hydroxy-gamma-ketoglutarate by purified glutamic-aspartic transaminase to rat liver. J Biol Chem. 1962 Nov;237:3476-85. [PubMed:13948827 ]
  2. Alaux S, Kusk M, Sagot E, Bolte J, Jensen AA, Brauner-Osborne H, Gefflaut T, Bunch L: Chemoenzymatic synthesis of a series of 4-substituted glutamate analogues and pharmacological characterization at human glutamate transporters subtypes 1-3. J Med Chem. 2005 Dec 15;48(25):7980-92. [PubMed:16335922 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Irreversible conversion of delta-1-pyrroline-5-carboxylate (P5C), derived either from proline or ornithine, to glutamate. This is a necessary step in the pathway interconnecting the urea and tricarboxylic acid cycles. The preferred substrate is glutamic gamma-semialdehyde, other substrates include succinic, glutaric and adipic semialdehydes.
Gene Name:
ALDH4A1
Uniprot ID:
P30038
Molecular weight:
55117.24
Reactions
Pyrroline hydroxycarboxylic acid + NAD + Water → 4-Hydroxy-L-glutamic acid + NADH + Hydrogen Iondetails
Pyrroline hydroxycarboxylic acid + NADP + Water → 4-Hydroxy-L-glutamic acid + NADPH + Hydrogen Iondetails
4-Hydroxy-L-glutamic acid + NADH + Hydrogen Ion → L-4-Hydroxyglutamate semialdehyde + NAD + Waterdetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
Reactions
4-Hydroxy-L-glutamic acid + Oxoglutaric acid → D-4-Hydroxy-2-oxoglutarate + L-Glutamic aciddetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
Reactions
4-Hydroxy-L-glutamic acid + Oxoglutaric acid → D-4-Hydroxy-2-oxoglutarate + L-Glutamic aciddetails
General function:
Involved in proline dehydrogenase activity
Specific function:
Converts proline to delta-1-pyrroline-5-carboxylate.
Gene Name:
PRODH
Uniprot ID:
O43272
Molecular weight:
56196.675
Reactions
4-Hydroxy-L-glutamic acid + NADH + Hydrogen Ion → L-4-Hydroxyglutamate semialdehyde + NAD + Waterdetails