You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:45 UTC
Update Date2020-02-26 21:24:00 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
Data?1582752240
Synonyms
ValueSource
(2S,4R)-2-Amino-4-hydroxypentanedioic acidChEBI
L-Erythro-4-hydroxyglutamic acidChEBI
(2S,4R)-2-Amino-4-hydroxypentanedioateGenerator
L-Erythro-4-hydroxyglutamateGenerator
Erythro-4-hydroxy-L-glutamateGenerator
(4R)-4-Hydroxy-L-glutamateHMDB
(4R)-4-Hydroxy-L-glutamic acidHMDB
2-Hydroxy-4-aminoglutarateHMDB
2-Hydroxy-4-aminoglutaric acidHMDB
4-Hydroxy-L-glutamateHMDB
4-Hydroxy-L-glutamic acidHMDB
4-HydroxyglutamateHMDB
4-Hydroxyglutamic acidHMDB
erythro-4-Hydroxy-L-glutamic acidHMDB
(2S)-2-Amino-4-hydroxypentanedioic acidHMDB
gamma-Hydroxyglutamic acidHMDB
γ-Hydroxyglutamic acidHMDB
Chemical FormulaC5H9NO5
Average Molecular Weight163.1287
Monoisotopic Molecular Weight163.048072403
IUPAC Name(2S,4R)-2-amino-4-hydroxypentanedioic acid
Traditional Name(2S,4R)-2-amino-4-hydroxypentanedioic acid
CAS Registry Number2485-33-8
SMILES
N[C@@H](C[C@@H](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)/t2-,3+/m0/s1
InChI KeyHBDWQSHEVMSFGY-STHAYSLISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Amino fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • 1,3-aminoalcohol
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
Polarizability14.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9300000000-192385d58efcfe6d927aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fr2-1900000000-1952d82430e8d4d017ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4i-8900000000-9b552b5028c7cac0636cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9200000000-69e6a42e7b8c893be2b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3900000000-a1ac74b59a8487175409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9600000000-b341efd7d7ac7e6a7652Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9100000000-a0987d89d6b50b5ee46aSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue Locations
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>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 IDFDB022938
KNApSAcK IDNot Available
Chemspider ID389696
KEGG Compound IDC03079
BioCyc IDL-ERYTHRO-4-HYDROXY-GLUTAMATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440854
PDB IDNot Available
ChEBI ID21285
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 ]
  3. 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 ]

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