Record Information
Version1.0
Creation Date2016-05-26 05:43:41 UTC
Update Date2016-11-09 01:21:18 UTC
Accession NumberCHEM035394
Identification
Common Name4-Hydroxy-L-glutamic acid
ClassSmall Molecule
Description4-Hydroxy-L-glutamic acid, also known as 4-hydroxy-L-glutamate or erythro-L-bhga, 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. 4-Hydroxy-L-glutamic acid is possibly soluble (in water) and a very strong basic compound (based on its pKa). 4-Hydroxy-L-glutamic acid exists in all living organisms, ranging from bacteria to humans. 4-Hydroxy-L-glutamic acid participates in a number of enzymatic reactions, within cattle. In particular, 4-Hydroxy-L-glutamic acid can be biosynthesized from pyrroline hydroxycarboxylic acid through the action of the enzyme Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial. In addition, 4-Hydroxy-L-glutamic acid can be converted into L-4-hydroxyglutamate semialdehyde through the action of the enzyme proline dehydrogenase 1, mitochondrial. In cattle, 4-hydroxy-L-glutamic acid is involved in the metabolic pathway called the arginine and proline metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
4-Hydroxy-L-glutamateGenerator
beta-HydroxyglutamateHMDB
beta-Hydroxyglutamic acidHMDB
Erythro-L-bhgaHMDB
Hydroxyglutamic acid, (DL)-isomerHMDB
Hydroxyglutamic acid, erythro-(DL)-isomerHMDB
Hydroxyglutamic acid, erythro-(L)-isomerHMDB
Hydroxyglutamic acid, sodium saltHMDB
Threo-L-bhgaHMDB
Chemical FormulaC5H7NO5
Average Molecular Mass161.113 g/mol
Monoisotopic Mass161.032 g/mol
CAS Registry Number2485-33-8
IUPAC Name2-amino-4-hydroxypentanedioic acid
Traditional Namehydroxyglutamic acid
SMILESN[C@@H](CC(O)C([O-])=O)C([O-])=O
InChI IdentifierInChI=1S/C5H9NO5/c6-2(4(8)9)1-3(7)5(10)11/h2-3,7H,1,6H2,(H,8,9)(H,10,11)/p-2/t2-,3?/m0/s1
InChI KeyHBDWQSHEVMSFGY-SCQFTWEKSA-L
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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility74.3 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0900000000-ce005fc2e4492c63491aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4i-7900000000-c99dab7460465a300d8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9100000000-9ca5dd20ed7c29d06525Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-626615b98a6b2fb5e19dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9800000000-a6e6074af92fb098b762Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9100000000-68bf4be7fd2ead3fcb1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gi0-3900000000-72a434ff0c346ae54bf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-9600000000-16a8930ac7a8ed9a8656Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9100000000-4825e58f647c6709f63eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-f33be61e6a7e963f5725Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9200000000-d4c3022fe2d2d99ba90bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-ce7c939afbade242bd22Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002273
FooDB IDFDB022938
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID1447439
BioCyc IDL-ERYTHRO-4-HYDROXY-GLUTAMATE
METLIN ID6586
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID816
ChEBI ID16338
PubChem Compound ID5460078
Kegg Compound IDC03079
YMDB IDNot Available
ECMDB IDECMDB02273
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Ducrocq, 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.
2. 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.
3. 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.