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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 21:06:30 UTC
Update Date2022-09-22 18:35:15 UTC
HMDB IDHMDB0341425
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Methylglutamic acid
Description4-Methylglutamic acid, also known as 4-methylglutamate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 4-Methylglutamic acid is a very strong basic compound (based on its pKa). N-Methyl-l-glutamic acid (methylglutamate) is a chemical derivative of glutamic acid in which a methyl group has been added to the amino group. It can also be demethylated by methylglutamate dehydrogenase to regenerate glutamic acid. Biosynthetically, it is produced from methylamine and glutamic acid by the enzyme methylamine—glutamate N-methyltransferase. It is an intermediate in methane metabolism.
Structure
Thumb
Synonyms
ValueSource
4-MethylglutamateGenerator
4-Methylglutamic acid, (DL)-isomerMeSH
4-Methylglutamic acid, (L)-isomerMeSH
Threo-gamma-methylglutamateMeSH
4-Methylglutamic acid, 2-(13)C-labeled, (DL)-isomerMeSH
4-Methylglutamic acid, threo-(L)-isomerMeSH
4-Methylglutamic acid, sodium salt, (erythro)-isomerMeSH
2S,4R-4-MethylglutamateMeSH
2-Amino-4-methylpentanedioateGenerator
Chemical FormulaC6H11NO4
Average Molecular Weight161.157
Monoisotopic Molecular Weight161.068807838
IUPAC Name2-amino-4-methylpentanedioic acid
Traditional Name2-amino-4-methylpentanedioic acid
CAS Registry NumberNot Available
SMILES
CC(CC(N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H11NO4/c1-3(5(8)9)2-4(7)6(10)11/h3-4H,2,7H2,1H3,(H,8,9)(H,10,11)
InChI KeyKRKRAOXTGDJWNI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Amino fatty acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-3.3ALOGPS
logP-2.7ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)2.01ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.86 m³·mol⁻¹ChemAxon
Polarizability15.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Methyl-L-glutamic acid
METLIN IDNot Available
PubChem Compound5365
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Meister I, Zhang P, Sinha A, Skold CM, Wheelock AM, Izumi T, Chaleckis R, Wheelock CE: High-Precision Automated Workflow for Urinary Untargeted Metabolomic Epidemiology. Anal Chem. 2021 Mar 30;93(12):5248-5258. doi: 10.1021/acs.analchem.1c00203. Epub 2021 Mar 19. [PubMed:33739820 ]