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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:47 UTC
HMDB IDHMDB0001552
Secondary Accession Numbers
  • HMDB01552
Metabolite Identification
Common Name2-Keto-glutaramic acid
Description2-Keto-glutaramic acid, also known as 2-ketoglutaramate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Keto-glutaramic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Keto-glutaramic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, 2-Keto-glutaramic acid has been detected, but not quantified in, milk (cow). This could make 2-keto-glutaramic acid a potential biomarker for the consumption of these foods. deaminated metabolite of glutamine in csf of patients with hepatic coma; intermediate in the detoxification of ammonia in brain; structure.
Structure
Thumb
Synonyms
ValueSource
2-KetoglutaramateChEBI
alpha-KetoglutaramateChEBI
2-Ketoglutaramic acidGenerator
2-keto-GlutaramateGenerator, HMDB
a-KetoglutaramateGenerator
a-Ketoglutaramic acidGenerator
alpha-Ketoglutaramic acidGenerator
α-KetoglutaramateGenerator
α-Ketoglutaramic acidGenerator
2-OxoglutaramateHMDB, Generator
2-Oxoglutaramic acidKEGG
4-Oxoglutaramic acidHMDB
5-Amino-2,5-dioxopentanoic acidHMDB
Chemical FormulaC5H7NO4
Average Molecular Weight145.1134
Monoisotopic Molecular Weight145.037507717
IUPAC Name4-carbamoyl-2-oxobutanoic acid
Traditional Name2-keto-glutaramate
CAS Registry Number18465-19-5
SMILES
NC(=O)CCC(=O)C(O)=O
InChI Identifier
InChI=1S/C5H7NO4/c6-4(8)2-1-3(7)5(9)10/h1-2H2,(H2,6,8)(H,9,10)
InChI KeyCOJBGNAUUSNXHX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Alpha-keto acid
  • Fatty acyl
  • Fatty amide
  • Alpha-hydroxy ketone
  • Carboxamide group
  • Primary carboxylic acid amide
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022686
KNApSAcK IDNot Available
Chemspider ID47
KEGG Compound IDC00940
BioCyc ID2-KETO-GLUTARAMATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6318
PubChem Compound48
PDB IDNot Available
ChEBI ID30882
Food Biomarker OntologyNot Available
VMH IDHC00591
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLalonde, James J. Synthesis of 2-oxoglutaramate from L-glutamine. U.S. Pat. Appl. Publ. (2003), 7 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
Gene Name:
CCBL1
Uniprot ID:
Q16773
Molecular weight:
47874.765
Reactions
Glutamine + Phenylpyruvic acid → 2-Keto-glutaramic acid + Phenylalaninedetails
General function:
Not Available
Specific function:
Has a omega-amidase activity. The role of omega-amidase is to remove potentially toxic intermediates by converting alpha-ketoglutaramate and alpha-ketosuccinamate to biologically useful alpha-ketoglutarate and oxaloacetate, respectively. Overexpression decreases the colony-forming capacity of cultured cells by arresting cells in the G2 phase of the cell cycle.
Gene Name:
NIT2
Uniprot ID:
Q9NQR4
Molecular weight:
30607.645
Reactions
2-Keto-glutaramic acid + Water → Oxoglutaric acid + Ammoniadetails