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Showing metabocard for 2-Keto-glutaramic acid (HMDB0001552)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-09-17 18:58:10 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
Data?1600369090
MOLSDFPDBSMILESInChI
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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility26.7 g/LALOGPS
logP-1.4ALOGPS
logP-0.92ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)2.97ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.71 m³·mol⁻¹ChemAxon
Polarizability12.56 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, Positivesplash10-0f6x-9300000000-364f00f83f2890864bf3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-9600000000-f15721df49885ecdf65eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-2eb098e06d8301b0bce6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06w9-6900000000-d802d6bf63187e0b9714Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-0aaaa6f3f4d3183b6b21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2900000000-c4ab5bdf984680f19900Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f96-9800000000-6a2a8c2f9da457c041c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-76ca31bd526f5a4086c8Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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
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 ID
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

Enzyme Details
1. Kynurenine--oxoglutarate transaminase 1
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
L-Glutamine + Phenylpyruvic acid → 2-Keto-glutaramic acid + L-Phenylalaninedetails
Enzyme Details
2. Omega-amidase NIT2
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