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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:46:54 UTC
Update Date2019-07-23 06:35:12 UTC
HMDB IDHMDB0041900
Secondary Accession Numbers
  • HMDB41900
Metabolite Identification
Common Namegamma-Carboxyglutamic acid
DescriptionCarboxyglutamic acid (or the conjugate base, carboxyglutamate), is an uncommon amino acid introduced into proteins by a post-translational carboxylation of glutamic acid residues. This modification is found, for example, in clotting factors and other proteins of the coagulation cascade. This modification introduces an affinity for calcium ions. In the blood coagulation cascade, Vitamin K is required to introduce gamma-carboxylation of clotting factors II, VII, IX, X and protein Z.
Structure
Data?1563863712
Synonyms
ValueSource
g-CarboxyglutamateGenerator
g-Carboxyglutamic acidGenerator
gamma-CarboxyglutamateGenerator
Γ-carboxyglutamateGenerator
Γ-carboxyglutamic acidGenerator
1-Carboxyglutamic acidHMDB
3-Amino-1,1,3-propanetricarboxylic acidHMDB
1 Carboxyglutamic acidHMDB
gamma CarboxyglutamateHMDB
gamma Carboxyglutamic acidHMDB
1-Aminopropane-1,3,3-tricarboxylateGenerator
gamma-Carboxyglutamic acidMeSH
Chemical FormulaC6H9NO6
Average Molecular Weight191.1388
Monoisotopic Molecular Weight191.042987025
IUPAC Name1-aminopropane-1,3,3-tricarboxylic acid
Traditional Namecarboxyglutamic acid
CAS Registry Number53445-96-8
SMILES
NC(CC(C(O)=O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H9NO6/c7-3(6(12)13)1-2(4(8)9)5(10)11/h2-3H,1,7H2,(H,8,9)(H,10,11)(H,12,13)
InChI KeyUHBYWPGGCSDKFX-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
  • Tricarboxylic acid or derivatives
  • Amino fatty acid
  • 1,3-dicarbonyl compound
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility22.5 g/LALOGPS
logP-3ALOGPS
logP-3.6ChemAxon
logS-0.93ALOGPS
pKa (Strongest Acidic)1.48ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area137.92 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.58 m³·mol⁻¹ChemAxon
Polarizability16.25 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, Positivesplash10-0f6y-8900000000-75ef53a4dcd9d280245aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-5292000000-637a364ee3e0fdba68a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0095-0900000000-ebd5517a54362ca1151dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fba-1900000000-d38618a5dd7fa30bd4fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-5900000000-906c8a6982d2dfadd401Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002e-0900000000-bf4a6a37e51ef3a03f6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fba-1900000000-a8bd6fdb47ffff956587Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0umi-6900000000-36a6d4c84e065e15ccfdSpectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID37241
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarboxyglutamic acid
METLIN IDNot Available
PubChem Compound40772
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available