Record Information
Version3.6
Creation Date2009-02-23 13:32:29 UTC
Update Date2013-05-29 19:46:51 UTC
HMDB IDHMDB11714
Secondary Accession NumbersNone
Metabolite Identification
Common NameVanilpyruvic acid
DescriptionVanilpyruvic acid is a catecholamine metabolite and precursor to vanilactic acid. Accumulation in urine is indicative of Aromatic L-aminoacid decarboxylase deficiency (PMID 16288991 ).
Structure
Thumb
Synonyms
  1. Vanil pyruvic acid
Chemical FormulaC10H10O5
Average Molecular Weight210.1834
Monoisotopic Molecular Weight210.05282343
IUPAC Name3-(4-hydroxy-3-methoxyphenyl)-2-oxopropanoic acid
Traditional IUPAC Name3-(4-hydroxy-3-methoxyphenyl)-2-oxopropanoic acid
CAS Registry Number1081-71-6
SMILES
COC1=C(O)C=CC(CC(=O)C(O)=O)=C1
InChI Identifier
InChI=1S/C10H10O5/c1-15-9-5-6(2-3-7(9)11)4-8(12)10(13)14/h2-3,5,11H,4H2,1H3,(H,13,14)
InChI KeyYGQHQTMRZPHIBB-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassBenzyl Alcohols and Derivatives
Sub ClassPhenylpyruvic Acid Derivatives
Other Descriptors
  • Organic Compounds
  • a small molecule(Cyc)
Substituents
  • Alkyl Aryl Ether
  • Alpha Keto Acid
  • Anisole
  • Carboxylic Acid
  • Ketone
  • Methoxyphenol
  • Phenol
  • Phenol Derivative
Direct ParentPhenylpyruvic Acid Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 solubility1.3 g/LALOGPS
logP1.36ALOGPS
logP1.44ChemAxon
logS-2.2ALOGPS
pKa (strongest acidic)2.73ChemAxon
pKa (strongest basic)-4.9ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count2ChemAxon
polar surface area83.83ChemAxon
rotatable bond count4ChemAxon
refractivity51.16ChemAxon
polarizability19.53ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
UrineDetected and Quantified10 +/- 2 umol/mmol creatinineInfant (0-1 year old)MaleAromatic L-amino acid decarboxylase deficiency
Associated Disorders and Diseases
Disease References
Aromatic L-amino acid decarboxylase deficiency
  • Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. Pubmed: 16288991
Associated OMIM IDs
    107930 (Aromatic L-amino acid decarboxylase deficiency)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028400
KNApSAcK IDNot Available
Chemspider ID13501
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11714
Metagene LinkHMDB11714
METLIN IDNot Available
PubChem Compound14124
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. Pubmed: 16288991