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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:18 UTC
Update Date2017-10-23 19:06:02 UTC
HMDB IDHMDB0012283
Secondary Accession Numbers
  • HMDB12283
Metabolite Identification
Common NamePrephenate
DescriptionPrephenic acid, more commonly known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine.
Structure
Thumb
Synonyms
ValueSource
1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acidChEBI
1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acidChEBI
1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvateGenerator
Prephenic acidGenerator
1-Carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoateGenerator
1-Carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoic acidGenerator
1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoateGenerator
1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoateGenerator
1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoic acidGenerator
PREHMDB
Chemical FormulaC10H10O6
Average Molecular Weight226.1828
Monoisotopic Molecular Weight226.047738052
IUPAC Name1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
Traditional Nameprephenic acid
CAS Registry Number126-49-8
SMILES
OC1C=CC(CC(=O)C(O)=O)(C=C1)C(O)=O
InChI Identifier
InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)
InChI KeyFPWMCUPFBRFMLH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassKeto acids and derivatives
Direct ParentGamma-keto acids and derivatives
Alternative Parents
Substituents
  • Gamma-keto acid
  • Dicarboxylic acid or derivatives
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

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 Solubility36 g/LALOGPS
logP-0.31ALOGPS
logP0.061ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.55 m³·mol⁻¹ChemAxon
Polarizability19.73 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-004u-5930000000-ab2b31a4c4dfd40ceddbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-004u-9810000000-ac9f3a0c71b3c5665bf8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014u-8910000000-3415a97033f86fa8c8a8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004u-5930000000-ab2b31a4c4dfd40ceddbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004u-9810000000-ac9f3a0c71b3c5665bf8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9610000000-b3ced3fa2b10936d8535View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004l-8009100000-38ca188548d74699664bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0960000000-977e79544dc4467ac727View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bu9-1910000000-ad1d0e019512e236b48eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-328dfece2609b4273be8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1790000000-740f63025e2d1901bfccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06v0-1920000000-23a6bf28fe9915f6fca3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-8900000000-a949dc8f9457a7974670View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028914
KNApSAcK IDNot Available
Chemspider ID1001
KEGG Compound IDC00254
BioCyc IDPREPHENATE
BiGG IDNot Available
Wikipedia LinkPrephenic_acid
METLIN IDNot Available
PubChem Compound1028
PDB IDNot Available
ChEBI ID16666
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. METZENBERG RL, MITCHELL HK: Isolation of prephenic acid from Neurospora. Arch Biochem Biophys. 1956 Sep;64(1):51-6. [PubMed:13363412 ]
  2. GAMBORG OL, SIMPSON FJ: PREPARATION OF PREPHENIC ACID AND ITS CONVERSION TO PHENYLALANINE AND TYROSINE BY PLANT ENZYMES. Can J Biochem. 1964 May;42:583-91. [PubMed:14185725 ]