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Record Information
Version3.6
Creation Date2009-04-06 16:22:18 UTC
Update Date2016-02-11 01:24:11 UTC
HMDB IDHMDB12283
Secondary Accession NumbersNone
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 KeyInChIKey=FPWMCUPFBRFMLH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-keto acids and derivatives
Alternative Parents
Substituents
  • Gamma-keto acid
  • Dicarboxylic acid or derivatives
  • Alpha-keto acid
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not 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 Solubility36.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.55 m3·mol-1ChemAxon
Polarizability19.73 Å3ChemAxon
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
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
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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 LinkNot Available
NuGOwiki LinkHMDB12283
Metagene LinkHMDB12283
METLIN IDNot Available
PubChem Compound1028
PDB IDNot Available
ChEBI ID16666
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available