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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:18 UTC
Update Date2020-06-15 17:04:52 UTC
HMDB IDHMDB0012283
Secondary Accession Numbers
  • HMDB12283
Metabolite Identification
Common NamePrephenate
DescriptionPrephenate (CAS: 126-49-8), also known as prephenic acid, 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. Prephenic acid is an example of an achiral (optically inactive) molecule which has two pseudoasymmetric atoms (i.e. stereogenic but not chirotopic centers): the C1 and the C4 cyclohexadiene ring atoms. Prephenate is an extremely weak basic (essentially neutral) compound (based on its pKa). Prephenate exists in all living species, ranging from bacteria to humans. Outside of the human body, prephenate has been detected, but not quantified in, several different foods, such as American pokeweeds, breadnut tree seeds, common wheats, swiss chards, and breadfruits. This could make prephenate a potential biomarker for the consumption of these foods. The other stereoisomer, i.e. trans or, better, (1r, 4r), is called epiprephenic. It has been shown that of the two possible diastereoisomers, the natural prephenic acid is one that has both substituents at higher priority (according to CIP rules) on the two pseudoasymmetric carbons, i.e. the carboxyl and the hydroxyl groups, in the cis configuration, or (1s, 4s) according to the new IUPAC stereochemistry rules (2013). It is biosynthesized by a [3,3]-sigmatropic Claisen rearrangement of chorismate. Prephenic acid, commonly also known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine, as well as of a large number of secondary metabolites of the shikimate pathway.
Structure
Data?1583173770
Synonyms
ValueSource
cis-1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acidChEBI
cis-Prephenic acidChEBI
Prephenic acid, cisChEBI
cis-1-Carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoateGenerator
cis-1-Carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoic acidGenerator
cis-1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoateGenerator
cis-1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoateGenerator
cis-1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoic acidGenerator
cis-PrephenateGenerator
Prephenate, cisGenerator
PREPHENateGenerator
(1S,4S)-PrephenateGenerator
Prephenic acidKEGG
1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acidHMDB
1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acidHMDB
1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propionic acidHMDB
1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoic acidHMDB
1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propionic acidHMDB
PPAHMDB
cis-1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propionic acidHMDB
cis-1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propionic acidHMDB
Chemical FormulaC10H10O6
Average Molecular Weight226.1828
Monoisotopic Molecular Weight226.047738052
IUPAC Name(1s,4s)-1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
Traditional Nameprephenic acid
CAS Registry Number87664-40-2
SMILES
O[C@H]1C=C[C@](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)/t6-,10+
InChI KeyFPWMCUPFBRFMLH-XGAOUMNUSA-N
Chemical Taxonomy
Description 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
  • 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

Route of exposure:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014u-6920000000-ef53f0db72ce3c5aa0c4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9610000000-b3ced3fa2b10936d8535Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-0950000000-783758ab15df97a404b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bu9-1910000000-9f4b0bd1d617cf85c5b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-00e996c97c569d0bb94bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1790000000-a8695b0e797b6ea4a6c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01sr-1920000000-f17d05344ee2d90f01c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-8900000000-b4238cbdb48e66836fb1Spectrum
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 IDDB08427
Phenol Explorer Compound IDNot Available
FooDB IDFDB028914
KNApSAcK IDC00019632
Chemspider ID16735981
KEGG Compound IDC00254
BioCyc IDPREPHENATE
BiGG IDNot Available
Wikipedia LinkPrephenic_acid
METLIN IDNot Available
PubChem Compound363602639
PDB IDNot Available
ChEBI ID84387
Food Biomarker OntologyNot Available
VMH IDNot Available
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 ]