Record Information
Version1.0
Creation date2011-09-21 01:47:13 UTC
Update date2019-11-26 03:21:29 UTC
Primary IDFDB028914
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePrephenate
DescriptionPrephenate, 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. Prephenate is an extremely weak basic (essentially neutral) compound (based on its pKa). Prephenate exists in all living species, ranging from bacteria to humans. Prephenate has been detected, but not quantified in, several different foods, such as alfalfa, european plums, common mushrooms, ginkgo nuts, and lovages. This could make prephenate a potential biomarker for the consumption of these foods.
CAS Number126-49-8
Structure
Thumb
Synonyms
SynonymSource
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
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
Prephenic acidGenerator
PREHMDB
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H10O6
IUPAC name1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
InChI IdentifierInChI=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
Isomeric SMILESOC1C=CC(CC(=O)C(O)=O)(C=C1)C(O)=O
Average Molecular Weight226.1828
Monoisotopic Molecular Weight226.047738052
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-004u-5930000000-ab2b31a4c4dfd40ceddbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-004u-9810000000-ac9f3a0c71b3c5665bf8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014u-8910000000-3415a97033f86fa8c8a8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004u-5930000000-ab2b31a4c4dfd40ceddbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004u-9810000000-ac9f3a0c71b3c5665bf8JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9610000000-b3ced3fa2b10936d8535JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004l-8009100000-38ca188548d74699664bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0960000000-977e79544dc4467ac727JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bu9-1910000000-ad1d0e019512e236b48eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-328dfece2609b4273be8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1790000000-740f63025e2d1901bfccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06v0-1920000000-23a6bf28fe9915f6fca3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-8900000000-a949dc8f9457a7974670JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID1001
ChEMBL IDNot Available
KEGG Compound IDC00254
Pubchem Compound ID1028
Pubchem Substance IDNot Available
ChEBI ID29934
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12283
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference