Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110121
Identification
Name: prephenate
Description:A prephenate(2−) obtained by deprotonation of both carboxy groups of (1s,4s)-prephenic acid; major species at pH 7.3.
Structure
Thumb
Synonyms:
  • 1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acid
  • 1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acid
  • 1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvate
  • Prephenic acid
  • 1-Carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoate
  • 1-Carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoic acid
  • 1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoate
  • 1-Carboxy-4-hydroxy-?-oxo-2,5-cyclohexadiene-1-propanoate
  • 1-Carboxy-4-hydroxy-?-oxo-2,5-cyclohexadiene-1-propanoic acid
  • PRE
Chemical Formula: C10H8O6
Average Molecular Weight: 224.17
Monoisotopic Molecular Weight: 226.0477380536
InChI Key: FPWMCUPFBRFMLH-XGAOUMNUSA-L
InChI: 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)/p-2/t6-,10+
CAS number: 126-49-8
IUPAC Name:(1s,4s)-1-(2-carboxylato-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylate
Traditional IUPAC Name: prephenic acid
SMILES:C(=O)([O-])C(=O)CC1(C(=O)[O-])(C=CC(O)C=C1)
Chemical Taxonomy
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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassKeto acids and derivatives
Direct Parent Gamma-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 Framework Aliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
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
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
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 GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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 Available
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CAS126-49-8
ChEBI29934
ChemSpider4573884
HMDBHMDB12283
IAF126034406
KEGGC00254
PubChem5460303