Showing metabocard for Prephenate (BMDB0012283)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:35:31 UTC
Update Date2020-04-22 15:49:28 UTC
BMDB IDBMDB0012283
Secondary Accession Numbers
  • BMDB12283
Metabolite Identification
Common NamePrephenate
DescriptionPrephenate, also known as prephenic acid or prephenate, cis, 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. Based on a literature review a significant number of articles have been published on Prephenate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
cis-1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acidChEBI
cis-Prephenic acidChEBI
Prephenic acid, cisChEBI
Prephenic acidKegg
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
(1S,4S)-PrephenateHMDB
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
PrephenateGenerator
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 Number126-49-8
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
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
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014u-6920000000-ef53f0db72ce3c5aa0c4View 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 (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-0950000000-783758ab15df97a404b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bu9-1910000000-9f4b0bd1d617cf85c5b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-00e996c97c569d0bb94bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1790000000-a8695b0e797b6ea4a6c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01sr-1920000000-f17d05344ee2d90f01c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-8900000000-b4238cbdb48e66836fb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a70-1970000000-7605a9b397a2136475b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07br-3900000000-1f4d611e994bbc1e075fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-97a22d2d646aceb138b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-1960000000-3645029a13932992cfb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dr-0900000000-317567c1da99c003ef6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-4900000000-e8395b1eca4b111c28ceView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012283
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available