Showing Compound Card for Prephenate (CDB005029)

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Record Information
Version1.0
Created at2020-04-17 19:02:05 UTC
Updated at2020-11-18 16:39:13 UTC
CannabisDB IDCDB005029
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePrephenate
DescriptionPREPHENIC ACID, also known as cis-prephenate 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. A prephenic acid having (1s,4s)-cis-configuration. PREPHENIC ACID is an extremely weak basic (essentially neutral) compound (based on its pKa). Prephenate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight226.18
Monoisotopic Molecular Weight226.0477
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPrephenate, non-derivatized, GC-MS Spectrumsplash10-014u-6920000000-ef53f0db72ce3c5aa0c4Spectrum
Predicted GC-MSPrephenate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9610000000-b3ced3fa2b10936d8535Spectrum
Predicted GC-MSPrephenate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-0950000000-783758ab15df97a404b42017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bu9-1910000000-9f4b0bd1d617cf85c5b72017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-00e996c97c569d0bb94b2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1790000000-a8695b0e797b6ea4a6c72017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01sr-1920000000-f17d05344ee2d90f01c12017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-8900000000-b4238cbdb48e66836fb12017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a70-1970000000-7605a9b397a2136475b12021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07br-3900000000-1f4d611e994bbc1e075f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-97a22d2d646aceb138b72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-1960000000-3645029a13932992cfb02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dr-0900000000-317567c1da99c003ef6c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-4900000000-e8395b1eca4b111c28ce2021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0012283
DrugBank IDDB08427
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available