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Record Information
Version3.6
Creation Date2012-09-11 19:33:10 UTC
Update Date2016-02-11 02:31:28 UTC
HMDB IDHMDB34655
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Epikatonic acid
Description3-Epikatonic acid is found in pulses. 3-Epikatonic acid is a constituent of Cyamopsis tetragonoloba (guar). 3-Epikatonic acid belongs to the family of Oleanane Triterpenes. These are triterpenes whose structure is based on the oleanane skeleton, an 4,4,6a,8a,11,11,14b-heptamethyl-hexadecahydropicene derivative.
Structure
Thumb
Synonyms
ValueSource
3-Hydroxy-(3beta,20alpha)-olean-12-en-29-Oic acidHMDB
Epikatonic acidHMDB
Chemical FormulaC30H48O3
Average Molecular Weight456.7003
Monoisotopic Molecular Weight456.360345402
IUPAC Name(2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid
Traditional Name(2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2-carboxylic acid
CAS Registry Number76035-62-6
SMILES
[H][C@@]12C[C@@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O
InChI Identifier
InChI=1/C30H48O3/c1-25(2)21-10-13-30(7)22(28(21,5)12-11-23(25)31)9-8-19-20-18-27(4,24(32)33)15-14-26(20,3)16-17-29(19,30)6/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,26+,27+,28-,29+,30+/s2
InChI KeyInChIKey=JZFSMVXQUWRSIW-NAKZPNCENA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as oleanane triterpenoids. These are triterpenoids with a structure based on the oleanane skeleton, an 4,4,6a,8a,11,14b-heptamethyl-hexadecahydropicene derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentOleanane triterpenoids
Alternative Parents
Substituents
  • Oleanane triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrient
Application
  • Nutrient
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point283 - 284 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00055 mg/mLALOGPS
logP7.19ALOGPS
logP6.59ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity133.62 m3·mol-1ChemAxon
Polarizability54.66 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB013179
KNApSAcK IDC00036544
Chemspider ID8609651
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB34655
Metagene LinkHMDB34655
METLIN IDNot Available
PubChem Compound10434225
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.