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Record Information
Version3.6
Creation Date2012-09-11 22:11:57 UTC
Update Date2016-02-11 02:44:36 UTC
HMDB IDHMDB36962
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Epioleanolic acid
Description3-Epioleanolic acid is found in common sage. 3-Epioleanolic acid is isolated from sage Salvia officinalis and other plants.
Structure
Thumb
Synonyms
ValueSource
Epi-oleanolic acidChEMBL
3-Epioleanolic acidChEMBL
Epi-oleanolateGenerator
(4As,6as,6BR,8ar,10R,12ar,12BR,14BS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylateGenerator
3-EpioleanolateGenerator
3-alpha-Hydroxyolean-12-en-28-OateHMDB
3-alpha-Hydroxyolean-12-en-28-Oic acidHMDB
Chemical FormulaC30H48O3
Average Molecular Weight456.7003
Monoisotopic Molecular Weight456.360345402
IUPAC Name(4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-10-hydroxy-2,2,6a,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-4a-carboxylic acid
Traditional Name(4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid
CAS Registry Number25499-90-5
SMILES
[H][C@@]12CC(C)(C)CC[C@@]1(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)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23+,27-,28+,29+,30-/s2
InChI KeyInChIKey=MIJYXULNPSFWEK-XBSYWBQYNA-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 Point297 - 299 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000817 mg/mLALOGPS
logP7.09ALOGPS
logP6.59ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.74ChemAxon
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
Polarizability54.61 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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 IDFDB015933
KNApSAcK IDC00029494
Chemspider ID10043989
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB36962
Metagene LinkHMDB36962
METLIN IDNot Available
PubChem Compound11869658
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Caldwell CG, Franzblau SG, Suarez E, Timmermann BN: Oleanane triterpenes from Junellia tridens. J Nat Prod. 2000 Dec;63(12):1611-4. [11141098 ]
  2. Deepak M, Handa SS: Antiinflammatory activity and chemical composition of extracts of Verbena officinalis. Phytother Res. 2000 Sep;14(6):463-5. [10960904 ]
  3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.