Showing metabocard for Oleanolic acid (BMDB0002364)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:54:37 UTC
Update Date2020-04-22 15:10:48 UTC
BMDB IDBMDB0002364
Secondary Accession Numbers
  • BMDB02364
Metabolite Identification
Common NameOleanolic acid
DescriptionOleanolic acid, also known as astrantiagenin C or caryophyllin, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review a significant number of articles have been published on Oleanolic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3beta-Hydroxyolean-12-en-28-Oic acidChEBI
Astrantiagenin CChEBI
CaryophyllinChEBI
Giganteumgenin CChEBI
Oleanic acidChEBI
Virgaureagenin bChEBI
OleanolateKegg
3b-Hydroxyolean-12-en-28-OateGenerator
3b-Hydroxyolean-12-en-28-Oic acidGenerator
3beta-Hydroxyolean-12-en-28-OateGenerator
3Β-hydroxyolean-12-en-28-OateGenerator
3Β-hydroxyolean-12-en-28-Oic acidGenerator
OleanateGenerator
(3-beta)-3-Hydroxyolean-12-en-28-oateHMDB
(3-beta)-3-Hydroxyolean-12-en-28-oic acidHMDB
(3.beta.)-3-beta-hydroxy-olean-12-en-28-oateHMDB
(3.beta.)-3-beta-hydroxy-olean-12-en-28-oic acidHMDB
(3.beta.)-3-hydroxy-olean-12-en-28-oateHMDB
(3.beta.)-3-hydroxy-olean-12-en-28-oic acidHMDB
(4AS,5S,6as,6BR,8R,8ar,10S,12ar,12BR,14BS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acidHMDB
3-beta-Hydroxyolean-12-en-28-oateHMDB
3-beta-Hydroxyolean-12-en-28-oic acidHMDB
3.beta.-hydroxy-olean-12-en-28-oateHMDB
3.beta.-hydroxy-olean-12-en-28-oic acidHMDB
3beta-Hydroxy-olean-12-en-28-oateHMDB
3beta-Hydroxy-olean-12-en-28-oic acidHMDB
Oleanane triterpenesMeSH, HMDB
Triterpenes, oleananeMeSH, HMDB
OleanolMeSH, HMDB
HederinsMeSH, HMDB
(3beta)-3-Hydroxyolean-12-en-28-oic acidPhytoBank
(3β)-3-Hydroxyolean-12-en-28-oic acidPhytoBank
(+)-Oleanolic acidPhytoBank
Gledigenin 1PhytoBank
Oleonolic acidPhytoBank
OAPhytoBank
Chemical FormulaC30H48O3
Average Molecular Weight456.711
Monoisotopic Molecular Weight456.360345406
IUPAC Name(4aS,6aS,6bR,8aR,10S,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 Nameoleanolic acid
CAS Registry Number508-02-1
SMILES
CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(O)=O
InChI Identifier
InChI=1S/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-/m0/s1
InChI KeyMIJYXULNPSFWEK-GTOFXWBISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point310 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity133.62 m³·mol⁻¹ChemAxon
Polarizability54.87 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-2951000000-3ffcf6404c28c9072e6eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-2951000000-3ffcf6404c28c9072e6eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-0014900000-844b76f23b4a02a75c20View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000i-1011190000-4d07cbb48cd57a724a3cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0a4i-0000900002-a0a4b7ccad94baf5df67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-0a4i-0000900000-bc55e4c6ed84a38ec6a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0000900000-6a5c27def3e5639abbbcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0000900000-62f98aa71d39d7185d67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-0492f069e415506430f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-09b6dab9027bd312a816View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0001900000-948551e80a675e804945View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vx-0116900000-a7bbd734cfb389f003ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-3459300000-fe5b4ff0a697d946a205View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-24b5f92b17a675bd0042View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fu-0003900000-df302b7b4b1f9bf77cc5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000e-2007900000-2e9882aa899cbe3bd6daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-0d11296813b631a2140fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-a04074ef438068f127bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0001900000-ec650846439f5cbbb4c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-a2106bcf05d5c3dc7defView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0694700000-aa642e480c6b2dafc5d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ei-0940000000-67c9b141383d1a95ec29View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002364
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013034
KNApSAcK IDC00019064
Chemspider ID10062
KEGG Compound IDC17148
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOleanolic_acid
METLIN IDNot Available
PubChem Compound10494
PDB IDNot Available
ChEBI ID37659
References
Synthesis ReferenceCorey, E. J.; Lee, Jaemoon. Enantioselective total synthesis of oleanolic acid, erythrodiol, b-amyrin, and other pentacyclic triterpenes from a common intermediate. Journal of the American Chemical Society (1993), 115(19), 8873-4.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available