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Record Information
StatusDetected and Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2021-09-14 15:41:43 UTC
Secondary Accession Numbers
  • HMDB02364
Metabolite Identification
Common NameOleanolic acid
DescriptionOleanolic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Oleanolic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. Oleanolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. (PMID:17292619 , 15522132 , 15994040 ).
3beta-Hydroxyolean-12-en-28-Oic acidChEBI
Astrantiagenin CChEBI
Giganteumgenin CChEBI
Oleanic acidChEBI
Virgaureagenin bChEBI
3b-Hydroxyolean-12-en-28-Oic acidGenerator
3Β-hydroxyolean-12-en-28-Oic acidGenerator
(3-beta)-3-Hydroxyolean-12-en-28-Oic acidHMDB
(3.beta.)-3-beta-hydroxy-olean-12-en-28-Oic acidHMDB
(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-Oic acidHMDB
3.beta.-hydroxy-olean-12-en-28-Oic acidHMDB
3beta-Hydroxy-olean-12-en-28-Oic acidHMDB
Oleanane triterpenesHMDB
Triterpenes, oleananeHMDB
(3beta)-3-Hydroxyolean-12-en-28-oic acidPhytoBank
(3β)-3-Hydroxyolean-12-en-28-oic acidPhytoBank
(+)-Oleanolic acidPhytoBank
Gledigenin 1PhytoBank
Oleonolic acidPhytoBank
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
InChI Identifier
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
  • 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

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting Point310 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.00082 g/LALOGPS
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
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon


Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-2951000000-3ffcf6404c28c9072e6e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-2951000000-3ffcf6404c28c9072e6e2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-0014900000-844b76f23b4a02a75c202017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000i-1011190000-4d07cbb48cd57a724a3c2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-002f-0023900000-56b699a28dcac02b81212021-09-05View Spectrum


Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0a4i-0000900002-a0a4b7ccad94baf5df672012-08-31View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0001900000-948551e80a675e8049452017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vx-0116900000-a7bbd734cfb389f003ce2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-3459300000-fe5b4ff0a697d946a2052017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-24b5f92b17a675bd00422017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fu-0003900000-df302b7b4b1f9bf77cc52017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000e-2007900000-2e9882aa899cbe3bd6da2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-0d11296813b631a2140f2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-a04074ef438068f127bb2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0001900000-ec650846439f5cbbb4c22021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-a2106bcf05d5c3dc7def2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0694700000-aa642e480c6b2dafc5d52021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ei-0940000000-67c9b141383d1a95ec292021-09-07View Spectrum


Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)2012-12-05View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, 100%_DMSO, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodDetected and Quantified0.026 +/- 0.014 uMAdult (>18 years old)MaleNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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)Download (PDF)
General References
  1. Marquez-Martin A, De La Puerta R, Fernandez-Arche A, Ruiz-Gutierrez V, Yaqoob P: Modulation of cytokine secretion by pentacyclic triterpenes from olive pomace oil in human mononuclear cells. Cytokine. 2006 Dec;36(5-6):211-7. Epub 2007 Feb 9. [PubMed:17292619 ]
  2. Rodriguez-Rodriguez R, Herrera MD, Perona JS, Ruiz-Gutierrez V: Potential vasorelaxant effects of oleanolic acid and erythrodiol, two triterpenoids contained in 'orujo' olive oil, on rat aorta. Br J Nutr. 2004 Oct;92(4):635-42. [PubMed:15522132 ]
  3. Liu J: Oleanolic acid and ursolic acid: research perspectives. J Ethnopharmacol. 2005 Aug 22;100(1-2):92-4. [PubMed:15994040 ]