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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2022-03-07 02:49:15 UTC
HMDB IDHMDB0002364
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 ).
Structure
Data?1601232706
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
[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=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
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point310 °CNot Available
Boiling Point553.00 to 554.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.0017 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP8.576 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00082 g/LALOGPS
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+205.70831661259
DarkChem[M-H]-197.38831661259
DeepCCS[M-2H]-232.01230932474
DeepCCS[M+Na]+206.36230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Oleanolic acid[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)=O3223.1Standard polar33892256
Oleanolic acid[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)=O3628.5Standard non polar33892256
Oleanolic acid[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)=O3683.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oleanolic acid,1TMS,isomer #1CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C13725.7Semi standard non polar33892256
Oleanolic acid,1TMS,isomer #2CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C13618.0Semi standard non polar33892256
Oleanolic acid,2TMS,isomer #1CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C13591.4Semi standard non polar33892256
Oleanolic acid,1TBDMS,isomer #1CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C13953.4Semi standard non polar33892256
Oleanolic acid,1TBDMS,isomer #2CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C13887.1Semi standard non polar33892256
Oleanolic acid,2TBDMS,isomer #1CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C14090.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Oleanolic acid GC-MS (2 TMS)splash10-0udi-2951000000-3ffcf6404c28c9072e6e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oleanolic acid GC-MS (Non-derivatized)splash10-0udi-2951000000-3ffcf6404c28c9072e6e2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleanolic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-0014900000-844b76f23b4a02a75c202017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleanolic acid GC-MS (2 TMS) - 70eV, Positivesplash10-000i-1011190000-4d07cbb48cd57a724a3c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleanolic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleanolic acid LC-ESI-ITTOF (LCMS-IT-TOF) , Negative-QTOFsplash10-0a4i-0000900002-a0a4b7ccad94baf5df672012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleanolic acid 50V, Negative-QTOFsplash10-0a4i-0000900000-bc55e4c6ed84a38ec6a82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleanolic acid 40V, Negative-QTOFsplash10-0a4i-0000900000-6a5c27def3e5639abbbc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleanolic acid 30V, Negative-QTOFsplash10-0a4i-0000900000-62f98aa71d39d7185d672021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleanolic acid 10V, Negative-QTOFsplash10-0a4i-0000900000-0492f069e415506430f02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleanolic acid 20V, Negative-QTOFsplash10-0a4i-0000900000-09b6dab9027bd312a8162021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleanolic acid 10V, Positive-QTOFsplash10-052r-0001900000-948551e80a675e8049452017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleanolic acid 20V, Positive-QTOFsplash10-01vx-0116900000-a7bbd734cfb389f003ce2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleanolic acid 40V, Positive-QTOFsplash10-001l-3459300000-fe5b4ff0a697d946a2052017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleanolic acid 10V, Negative-QTOFsplash10-0a4i-0000900000-24b5f92b17a675bd00422017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleanolic acid 20V, Negative-QTOFsplash10-08fu-0003900000-df302b7b4b1f9bf77cc52017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleanolic acid 40V, Negative-QTOFsplash10-000e-2007900000-2e9882aa899cbe3bd6da2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleanolic acid 10V, Negative-QTOFsplash10-0a4i-0000900000-0d11296813b631a2140f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleanolic acid 20V, Negative-QTOFsplash10-0a4i-0000900000-a04074ef438068f127bb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleanolic acid 40V, Negative-QTOFsplash10-0a4i-0001900000-ec650846439f5cbbb4c22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleanolic acid 10V, Positive-QTOFsplash10-0a4i-0000900000-a2106bcf05d5c3dc7def2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleanolic acid 20V, Positive-QTOFsplash10-052r-0694700000-aa642e480c6b2dafc5d52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleanolic acid 40V, Positive-QTOFsplash10-00ei-0940000000-67c9b141383d1a95ec292021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
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
Good Scents IDrw1270801
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)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 ]