Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:10:29 UTC
Update date2018-05-29 01:02:39 UTC
Primary IDFDB013034
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameOleanolic acid
DescriptionOccurs as glycosides in cloves (Syzygium aromaticum), sugar beet (Beta vulgaris), olive leaves, etc. Very widely distributed aglycone Oleanolic acid or oleanic acid is a naturally occurring triterpenoid, widely distributed in food and medicinal plants, related to betulinic acid. It can be found in Phytolacca americana (American pokeweed), and Syzygium spp, garlic, etc. It is relatively non-toxic, antitumor, and hepatoprotective, as well as exhibiting antiviral properties.
CAS Number508-02-1
Structure
Thumb
Synonyms
SynonymSource
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 triterpenesHMDB
Triterpenes, oleananeHMDB
OleanolHMDB
HederinsHMDB
(+)-Oleanolic acidmanual
(3-beta)-3-Hydroxyolean-12-en-28-oatebiospider
(3-beta)-3-Hydroxyolean-12-en-28-oic acidbiospider
(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-oatebiospider
3-beta-Hydroxyolean-12-en-28-oic acidbiospider
3β-hydroxyolean-12-en-28-OateGenerator
3β-hydroxyolean-12-en-28-Oic acidGenerator
Gledigenin 1db_source
Olean-12-en-28-oic acid, 3-beta-hydroxy- (8CI)biospider
Olean-12-en-28-oic acid, 3-hydroxy-, (3-beta)-biospider
Olean-12-en-28-oic acid, 3-hydroxy-, (3β)-biospider
Olean-12-en-28-oic acid, 3β-hydroxy-biospider
Olean-12-en-28-oic acid, 3beta-hydroxy- (8CI)biospider
Oleanolic aciddb_source
Virgaureagenin Bdb_source
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H48O3
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
InChI IdentifierInChI=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
Isomeric SMILESCC1(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
Average Molecular Weight456.711
Monoisotopic Molecular Weight456.360345406
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointMp 306-308°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]12D +79.5 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0a4i-0000900002-a0a4b7ccad94baf5df67View 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
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID10062
ChEMBL IDCHEMBL168
KEGG Compound IDC17148
Pubchem Compound ID10494
Pubchem Substance IDNot Available
ChEBI ID37659
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02364
CRC / DFC (Dictionary of Food Compounds) IDKMF67-H:HNW57-L
EAFUS IDNot Available
Dr. Duke IDOLEANOLIC-ACID|BETA-OLEANOLIC-ACID
BIGG IDNot Available
KNApSAcK IDC00019064
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDOleanolic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
abortifacient50691 A chemical substance that interrupts pregnancy after implantation.DUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti arrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti atherosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti carcinomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti complementDUKE
anti edemicDUKE
anti fertilityDUKE
anti gingivitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti hyperlipidemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti ischemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti leukotriene35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti nephritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti periodonticDUKE
anti peroxidantDUKE
anti prostaglandin-E249023 A compound that inhibits the action of prostaglandins.DUKE
anti plaqueDUKE
anti plasmodial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti sarcomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti TGF-beta35222 A substance that diminishes the rate of a chemical reaction.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
aromatase inhibitor50790 An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.DUKE
beta-blockerDUKE
beta-glucuronidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardioprotective38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
elastase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hypolipemicDUKE
hypotensiveDUKE
immunomodulator50846 Biologically active substance whose activity affects or plays a role in the functioning of the immune system.DUKE
leucocytogenicDUKE
NF-kappa-B inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
phagocytoticDUKE
piscicideDUKE
prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
utero tonic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
vasopressorDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.