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Showing Compound Oleanolic acid (FDB013034)

Record Information
Version1.0
Creation date2010-04-08 22:10:29 UTC
Update date2019-11-26 03:07:54 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
MOLSDFPDBSMILESInChI
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Foods

Fats and oils:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSOleanolic acid, 2 TMS, GC-MS Spectrumsplash10-0udi-2951000000-3ffcf6404c28c9072e6eSpectrum
GC-MSOleanolic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-2951000000-3ffcf6404c28c9072e6eSpectrum
Predicted GC-MSOleanolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-0014900000-844b76f23b4a02a75c20Spectrum
Predicted GC-MSOleanolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1011190000-4d07cbb48cd57a724a3cSpectrum
Predicted GC-MSOleanolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0a4i-0000900002-a0a4b7ccad94baf5df672012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-0a4i-0000900000-bc55e4c6ed84a38ec6a82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0000900000-6a5c27def3e5639abbbc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0000900000-62f98aa71d39d7185d672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-0492f069e415506430f02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-09b6dab9027bd312a8162021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0001900000-948551e80a675e8049452017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vx-0116900000-a7bbd734cfb389f003ce2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-3459300000-fe5b4ff0a697d946a2052017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-24b5f92b17a675bd00422017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fu-0003900000-df302b7b4b1f9bf77cc52017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000e-2007900000-2e9882aa899cbe3bd6da2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-0d11296813b631a2140f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-a04074ef438068f127bb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0001900000-ec650846439f5cbbb4c22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-a2106bcf05d5c3dc7def2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0694700000-aa642e480c6b2dafc5d52021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ei-0940000000-67c9b141383d1a95ec292021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
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
Food Biomarker OntologyNot Available
VMH 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
AppleExpected but not quantifiedNot Available16448186
American cranberryExpected but not quantifiedNot AvailableDUKE
American pokeweedExpected but not quantifiedNot AvailableDUKE
BilberryExpected but not quantifiedNot AvailableDUKE
Black elderberryExpected but not quantifiedNot AvailableDUKE
Cloves1000.000 - 2000.000 mg/100 g1500.000 mg/100 gDUKE
Common grapeExpected but not quantifiedNot AvailableDUKE
Common oreganoExpected but not quantifiedNot AvailableDUKE
Common sage40.000 - 46.300 mg/100 g43.150 mg/100 gDUKE, KNAPSACK
Common thyme630.000 - 630.000 mg/100 g630.000 mg/100 gDUKE, KNAPSACK
Showing 1 to 10 of 68 entries
Biological Effects and Interactions
Health Effects / Bioactivities
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.