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Showing Compound Uvaol (FDB013518)

Record Information
Version1.0
Creation date2010-04-08 22:10:45 UTC
Update date2019-11-26 03:08:32 UTC
Primary IDFDB013518
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameUvaol
DescriptionConstituent of olive oil and Osmanthus fragrans (sweet osmanthus) Uvaol 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. Uvaol 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. (PMID: 17292619)
CAS Number545-46-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3.beta.)-urs-12-ene-3,28-diolHMDB
(3beta)-Urs-12-ene-3,28-diolbiospider
Urs-12-ene-3,28-diolbiospider
Urs-12-ene-3beta,28-diolbiospider
Uvaoldb_source
Predicted Properties
PropertyValueSource
Water Solubility0.00027 g/LALOGPS
logP6.13ALOGPS
logP6.11ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)18.95ChemAxon
pKa (Strongest Basic)-0.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity133.76 m³·mol⁻¹ChemAxon
Polarizability54.82 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H50O2
IUPAC name8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-ol
InChI IdentifierInChI=1S/C30H50O2/c1-19-10-15-30(18-31)17-16-28(6)21(25(30)20(19)2)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h8,19-20,22-25,31-32H,9-18H2,1-7H3
InChI KeyXUARCIYIVXVTAE-UHFFFAOYSA-N
Isomeric SMILESCC1CCC2(CO)CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C
Average Molecular Weight442.7168
Monoisotopic Molecular Weight442.381080844
Classification
DescriptionThis compound 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
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 81.39%; H 11.38%; O 7.23%DFC
Melting PointMp 232-233°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +70 (c, 0.93 in CHCl3)DFC
Spectroscopic UV Data[neutral] lmax 205 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0000900000-1b790f5e9eb5bf2bf90eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-1231900000-29ce819c5908fe6bde31JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvj-7694100000-2b9064a475a1e08a9d51JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-7faf32cca5b2bea1eab2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0001900000-ae3e9b87b7df659c3633JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-1009600000-56d6425409f73e689b7cJSpectraViewer
ChemSpider ID83774
ChEMBL IDCHEMBL399873
KEGG Compound IDNot Available
Pubchem Compound ID92802
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02391
CRC / DFC (Dictionary of Food Compounds) IDJFD07-X:JDW15-B
EAFUS IDNot Available
Dr. Duke IDUVAOL
BIGG IDNot Available
KNApSAcK IDC00032467
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
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 proliferativeDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).