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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:51 UTC
Update Date2022-03-07 02:49:15 UTC
HMDB IDHMDB0002391
Secondary Accession Numbers
  • HMDB02391
Metabolite Identification
Common NameUvaol
DescriptionUvaol 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 ).
Structure
Data?1588356799
Synonyms
ValueSource
(3.beta.)-urs-12-ene-3,28-diolHMDB
(3beta)-Urs-12-ene-3,28-diolHMDB
Urs-12-ene-3,28-diolHMDB
Urs-12-ene-3beta,28-diolHMDB
Urs-12-ene-3 beta,28-diolHMDB
UvaolMeSH
Chemical FormulaC30H50O2
Average Molecular Weight442.728
Monoisotopic Molecular Weight442.38108085
IUPAC Name(3S,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-8a-(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
Traditional Nameuvaol
CAS Registry Number545-46-0
SMILES
[H][C@@]12[C@@H](C)[C@H](C)CC[C@]1(CO)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
InChI Identifier
InChI=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/t19-,20+,22+,23-,24+,25+,27+,28-,29-,30-/m1/s1
InChI KeyXUARCIYIVXVTAE-ZAPOICBTSA-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
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point523.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.0002 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP9.130 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability54.68 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
DeepCCS[M-2H]-238.13830932474
DeepCCS[M+Na]+212.38430932474
AllCCS[M+H]+211.832859911
AllCCS[M+H-H2O]+210.332859911
AllCCS[M+NH4]+213.232859911
AllCCS[M+Na]+213.632859911
AllCCS[M-H]-207.432859911
AllCCS[M+Na-2H]-209.432859911
AllCCS[M+HCOO]-211.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Uvaol[H][C@@]12[C@@H](C)[C@H](C)CC[C@]1(CO)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C2829.8Standard polar33892256
Uvaol[H][C@@]12[C@@H](C)[C@H](C)CC[C@]1(CO)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C3587.0Standard non polar33892256
Uvaol[H][C@@]12[C@@H](C)[C@H](C)CC[C@]1(CO)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C3737.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Uvaol,1TMS,isomer #1C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(CO[Si](C)(C)C)CC[C@H]1C3623.2Semi standard non polar33892256
Uvaol,1TMS,isomer #2C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(CO)CC[C@H]1C3644.9Semi standard non polar33892256
Uvaol,2TMS,isomer #1C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(CO[Si](C)(C)C)CC[C@H]1C3579.4Semi standard non polar33892256
Uvaol,1TBDMS,isomer #1C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(CO[Si](C)(C)C(C)(C)C)CC[C@H]1C3871.5Semi standard non polar33892256
Uvaol,1TBDMS,isomer #2C[C@@H]1[C@H]2C3=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@@]4(C)[C@]3(C)CC[C@@]2(CO)CC[C@H]1C3867.0Semi standard non polar33892256
Uvaol,2TBDMS,isomer #1C[C@@H]1[C@H]2C3=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@@]4(C)[C@]3(C)CC[C@@]2(CO[Si](C)(C)C(C)(C)C)CC[C@H]1C4081.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Uvaol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-0122900000-175477ab5c748536c9d72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Uvaol GC-MS (2 TMS) - 70eV, Positivesplash10-00di-1021190000-48704668226df9f3244d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Uvaol 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 - Uvaol Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-0006-0100900000-4a0d73fcef1863afc64a2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Uvaol Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0007-1920000000-d125a3fb0c728f5dbb402012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Uvaol Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-059b-5900000000-fd6e8a3360a0b0a720522012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uvaol 10V, Positive-QTOFsplash10-004l-0000900000-1b790f5e9eb5bf2bf90e2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uvaol 20V, Positive-QTOFsplash10-056r-1231900000-29ce819c5908fe6bde312017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uvaol 40V, Positive-QTOFsplash10-0pvj-7694100000-2b9064a475a1e08a9d512017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uvaol 10V, Negative-QTOFsplash10-0006-0000900000-7faf32cca5b2bea1eab22017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uvaol 20V, Negative-QTOFsplash10-006x-0001900000-ae3e9b87b7df659c36332017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uvaol 40V, Negative-QTOFsplash10-0005-1009600000-56d6425409f73e689b7c2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uvaol 10V, Positive-QTOFsplash10-0006-0001900000-28e870d4f02aa2fd80bf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uvaol 20V, Positive-QTOFsplash10-0f9f-0693500000-7540a7ec9759094ded0b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uvaol 40V, Positive-QTOFsplash10-009l-1950100000-018a3d754cb4bbca193e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uvaol 10V, Negative-QTOFsplash10-0006-0000900000-849799f7ece1fdb1b84b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uvaol 20V, Negative-QTOFsplash10-0006-0000900000-849799f7ece1fdb1b84b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uvaol 40V, Negative-QTOFsplash10-05g3-0001900000-abd852c3c467163ae2132021-09-22Wishart 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 LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013518
KNApSAcK IDC00032467
Chemspider ID83774
KEGG Compound IDNot Available
BioCyc IDCPD-14494
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92802
PDB IDNot Available
ChEBI ID519375
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1296251
References
Synthesis ReferenceZurcher, A.; Jeger, O.; Ruzicka, L. Triterpenes. CLXXX. The conversion of quinovaic acid to phyllanthol and uvaol. The constitution of ursolic acid and of uvaol. Helvetica Chimica Acta (1954), 37 2145-52.
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 ]