Record Information
Version1.0
Creation date2010-04-08 22:10:49 UTC
Update date2018-05-29 01:06:44 UTC
Primary IDFDB013641
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLupeol
DescriptionLupeol is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Lupeol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Lupeol can be found in a number of food items such as canola, wild carrot, annual wild rice, and european plum, which makes lupeol a potential biomarker for the consumption of these food products. Lupeol is a pharmacologically active triterpenoid. It has several potential medicinal properties .
CAS Number545-47-1
Structure
Thumb
Synonyms
SynonymSource
β-lupeolbiospider
β-viscolbiospider
1H-Cyclopenta[a]chrysene, lup-20(29)-en-3-ol deriv.biospider
b-Viscoldb_source
Cautchicoldb_source
Clerodoldb_source
Fagarasteroldb_source
Fagarsterolbiospider
Farganasterolbiospider
Lup-20(29)-en-3-olbiospider
Lup-20(29)-en-3-ol, (3β)-biospider
Lup-20(29)-en-3β-olbiospider
Lupenolbiospider
Lupeoldb_source
Monogynol Bdb_source
Triterpene lupeolbiospider
Xanthosterindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.00019 g/LALOGPS
logP5.97ALOGPS
logP7.45ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity130.91 m³·mol⁻¹ChemAxon
Polarizability53.8 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H50O
IUPAC name1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol
InChI IdentifierInChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3
InChI KeyMQYXUWHLBZFQQO-UHFFFAOYSA-N
Isomeric SMILESCC(=C)C1CCC2(C)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C12
Average Molecular Weight426.7174
Monoisotopic Molecular Weight426.386166222
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
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 84.44%; H 11.81%; O 3.75%DFC
Melting PointMp 215-216°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +26.4 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0011900000-5050c1fe6f79cc640e40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0579800000-bb52e352c147b0af98caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbj-2597100000-25942c8a036898062a7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-d739c6a879f3b6b778ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-a2c05f9b1d8dd849100dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1009500000-dc899db3dbe40f34e43eView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08628
Pubchem Compound ID259846
Pubchem Substance IDNot Available
ChEBI ID606123
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJFT17-C:JFT13-Y
EAFUS IDNot Available
Dr. Duke IDLUPEOL
BIGG IDNot Available
KNApSAcK IDC00003749
HET 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
anti angiogenic48422 An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.DUKE
anti Epstein-Barr virus22587 A substance that destroys or inhibits replication of viruses.DUKE
anti edemicDUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti hyperglycemicDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti lithicDUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti oxalateDUKE
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 peroxidantDUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti rheumatic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti urethroticDUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
FPTase 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
hypotensiveDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
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.