Record Information
Version1.0
Creation date2010-04-08 22:10:49 UTC
Update date2025-11-19 00:22:13 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 Solubility0.0002 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
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
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLupeol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dj-0119400000-544f7e1713d3a6d84864Spectrum
Predicted GC-MSLupeol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLupeol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLupeol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0011900000-5050c1fe6f79cc640e402016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0579800000-bb52e352c147b0af98ca2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbj-2597100000-25942c8a036898062a7a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-d739c6a879f3b6b778eb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-a2c05f9b1d8dd849100d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1009500000-dc899db3dbe40f34e43e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0004900000-ae22da79c014597e85062021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-055r-2790300000-09360cec56fad60faf462021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053i-4942000000-207dff202d58aa0746852021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-590c9e4adfdd12b64d932021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-590c9e4adfdd12b64d932021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0000900000-390655f1ec092e7b75172021-10-12View Spectrum
NMRNot Available
ChemSpider ID454916
ChEMBL IDCHEMBL3188790
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
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLupeol
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 that inhibits the formation of new blood vessels, playing a crucial role in cancer treatment by starving tumors of oxygen and nutrients. Therapeutically, it is used to manage cancer, age-related macular degeneration, and other diseases characterized by excessive angiogenesis, reducing tumor growth and slowing disease progression.DUKE
Anti Epstein-Barr virus22587 An agent that targets and neutralizes the Epstein-Barr virus, reducing its replication and associated diseases, such as infectious mononucleosis and certain types of cancer, with therapeutic applications in immunocompromised patients and key medical uses in preventing and treating EBV-related disorders.DUKE
Anti-edemicAn agent that relieves or prevents edema, reducing abnormal fluid accumulation in tissues or the circulatory system, commonly used to treat conditions such as swelling, inflammation, and water retention.DUKE
Anti-flu22587 An agent that prevents or treats influenza virus infections, reducing symptoms and complications. Its biological role involves blocking viral replication, and its therapeutic applications include prophylaxis and treatment of flu outbreaks. Key medical uses include reducing the risk of flu-related hospitalizations and mortality, especially in high-risk populations such as the elderly and young children.DUKE
Anti hyperglycemicAn agent that lowers elevated blood glucose levels, playing a crucial biological role in regulating glucose metabolism. Therapeutically, it is used to manage hyperglycemia, with key medical applications in treating diabetes mellitus, reducing the risk of complications, and improving glycemic control.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-lithicAn agent that prevents the formation of calculi (kidney stones) or promotes their dissolution, playing a key role in urology. Its therapeutic applications include managing kidney stone disease, nephrolithiasis, and urinary tract disorders, helping to alleviate pain and prevent complications.DUKE
Anti-malarial33281 An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis.DUKE
Anti-oxalateAn agent that reduces oxalate levels, used to prevent kidney stone formation and manage hyperoxaluria, a condition characterized by excessive oxalate production, often associated with kidney damage and disease.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti peroxidantAn agent that prevents oxygen atom and peroxide formation, reducing oxidative stress and cell damage. It plays a biological role in protecting cells from free radicals. Therapeutically, it's used to manage conditions like cancer, Alzheimer's, and atherosclerosis, with key medical applications in neuroprotection, cardiovascular health, and anti-aging.DUKE
Anti prostaglandin49020 An agent that inhibits prostaglandin production, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and post-surgical pain, by blocking prostaglandin-mediated responses, providing relief from inflammation and discomfort.DUKE
Anti-rheumatic52217 An agent that reduces inflammation and alleviates symptoms of rheumatic diseases, such as arthritis. It plays a biological role in modulating the immune system and inhibiting pro-inflammatory pathways. Therapeutically, anti-rheumatics are used to manage conditions like rheumatoid arthritis, lupus, and osteoarthritis, reducing pain, swelling, and joint damage. Key medical uses include slowing disease progression and improving quality of life for patients with chronic rheumatic conditions.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Anti urethroticAn agent that relieves inflammation of the urethra, playing a role in reducing discomfort and pain. Therapeutically, it is used to treat urethral irritation and inflammation, with key medical applications in managing urethritis, urinary tract infections, and post-procedural urethral trauma.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
FPTase inhibitor23924 An agent that blocks the activity of farnesyl protein transferase (FPTase), an enzyme involved in cancer cell growth. It has therapeutic applications in oncology, particularly in treating certain types of cancer, such as pancreatic and lung cancer, by inhibiting tumor growth and proliferation.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Topoisomerase-II inhibitor50750 An agent that blocks the activity of topoisomerase-II, an enzyme involved in DNA replication. It prevents cancer cell growth by disrupting DNA structure, commonly used in chemotherapy to treat various types of cancer, including leukemia and lymphoma.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.