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Showing Compound Betulin (FDB015789)

Record Information
Version1.0
Creation date2010-04-08 22:12:03 UTC
Update date2019-11-26 03:12:13 UTC
Primary IDFDB015789
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBetulin
DescriptionConstituent of Corylus avellana (filbert) and Vicia faba Betulin (lup-20(29)-ene-3?,28-diol) is an abundant naturally occurring triterpene. It is commonly isolated from the bark of birch trees and forms up to 30% of the dry weight of the extractive. The purpose of the compound in the bark is not known. It can be converted to betulinic acid (the alcohol group replaced by a carboxylic acid group), which is biologically more active than betulin itself.; Chemically, betulin is a triterpenoid of lupane structure. It has a pentacyclic ring structure, and hydroxyl groups in positions C3 and C28. Betulin is found in many foods, some of which are common walnut, common sage, nuts, and common hazelnut.
CAS Number473-98-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3beta)-Lup-20(29)-ene-3,28-diolHMDB
BetulenolHMDB
BetulineHMDB
Betulinic alcoholHMDB
BetulinolHMDB
Betulinol (obsol.)HMDB
BetulolHMDB
Lup-20(29)-ene-3 beta,28-diolHMDB
Lup-20(29)-ene-3beta ,28-diolHMDB
Lup-20(29)-ene-3beta,28-diolHMDB
Lup-20(30)-ene-3beta ,28-diolHMDB
Lup-20(30)-ene-3beta,28-diolHMDB
MessageninHMDB
TrocholHMDB
Betulindb_source
Lup-20(29)-ene-3,28-diol, (3β)-biospider
Lup-20(29)-ene-3,28-diol, (3beta)-biospider
Lup-20(29)-ene-3β,28-diolbiospider
Lup-20(30)-ene-3β,28-diolbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.00032 g/LALOGPS
logP5.34ALOGPS
logP6.17ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)18.85ChemAxon
pKa (Strongest Basic)-0.65ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity132.68 m³·mol⁻¹ChemAxon
Polarizability54.76 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H50O2
IUPAC name5-(hydroxymethyl)-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol
InChI IdentifierInChI=1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3
InChI KeyFVWJYYTZTCVBKE-UHFFFAOYSA-N
Isomeric SMILESCC(=C)C1CCC2(CO)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C12
Average Molecular Weight442.7168
Monoisotopic Molecular Weight442.381080844
Classification
Description belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthraquinones
Direct ParentHydroxyanthraquinones
Alternative Parents
Substituents
  • Hydroxyanthraquinone
  • Cadinane sesquiterpenoid
  • Sesquiterpenoid
  • Tetralin
  • Quinone
  • Aryl alkyl ketone
  • Aryl ketone
  • Aryl-aldehyde
  • Vinylogous acid
  • Ketone
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aldehyde
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 81.39%; H 11.38%; O 7.23%DFC
Melting PointMp 251-252°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]15D +20 (Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-0123900000-c065f63cfc666ade1e12JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-1031190000-184b060ede0fa7d00f5fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0000900000-22e094b6986194d96d55JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0115900000-330f02ad90f1dc19ba92JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-3498100000-08dd583786c7a035765bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0000900000-22e094b6986194d96d55JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0115900000-330f02ad90f1dc19ba92JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-3498100000-08dd583786c7a035765bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0000900000-22e094b6986194d96d55JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0115900000-330f02ad90f1dc19ba92JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-3498100000-08dd583786c7a035765bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0000900000-22e094b6986194d96d55JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0115900000-330f02ad90f1dc19ba92JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-3498100000-08dd583786c7a035765bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-05ca0bd606f47edc98c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0001900000-f8147a299fc6f4a27886JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-2009800000-f3e02607e1649f1439c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-05ca0bd606f47edc98c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0001900000-f8147a299fc6f4a27886JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-2009800000-f3e02607e1649f1439c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-05ca0bd606f47edc98c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0001900000-f8147a299fc6f4a27886JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-2009800000-f3e02607e1649f1439c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-05ca0bd606f47edc98c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0001900000-f8147a299fc6f4a27886JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-2009800000-f3e02607e1649f1439c6JSpectraViewer
ChemSpider ID191735
ChEMBL IDNot Available
KEGG Compound IDC08618
Pubchem Compound ID221023
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36838
CRC / DFC (Dictionary of Food Compounds) IDJVB93-S:KJC50-N
EAFUS IDNot Available
Dr. Duke IDBETULIN
BIGG IDNot Available
KNApSAcK IDC00003740
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBetulin
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 carcinomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti feedantDUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
aphidifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
hypolipemicDUKE
prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.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— 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).