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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:01:02 UTC
Update Date2020-09-17 18:43:16 UTC
HMDB IDHMDB0036838
Secondary Accession Numbers
  • HMDB36838
Metabolite Identification
Common NameBetulin
DescriptionBetulin is found in black elderberry. Betulin is a constituent 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
Structure
Data?1600368196
Synonyms
ValueSource
BetulineChEBI
BetulinolChEBI
BetulolChEBI
TrocholChEBI
Lup-20(29)-en-3 alpha, 28,30-triolMeSH
Lup-20(29)-ene-3alpha,28-diolMeSH
(+)-BetulinHMDB
(3beta)-Lup-20(29)-ene-3,28-diolHMDB
(3β)-Lup-20(29)-ene-3,28-diolHMDB
3,28-Dihydroxy-lupeolHMDB
3beta,28-Dihydroxylup-20(29)-eneHMDB
3β,28-Dihydroxylup-20(29)-eneHMDB
BetulinHMDB
Betulinic alcoholHMDB
Lup-20(29)-ene-3beta,28-diolHMDB
Lup-20(29)-ene-3β,28-diolHMDB
Lup-20(30)-ene-3beta,28-diolHMDB
Lup-20(30)-ene-3β,28-diolHMDB
Chemical FormulaC30H50O2
Average Molecular Weight442.728
Monoisotopic Molecular Weight442.38108085
IUPAC Name(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-5-(hydroxymethyl)-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-ol
Traditional Name(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-5-(hydroxymethyl)-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-ol
CAS Registry Number473-98-3
SMILES
[H][C@]12[C@@H](CC[C@]1(CO)CC[C@]1(C)[C@]2([H])CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(C)=C
InChI Identifier
InChI=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/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
InChI KeyFVWJYYTZTCVBKE-ROUWMTJPSA-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
  • 18-hydroxysteroid
  • Hydroxysteroid
  • Steroid
  • 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

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point251 - 252 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Polarizability54.72 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0000900000-d373a2e6f3eb26edab60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0124900000-9051b1b6445c05333f52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014s-3296100000-e97b62b8178cdbc0dbe5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-6b9c6b430f4d6f366887Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0001900000-781f360759ec10b8a876Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r5-2008900000-ff39cb4af6be09ad6a68Spectrum
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 IDFDB015789
KNApSAcK IDC00003740
Chemspider ID65272
KEGG Compound IDC08618
BioCyc IDCPD-14491
BiGG IDNot Available
Wikipedia LinkBetulin
METLIN IDNot Available
PubChem Compound72326
PDB IDNot Available
ChEBI ID3086
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Flekhter OB, Medvedeva NI, Tolstikov GA, Galin FZ, Iunusov MS, Huong NT, Le VT, Svinova OV, Boreko EI, Titov LP, Glukhov IV: [Synthesis of olean-18(19)-ene derivatives from betulin]. Bioorg Khim. 2009 Mar-Apr;35(2):253-9. [PubMed:19537177 ]
  2. Lin YC, Cheng HY, Huang TH, Huang HW, Lee YH, Peng WH: Analgesic and anti-inflammatory activities of Torenia concolor Lindley var. formosana Yamazaki and betulin in mice. Am J Chin Med. 2009;37(1):97-111. [PubMed:19222115 ]
  3. Rzeski W, Stepulak A, Szymanski M, Juszczak M, Grabarska A, Sifringer M, Kaczor J, Kandefer-Szerszen M: Betulin elicits anti-cancer effects in tumour primary cultures and cell lines in vitro. Basic Clin Pharmacol Toxicol. 2009 Dec;105(6):425-32. doi: 10.1111/j.1742-7843.2009.00471.x. Epub 2009 Oct 12. [PubMed:19821831 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.