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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:01:02 UTC
Update Date2021-10-13 06:59:21 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-triolHMDB
Lup-20(29)-ene-3alpha,28-diolHMDB
(+)-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
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
BetulinHMDB
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point251 - 252 °CNot Available
Boiling Point284.00 to 288.00 °C. @ 743.00 mm HgThe Good Scents Company Information System
Water Solubility0.00017 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP8.607 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00032 g/LALOGPS
logP10(5.34) g/LALOGPS
logP10(6.17) g/LChemAxon
logS10(-6.1) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Betulin[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)=C2561.0Standard polar33892256
Betulin[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)=C3513.8Standard non polar33892256
Betulin[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)=C3721.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Betulin,1TMS,isomer #1C=C(C)[C@@H]1CC[C@]2(CO[Si](C)(C)C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]123542.1Semi standard non polar33892256
Betulin,1TMS,isomer #2C=C(C)[C@@H]1CC[C@]2(CO)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]123571.4Semi standard non polar33892256
Betulin,2TMS,isomer #1C=C(C)[C@@H]1CC[C@]2(CO[Si](C)(C)C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]123487.1Semi standard non polar33892256
Betulin,1TBDMS,isomer #1C=C(C)[C@@H]1CC[C@]2(CO[Si](C)(C)C(C)(C)C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]123794.5Semi standard non polar33892256
Betulin,1TBDMS,isomer #2C=C(C)[C@@H]1CC[C@]2(CO)CC[C@]3(C)[C@H](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@]43C)[C@@H]123811.6Semi standard non polar33892256
Betulin,2TBDMS,isomer #1C=C(C)[C@@H]1CC[C@]2(CO[Si](C)(C)C(C)(C)C)CC[C@]3(C)[C@H](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@]43C)[C@@H]123996.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Betulin 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 - Betulin 40V, Positive-QTOFsplash10-0a4j-4900000000-dadc8ff785e95ea92f9c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulin 10V, Positive-QTOFsplash10-002f-0330900000-e409528990d47fe05f192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulin 20V, Positive-QTOFsplash10-02dl-2972300000-7e2de733d967ff2d37c02021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulin 10V, Positive-QTOFsplash10-004l-0000900000-d373a2e6f3eb26edab602017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulin 20V, Positive-QTOFsplash10-056r-0124900000-9051b1b6445c05333f522017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulin 40V, Positive-QTOFsplash10-014s-3296100000-e97b62b8178cdbc0dbe52017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulin 10V, Negative-QTOFsplash10-0006-0000900000-6b9c6b430f4d6f3668872017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulin 20V, Negative-QTOFsplash10-006x-0001900000-781f360759ec10b8a8762017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulin 40V, Negative-QTOFsplash10-01r5-2008900000-ff39cb4af6be09ad6a682017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulin 10V, Negative-QTOFsplash10-0006-0000900000-849799f7ece1fdb1b84b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulin 20V, Negative-QTOFsplash10-0006-0000900000-849799f7ece1fdb1b84b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulin 40V, Negative-QTOFsplash10-0006-0000900000-8e5df8e48f05e0b8285e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulin 10V, Positive-QTOFsplash10-0006-0004900000-7814a55372e37ae9ffc72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulin 20V, Positive-QTOFsplash10-0fbc-2697700000-08a961101a0c6748576f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulin 40V, Positive-QTOFsplash10-05di-9871000000-387e56fb36e1298aea922021-09-24Wishart 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 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 IDNot Available
Good Scents IDrw1012331
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.