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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:58:41 UTC
Update Date2019-07-23 06:19:54 UTC
HMDB IDHMDB0035930
Secondary Accession Numbers
  • HMDB35930
Metabolite Identification
Common Namegamma-Taraxastane-3,20-diol
Descriptiongamma-Taraxastane-3,20-diol, also known as 3,5-dibromo-L-tyrosine or biotiren, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. gamma-Taraxastane-3,20-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862794
Synonyms
ValueSource
g-Taraxastane-3,20-diolGenerator
Γ-taraxastane-3,20-diolGenerator
3,5-Dibromo-4-hydroxyphenylalanineHMDB
3,5-Dibromo-L-tyrosineHMDB
3,5-Dibromo-tyrosineHMDB
3,5-DibromotyrosineHMDB
BiotirenHMDB
BromotirenHMDB
DBTHMDB
DibromotirinaHMDB
DibromotyrosineHMDB
Y-taraxastane-3,20-diolHMDB
Chemical FormulaC30H52O2
Average Molecular Weight444.7327
Monoisotopic Molecular Weight444.396730908
IUPAC Name1,2,4a,6a,6b,9,9,12a-octamethyl-docosahydropicene-2,10-diol
Traditional Name1,2,4a,6a,6b,9,9,12a-octamethyl-hexadecahydropicene-2,10-diol
CAS Registry Number10376-47-3
SMILES
CC1C2C3CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C)CCC1(C)O
InChI Identifier
InChI=1S/C30H52O2/c1-19-24-20-9-10-22-27(5)13-12-23(31)25(2,3)21(27)11-14-29(22,7)28(20,6)17-15-26(24,4)16-18-30(19,8)32/h19-24,31-32H,9-18H2,1-8H3
InChI KeyFDNWHCZIHBJRLP-UHFFFAOYSA-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
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point270 - 272 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.6e-05 g/LALOGPS
logP5.55ALOGPS
logP6.48ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.49ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity132.81 m³·mol⁻¹ChemAxon
Polarizability55.22 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-016r-0125900000-3d6176d63a0466b51b30Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-0021290000-a132446399a4024c9bddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0000900000-e9d7cb768f34a250ab07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0225900000-0bfb2bd29ced74936e13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-0559300000-c0cdcfcdd6bcc017c52fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0000900000-e9d7cb768f34a250ab07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0225900000-0bfb2bd29ced74936e13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-0559300000-c0cdcfcdd6bcc017c52fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-5ca83a92d4e9fe4f8886Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-0000900000-29065b1e308ec8c79d5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-1002900000-7ef737cce20121a8314cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-5ca83a92d4e9fe4f8886Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-0000900000-29065b1e308ec8c79d5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-1002900000-7ef737cce20121a8314cSpectrum
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 IDFDB014732
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14313597
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.