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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:24 UTC
Update Date2020-02-26 21:37:03 UTC
HMDB IDHMDB0012171
Secondary Accession Numbers
  • HMDB12171
Metabolite Identification
Common Name4alpha-Hydroxymethyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol
Description4alpha-hydroxymethyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis II (via 24,25-dihydrolanosterol). It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic reduction of 4alpha-formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol or from the enzymatic oxidation of 4,4-dimethyl-5alpha-cholesta-8-en-3-beta-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.
Structure
Data?1582753023
Synonyms
ValueSource
4a-Hydroxymethyl-4b-methyl-5a-cholesta-8-en-3b-olGenerator
4Α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-olGenerator
4a-Hydroxymethyl-4beta-methyl-5a-cholesta-8-en-3beta-olHMDB
4alpha-Hydroxymethyl-4b-methyl-5alpha-cholesta-8-en-3b-olHMDB
Chemical FormulaC29H50O2
Average Molecular Weight430.7061
Monoisotopic Molecular Weight430.381080844
IUPAC Name(2S,5S,6R,15R)-6-(hydroxymethyl)-2,6,15-trimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,6R,15R)-6-(hydroxymethyl)-2,6,15-trimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
CAS Registry NumberNot Available
SMILES
CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(CO)C1CC3
InChI Identifier
InChI=1S/C29H50O2/c1-19(2)8-7-9-20(3)22-11-12-23-21-10-13-25-28(5,24(21)14-16-27(22,23)4)17-15-26(31)29(25,6)18-30/h19-20,22-23,25-26,30-31H,7-18H2,1-6H3/t20?,22?,23?,25?,26-,27+,28+,29-/m0/s1
InChI KeyUVSRXDFMOZKKGE-AEWFMJFUSA-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
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0011 g/LALOGPS
logP6.29ALOGPS
logP6.53ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)14.49ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity130.99 m³·mol⁻¹ChemAxon
Polarizability55.07 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0i00-3016900000-ab3e529fef0b0b6bc74cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-08fs-3101390000-e98dc85fd15b3dfd4259Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0003900000-859fa2e6192485c5f81dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fs-4139600000-0587ba2fd78141207947Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-6539300000-3007858fd17a652e7f22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0001900000-c1917f0711e0ae853c69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01u1-0008900000-09a21da797853708753cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0009000000-57a536ae23b1dd6fca8bSpectrum
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 IDFDB028825
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25203709
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.