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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:08 UTC
HMDB IDHMDB0001023
Secondary Accession Numbers
  • HMDB0006924
  • HMDB01023
  • HMDB06924
Metabolite Identification
Common Name4,4-Dimethylcholesta-8,14,24-trienol
Description4,4-Dimethylcholesta-8,14,24-trienol is a product of the enzyme delta14-sterol reductase [EC 1.3.1.70] (KEGG). It is involved in the biosynthesis of steroids and is involved in the conversion of lanosterol to zymosterol. In particular, lanosterol 14-alpha-demethylase, catalyzes the C-14 demethylation of lanosterol to form 4,4-Dimethylcholesta-8,14,24-trienol in the ergosterol biosynthesis pathway. It is thought to be a meiosis activating sterol.
Structure
Thumb
Synonyms
ValueSource
4,4-Dimechol-8,14,24-trienolChEBI
4,4-Dimethylcholesta-8(9),14,24-trien-3beta-olChEBI
4,4-Dimethylcholesta-8(9),14,24-trien-3b-olGenerator
4,4-Dimethylcholesta-8(9),14,24-trien-3β-olGenerator
FF-MASMeSH
Follicular fluid meiosis activating sterolMeSH
4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3-olMeSH
(3beta,5alpha)-4,4-Dimethyl-cholesta-8,14,24-trien-3-olHMDB
(3beta,5alpha)-4,4-Dimethylcholesta-8,14,24-trien-3-olHMDB
4,4'-Dimethyl cholesta-8,14,24-triene-3-beta-olHMDB
4,4-Dimethyl-5-alpha-cholesta-8,14,24-trien-3-beta-olHMDB
4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3beta-olHMDB, MeSH
4,4-Dimethyl-cholesta-8,14,24-trienolHMDB
Chemical FormulaC29H46O
Average Molecular Weight410.6749
Monoisotopic Molecular Weight410.354866094
IUPAC Name(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
Traditional Name(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
CAS Registry Number64284-64-6
SMILES
C[C@H](CCC=C(C)C)[C@H]1CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3
InChI Identifier
InChI=1S/C29H46O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,13,20,22,25-26,30H,8,10-12,14-18H2,1-7H3/t20-,22-,25+,26+,28-,29-/m1/s1
InChI KeyLFQXEZVYNCBVDO-PBJLWWPKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen LocationsNot Available
Tissue Locations
  • Testis
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 IDFDB022376
KNApSAcK IDNot Available
Chemspider ID391478
KEGG Compound IDC11455
BioCyc IDNot Available
BiGG ID1454719
Wikipedia LinkNot Available
METLIN ID5952
PubChem Compound443212
PDB IDNot Available
ChEBI ID17813
Food Biomarker OntologyNot Available
VMH ID44MCTR
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceRuan B; Wilson W K; Schroepfer G J Jr An alternative synthesis of 4,4-dimethyl-5 alpha-cholesta-8,14,24-trien-3 beta-ol, an intermediate in sterol biosynthesis and a reported activator of meiosis and of nuclear orphan receptor LXR alpha. Bioorganic & medicinal chemistry letters (1998), 8(3), 233-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ruan B, Watanabe S, Eppig JJ, Kwoh C, Dzidic N, Pang J, Wilson WK, Schroepfer GJ Jr: Sterols affecting meiosis: novel chemical syntheses and the biological activity and spectral properties of the synthetic sterols. J Lipid Res. 1998 Oct;39(10):2005-20. [PubMed:9788247 ]

Enzymes

General function:
Involved in delta14-sterol reductase activity
Specific function:
Involved in the conversion of lanosterol to cholesterol.
Gene Name:
TM7SF2
Uniprot ID:
O76062
Molecular weight:
46405.345
Reactions
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADP → 4,4-Dimethylcholesta-8,14,24-trienol + NADPHdetails
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADP → 4,4-Dimethylcholesta-8,14,24-trienol + NADPH + Hydrogen Iondetails
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:
CYP51A1
Uniprot ID:
Q16850
Molecular weight:
57277.81
Reactions
Lanosterol + Oxygen + NADPH + Hydrogen Ion → 4,4-Dimethylcholesta-8,14,24-trienol + Formic acid + NADP + Waterdetails