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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:45 UTC
HMDB IDHMDB01023
Secondary Accession Numbers
  • 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
  1. (3beta,5alpha)-4,4-dimethyl-Cholesta-8,14,24-trien-3-ol
  2. (3beta,5alpha)-4,4-Dimethylcholesta-8,14,24-trien-3-ol
  3. 4,4'-Dimethyl cholesta-8,14,24-triene-3-beta-ol
  4. 4,4-Dimechol-8,14,24-trienol
  5. 4,4-Dimethyl-5-alpha-cholesta-8,14,24-trien-3-beta-ol
  6. 4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3-ol
  7. 4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol
  8. 4,4-Dimethyl-cholesta-8,14,24-trienol
  9. 4,4-Dimethylcholesta-8,14,24-trienol
  10. FF-MAS
  11. Follicular fluid meiosis activating sterol
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 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
CAS Registry Number64284-64-6
SMILES
[H][C@@]1(CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C
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
KingdomOrganic Compounds
Super ClassLipids
ClassPrenol Lipids
Sub ClassTriterpenes
Other Descriptors
  • 3beta-sterol(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • Cholesterol and derivatives(KEGG)
  • Cholesterol and derivatives(Lipidmaps)
Substituents
  • 3 Hydroxy Steroid
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Drimane Skeleton
  • Isoprene
  • Secondary Alcohol
  • Steroid
Direct ParentTriterpenes
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
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 Solubility0.001 g/LALOGPS
logP7.4ALOGPS
logP7ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity130.92ChemAxon
Polarizability52.91ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid LocationsNot Available
Tissue Location
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Steroid BiosynthesisSMP00023map00100
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022376
KNApSAcK IDNot Available
Chemspider ID391478
KEGG Compound IDC11455
BioCyc ID44-DIMETHYL-CHOLESTA-812-24-TRIENOL
BiGG ID1454719
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01023
Metagene LinkHMDB01023
METLIN ID5952
PubChem Compound443212
PDB IDNot Available
ChEBI ID17813
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
Lanosterin + Oxygen + NADPH + Hydrogen Ion → 4,4-Dimethylcholesta-8,14,24-trienol + Formic acid + NADP + Waterdetails