Human Metabolome Database Version 3.5

Showing metabocard for 4,4-Dimethylcholesta-8,14,24-trienol (HMDB01023)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:45 -0700
HMDB ID HMDB01023
Secondary Accession Numbers
  • HMDB06924
Metabolite Identification
Common Name 4,4-Dimethylcholesta-8,14,24-trienol
Description 4,4-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C29H46O
Average Molecular Weight 410.6749
Monoisotopic Molecular Weight 410.354866094
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 Number 64284-64-6
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 Key LFQXEZVYNCBVDO-PBJLWWPKSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Triterpenes
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 Parent Triterpenes
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.001 g/L ALOGPS
LogP 7.40 ALOGPS
LogP 7 ChemAxon
LogS -5.61 ALOGPS
pKa (strongest acidic) 19.55 ChemAxon
pKa (strongest basic) -0.81 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 130.92 ChemAxon
Polarizability 52.91 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations Not Available
Tissue Location
  • Testes
Pathways
Name SMPDB Link KEGG Link
Steroid Biosynthesis SMP00023 map00100 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022376
KNApSAcK ID Not Available
Chemspider ID 391478 Link_out
KEGG Compound ID C11455 Link_out
BioCyc ID 44-DIMETHYL-CHOLESTA-812-24-TRIENOL Link_out
BiGG ID 1454719 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB01023 Link_out
Metagene Link HMDB01023 Link_out
METLIN ID 5952 Link_out
PubChem Compound 443212 Link_out
PDB ID Not Available
ChEBI ID 17813 Link_out
References
Synthesis Reference Ruan 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 Link_out

Enzymes
Name: Delta(14)-sterol reductase
Reactions:
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADP unknown 4,4-Dimethylcholesta-8,14,24-trienol + NADPH details
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADP unknown 4,4-Dimethylcholesta-8,14,24-trienol + NADPH + Hydrogen Ion details
Gene Name: TM7SF2
Uniprot ID: O76062 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lanosterol 14-alpha demethylase
Reactions:
Lanosterin + Oxygen + NADPH + Hydrogen Ion unknown 4,4-Dimethylcholesta-8,14,24-trienol + Formic acid + NADP + Water details
Gene Name: CYP51A1
Uniprot ID: Q16850 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA