Fri. Sep 6th, 2024

4,4-Dimethylcholesta-8,14,24-trienol

By rofalproject
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 particliar, 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 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 (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-3-olHMDB 4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3beta-olHMDB 4,4-Dimethyl-cholesta-8,14,24-trienolHMDB FF-MASHMDB Follicliar fluid meiosis activating sterolHMDB

Chemical Formlia

C29H46O Average Molecliar Weight

410.6749 Monoisotopic Molecliar Weight

410.354866094 IUPAC Name

(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),11-dien-5-ol Traditional Name

FF-mas 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 Classification

Not classified Ontology Status

Expected but 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 Emlisifiers

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane (predicted from logP)
  • Endoplasmic reticlium

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.001 mg/mLALOGPS 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 Area20.23 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity130.92 m3·mol-1ChemAxon Polarizability52.91 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Membrane (predicted from logP)
  • Endoplasmic reticlium

    • Biofluid Locations

    Not Available Tissue Location

  • Testes

    • Pathways

    Name SMPDB Link KEGG Link Alendronate pathwaySMP00095Not Available Atorvastatin PathwaySMP00131Not Available Cerivastatin PathwaySMP00111Not Available CHILD SyndromeSMP00387Not Available Cholesteryl ester storage diseaseSMP00508Not Available Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)SMP00388Not Available DesmosterolosisSMP00386Not Available Fluvastatin PathwaySMP00119Not Available Hyper-IgD syndromeSMP00509Not Available HypercholesterolemiaSMP00209Not Available Ibandronate PathwaySMP00079Not Available Lovastatin PathwaySMP00099Not Available Lysosomal Acid Lipase Deficiency (Wolman Disease)SMP00319Not Available Mevalonic aciduriaSMP00510Not Available Pamidronate PathwaySMP00117Not Available Pravastatin PathwaySMP00089Not Available Risedronate PathwaySMP00112Not Available Rosuvastatin PathwaySMP00092Not Available Simvastatin Action PathwaySMP00082Not Available Smith-Lemli-Opitz Syndrome (SLOS)SMP00389Not Available Steroid BiosynthesisSMP00023map00100 Wolman diseaseSMP00511Not Available Zoledronate PathwaySMP00107Not Available

    Normal Concentrations Not Available Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links 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 KEGG Compound ID

    C11455 BioCyc ID

    44-DIMETHYL-CHOLESTA-812-24-TRIENOL BiGG ID

    1454719 Wikipedia Link

    Not Available NuGOwiki Link

    HMDB01023 Metagene Link

    HMDB01023 METLIN ID

    5952 PubChem Compound

    443212 PDB ID

    Not Available ChEBI ID

    17813

    Product: ONO-4059 (hydrochloride)

    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 ]

    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 + NADPH details 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADP → 4,4-Dimethylcholesta-8,14,24-trienol + NADPH + Hydrogen Ion details
    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 + Water details

    PMID: 11911275

    By rofalproject

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