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Identification
YMDB IDYMDB00268
Name4,4-Dimethylcholesta-8,14,24-trienol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4,4-Dimethylcholesta-8,14,24-trienol, also known as FF-MAS or follicular fluid meiosis activating sterol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4,4-dimethylcholesta-8,14,24-trienol is considered to be a sterol lipid molecule. 4,4-Dimethylcholesta-8,14,24-trienol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • (3beta,5alpha)-4,4-dimethyl-Cholesta-8,14,24-trien-3-ol
  • (3beta,5alpha)-4,4-Dimethylcholesta-8,14,24-trien-3-ol
  • 4,4-Dimechol-8,14,24-trienol
  • 4,4-dimethyl-5-alpha-cholesta-8,14,24-trien-3-beta-ol
  • 4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3-ol
  • 4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol
  • 4,4-dimethyl-cholesta-8,14,24-trienol
  • 4,4-Dimethylcholesta-8,14,24-trienol
  • 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol
  • FF-MAS
  • follicular fluid meiosis activating sterol
  • 4,4-Dimethylcholesta-8(9),14,24-trien-3beta-ol
  • 4,4-Dimethylcholesta-8(9),14,24-trien-3b-ol
  • 4,4-Dimethylcholesta-8(9),14,24-trien-3β-ol
CAS number64284-64-6
WeightAverage: 410.6749
Monoisotopic: 410.354866094
InChI KeyLFQXEZVYNCBVDO-PBJLWWPKSA-N
InChIInChI=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
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
Chemical FormulaC29H46O
SMILES[H]O[C@@]1([H])C([H])([H])C([H])([H])[C@@]2(C3=C(C4=C([H])C([H])([H])[C@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])[C@@]4(C([H])([H])[H])C([H])([H])C3([H])[H])C([H])([H])C([H])([H])[C@@]2([H])C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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 Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity130.92 m³·mol⁻¹ChemAxon
Polarizability52.86 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Cholesterol biosynthesis and metabolism CE(10:0)PW002545 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(12:0)PW002548 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(14:0)PW002544 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(16:0)PW002550 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(18:0)PW002551 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Steroid biosynthesisec00100 Map00100
SMPDB Reactions
Lanosterin + oxygen + NADPH4,4-Dimethylcholesta-8,14,24-trienol + Formic acid + NADP + water
4,4-Dimethylcholesta-8,14,24-trienol + NADPH4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADP
KEGG Reactions
4,4-Dimethylcholesta-8,14,24-trienol + NADPH + hydronNADP + 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol
oxygen + NADH + hydron + Lanosterinwater + Formic acid + NAD + 4,4-Dimethylcholesta-8,14,24-trienol
oxygen + hydron + NADPH + LanosterinNADP + water + Formic acid + 4,4-Dimethylcholesta-8,14,24-trienol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-1009000000-416b93fbfcc925dc4766JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-4103900000-a8896cb66364cceda294JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0019500000-5b93d5ee5e25639470f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p6-2239100000-caf833ab905690ea16e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-4359000000-b7622993fbb821fcdd8aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-3773f1780255ea800890JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0005900000-43378c95eaacf13d3cd4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-1009000000-1387c3c0fba5a00f56a6JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Lamb, D. C., Kelly, D. E., Manning, N. J., Kaderbhai, M. A., Kelly, S. L. (1999). "Biodiversity of the P450 catalytic cycle: yeast cytochrome b5/NADH cytochrome b5 reductase complex efficiently drives the entire sterol 14-demethylation (CYP51) reaction." FEBS Lett 462:283-288.10622712
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 &
External Links:
ResourceLink
CHEBI ID17813
HMDB IDHMDB01023
Pubchem Compound ID443212
Kegg IDC11455
ChemSpider ID23232316
FOODB IDFDB022376
Wikipedia IDNot Available
BioCyc ID44-DIMETHYL-CHOLESTA-812-24-TRIENOL

Enzymes

General function:
Involved in iron ion binding
Specific function:
Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol
Gene Name:
ERG11
Uniprot ID:
P10614
Molecular weight:
60719.80078
Reactions
Obtusifoliol + 3 O(2) + 3 NADPH → 4-alpha-methyl-5-alpha-ergosta-8,14,24(28)-trien-3-beta-ol + formate + 3 NADP(+) + 4 H(2)O.
General function:
Involved in delta14-sterol reductase activity
Specific function:
Reduces the C14=C15 double bond of 4,4-dimethyl- cholesta-8,14,24-trienol to produce 4,4-dimethyl-cholesta-8,24- dienol
Gene Name:
ERG24
Uniprot ID:
P32462
Molecular weight:
50615.0
Reactions
4,4-dimethyl-5-alpha-cholesta-8,24-dien-3-beta-ol + NADP(+) → 4,4-dimethyl-5-alpha-cholesta-8,14,24-trien-3-beta-ol + NADPH.