Identification
YMDB IDYMDB00545
Name24-methylidene-5alpha-cholest-8-en-3beta-ol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionfecosterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Based on a literature review very few articles have been published on fecosterol.
Structure
Thumb
Synonyms
  • 24-Methylene-5alpha-cholest-8-en-3beta-ol
  • Fecosterol
  • 24-Methylene-cholest-8-en-3beta-ol
  • delta-8(24),28-Ergostadienol
  • 24-Methylene-5a-cholest-8-en-3b-ol
  • 24-Methylene-5α-cholest-8-en-3β-ol
  • 24-Methylene-cholest-8-en-3b-ol
  • 24-Methylene-cholest-8-en-3β-ol
  • Δ-8(24),28-ergostadienol
  • (3beta)-Isomer OF fecosterol
CAS number516-86-9
WeightAverage: 398.6642
Monoisotopic: 398.354866094
InChI KeySLQKYSPHBZMASJ-QKPORZECSA-N
InChIInChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18,20-22,24-25,29H,3,7-17H2,1-2,4-6H3/t20-,21+,22+,24-,25+,27+,28-/m1/s1
IUPAC Name(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional IUPAC Name(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Chemical FormulaC28H46O
SMILES[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])CC3)[C@H](C)CCC(=C)C(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-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
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00083 g/LALOGPS
logP6.65ALOGPS
logP7.01ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)18.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.68 m³·mol⁻¹ChemAxon
Polarizability51.27 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cell envelope
  • lipid particle
  • endoplasmic reticulum
  • 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
zymosterol + S-Adenosyl-L-methionine24-methylidene-5alpha-cholest-8-en-3beta-ol + S-Adenosylhomocysteine + hydron
24-methylidene-5alpha-cholest-8-en-3beta-olepisterol
KEGG Reactions
24-methylidene-5alpha-cholest-8-en-3beta-ol + oleoyl-CoAfecosteryl oleate + Coenzyme A
24-methylidene-5alpha-cholest-8-en-3beta-olfecosteryl palmitoleate + Coenzyme A
24-methylidene-5alpha-cholest-8-en-3beta-olepisterol
zymosterol + S-Adenosylmethionine24-methylidene-5alpha-cholest-8-en-3beta-ol + S-Adenosylhomocysteine + hydron
24-methylidene-5alpha-cholest-8-en-3beta-ol + fatty acid ↔ fecosterol ester + water
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0019000000-4a337e3ab572869d5978JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-6059000000-66cb566725fe3979de6fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-6194000000-e66d0b9546e54d7c12b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-d618dab195514d0c7bd6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-023dcac6f0c7eab01b94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2019000000-e6765e76cb50aa2e41b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-0ca06bc1a59e9690d939JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-0ca06bc1a59e9690d939JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0019000000-c291f31f16695acf3118JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0039000000-64f7710a14da25c485d9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-8259000000-d9f24f47df06d778f58aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-9640000000-dc358966f446c6d8e5a7JSpectraViewer
MSMass Spectrum (Electron Ionization)Not AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • Wilcox, L. J., Balderes, D. A., Wharton, B., Tinkelenberg, A. H., Rao, G., Sturley, S. L. (2002). "Transcriptional profiling identifies two members of the ATP-binding cassette transporter superfamily required for sterol uptake in yeast." J Biol Chem 277:32466-32472.12077145
  • Schulz, T. A., Prinz, W. A. (2007). "Sterol transport in yeast and the oxysterol binding protein homologue (OSH) family." Biochim Biophys Acta 1771:769-780.17434796
  • Koffel, R., Tiwari, R., Falquet, L., Schneiter, R. (2005). "The Saccharomyces cerevisiae YLL012/YEH1, YLR020/YEH2, and TGL1 genes encode a novel family of membrane-anchored lipases that are required for steryl ester hydrolysis." Mol Cell Biol 25:1655-1668.15713625
  • Zweytick, D., Leitner, E., Kohlwein, S. D., Yu, C., Rothblatt, J., Daum, G. (2000). "Contribution of Are1p and Are2p to steryl ester synthesis in the yeast Saccharomyces cerevisiae." Eur J Biochem 267:1075-1082.10672016
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17038
HMDB IDHMDB0304351
Pubchem Compound ID440371
Kegg IDC04525
ChemSpider ID22889876
FOODB IDFDB030856
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in O-acyltransferase activity
Specific function:
Acyl-CoA + cholesterol = CoA + cholesterol ester
Gene Name:
ARE1
Uniprot ID:
P25628
Molecular weight:
71612.5
Reactions
Acyl-CoA + cholesterol → CoA + cholesterol ester.
General function:
Involved in methyltransferase activity
Specific function:
Catalyzes the methyl transfer from S-adenosyl-methionine to the C-24 of zymosterol to form fecosterol
Gene Name:
ERG6
Uniprot ID:
P25087
Molecular weight:
43430.5
Reactions
S-adenosyl-L-methionine + 5-alpha-cholesta-8,24-dien-3-beta-ol → S-adenosyl-L-homocysteine + 24-methylene-5-alpha-cholest-8-en-3-beta-ol.
General function:
Involved in C-8 sterol isomerase activity
Specific function:
Catalyzes the reaction which results in unsaturation at C-7 in the B ring of sterols
Gene Name:
ERG2
Uniprot ID:
P32352
Molecular weight:
24895.40039
Reactions
General function:
Involved in lipid metabolic process
Specific function:
Mediates the hydrolysis of steryl esters. Required for mobilization of steryl ester, thereby playing a central role in lipid metabolism. May have weak lipase activity toward triglycerides upon some conditions, however, the relevance of such activity is unclear in vivo
Gene Name:
TGL1
Uniprot ID:
P34163
Molecular weight:
62978.39844
Reactions
A steryl ester + H(2)O → a sterol + a fatty acid.
General function:
Involved in lipid metabolic process
Specific function:
Mediates the hydrolysis of steryl esters, thereby playing a central role in lipid metabolism. Under heme-deficient conditions, it constitutes the major steryl ester hydrolase, suggesting that it plays a central role in mobilization of steryl esters under anaerobic conditions
Gene Name:
YEH1
Uniprot ID:
Q07804
Molecular weight:
66507.39844
Reactions
A steryl ester + H(2)O → a sterol + a fatty acid.
General function:
Involved in lipid metabolic process
Specific function:
Mediates the hydrolysis of steryl esters. Required for mobilization of steryl ester, thereby playing a central role in lipid metabolism
Gene Name:
YEH2
Uniprot ID:
Q07950
Molecular weight:
62446.0
Reactions
A steryl ester + H(2)O → a sterol + a fatty acid.

Transporters

General function:
Involved in ATP binding
Specific function:
Transporter involved in the uptake of sterol
Gene Name:
AUS1
Uniprot ID:
Q08409
Molecular weight:
157750.0
General function:
Involved in ATP binding
Specific function:
Transporter involved in the uptake of sterol
Gene Name:
PDR11
Uniprot ID:
P40550
Molecular weight:
160536.0