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24-methylidene-5alpha-cholest-8-en-3beta-ol (YMDB00545)

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. Thus, fecosterol is considered to be a sterol lipid molecule. fecosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
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-methionine → 24-methylidene-5alpha-cholest-8-en-3beta-ol + S-Adenosylhomocysteine + hydron
24-methylidene-5alpha-cholest-8-en-3beta-ol → episterol
KEGG Reactions
24-methylidene-5alpha-cholest-8-en-3beta-ol + oleoyl-CoA ↔ fecosteryl oleate + Coenzyme A
24-methylidene-5alpha-cholest-8-en-3beta-ol ↔ fecosteryl palmitoleate + Coenzyme A
24-methylidene-5alpha-cholest-8-en-3beta-ol → episterol
zymosterol + S-Adenosylmethionine → 24-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 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
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 IDNot Available
Pubchem Compound ID440371
Kegg IDC04525
ChemSpider ID22889876
FOODB IDFDB030856
Wikipedia IDFecosterol
BioCyc IDNot Available

Enzymes

Protein Details
1. Sterol O-acyltransferase 1
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.
Protein Details
2. Sterol 24-C-methyltransferase
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.
Protein Details
3. C-8 sterol isomerase
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
Protein Details
4. Sterol esterase TGL1
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.
Protein Details
5. Sterol esterase 1
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.
Protein Details
6. Sterol esterase 2
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

Protein Details
1. ATP-dependent permease AUS1
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
Protein Details
2. ATP-dependent permease PDR11
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