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| Identification |
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| YMDB ID | YMDB00545 |
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| Name | 24-methylidene-5alpha-cholest-8-en-3beta-ol |
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| Species | Saccharomyces cerevisiae |
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| Strain | Baker's yeast |
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| Description | fecosterol 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. |
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| Structure | |
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| 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
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| CAS number | 516-86-9 |
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| Weight | Average: 398.6642
Monoisotopic: 398.354866094 |
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| InChI Key | SLQKYSPHBZMASJ-QKPORZECSA-N |
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| InChI | InChI=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 |
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| 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 |
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| 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 |
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| Chemical Formula | C28H46O |
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| 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 |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Steroids and steroid derivatives |
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| Sub Class | Ergostane steroids |
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| Direct Parent | Ergosterols and derivatives |
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| Alternative Parents | |
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| Substituents | - Ergosterol-skeleton
- 3-beta-hydroxysteroid
- Hydroxysteroid
- 3-hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Not Available |
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| Charge | 0 |
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| Melting point | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Water Solubility | Not Available | PhysProp | | LogP | Not Available | PhysProp |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations | - extracellular
- cell envelope
- lipid particle
- endoplasmic reticulum
- cytoplasm
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| Organoleptic Properties | Not Available |
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| SMPDB Pathways | | Cholesterol biosynthesis and metabolism CE(10:0) | PW002545 |    | | Cholesterol biosynthesis and metabolism CE(12:0) | PW002548 |    | | Cholesterol biosynthesis and metabolism CE(14:0) | PW002544 |    | | Cholesterol biosynthesis and metabolism CE(16:0) | PW002550 |    | | Cholesterol biosynthesis and metabolism CE(18:0) | PW002551 |    |
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| KEGG Pathways | |
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| SMPDB Reactions | |
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| KEGG Reactions | |
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| Concentrations |
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| Intracellular Concentrations | Not Available |
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| Extracellular Concentrations | Not Available |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001j-0019000000-4a337e3ab572869d5978 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001j-6059000000-66cb566725fe3979de6f | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-6194000000-e66d0b9546e54d7c12b9 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0009000000-d618dab195514d0c7bd6 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0009000000-023dcac6f0c7eab01b94 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-2019000000-e6765e76cb50aa2e41b9 | JSpectraViewer |
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| References |
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| 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
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| Synthesis Reference: | Not Available |
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| External Links: | |
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