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| Identification |
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| YMDB ID | YMDB00543 |
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| Name | ergosterol |
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| Species | Saccharomyces cerevisiae |
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| Strain | Baker's yeast |
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| Description | Ergosterol, also known as provitamin D2 or lumisterol, 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, ergosterol is considered to be a sterol. Based on a literature review a significant number of articles have been published on Ergosterol. |
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| Structure | |
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| Synonyms | - (22E)-Ergosta-5,7,22-trien-3-ol
- (24R)-Ergosta-5,7,22-trien-3b-ol
- (3beta,22E)-Ergosta-5,7,22-trien-3-ol
- (3beta,2E)-Ergosta-5,7,22-trien-3-ol
- (3beta)-Ergosta-5,7,22-trien-3-ol
- 24-Methylcholesta-5,7,22-trien-3b-ol
- 24-Methylcholesta-5,7,22-trien-3beta-ol
- 24a-Methyl-22E-dehydrocholesterol
- 24alpha-Methyl-22E-dehydrocholestero
- 24R-Methylcholesta-5,7,22E-trien-3b-ol
- 24R-Methylcholesta-5,7,22E-trien-3beta-ol
- ergosta-5,7,22-trien-3-ol
- Ergosterin
- Ergosterol
- Provitamine D2
- (22E,24S)-24-Methylcholesta-5,7,22-trien-3beta-ol
- Provitamin D2
- (22E,24S)-24-Methylcholesta-5,7,22-trien-3b-ol
- (22E,24S)-24-Methylcholesta-5,7,22-trien-3β-ol
- Lumisterol
- Provitamin D 2
- D2, Pro-vitamin
- Pro vitamin D2
- Pro-vitamin D2
- (22E,24R)-Ergosta-5,7,22-trien-3beta-ol
- (22E,24R)-Ergosta-5,7,22-trien-3β-ol
- (24R)-Ergosta-5,7,22-trien-3beta-ol
- (24R)-Ergosta-5,7,22-trien-3β-ol
- (3Β,22E)-ergosta-5,7,22-trien-3-ol
- 24-Methylcholesta-5,7,22-trien-3β-ol
- 24R-Methylcholesta-5,7,22E-trien-3β-ol
- 24alpha-Methyl-22E-dehydrocholesterol
- 24Α-methyl-22E-dehydrocholesterol
- 3beta-Hydroxyergosta-5,7,22-triene
- 3Β-hydroxyergosta-5,7,22-triene
- Provitamin D
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| CAS number | 57-87-4 |
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| Weight | Average: 396.6484
Monoisotopic: 396.33921603 |
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| InChI Key | DNVPQKQSNYMLRS-APGDWVJJSA-N |
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| InChI | InChI=1S/C28H44O/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/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1 |
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| IUPAC Name | (1S,2R,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol |
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| Traditional IUPAC Name | (1S,2R,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol |
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| Chemical Formula | C28H44O |
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| SMILES | CC(C)[C@@H](C)\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C |
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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-hydroxy-delta-5-steroid
- 3-hydroxy-delta-7-steroid
- 3-hydroxysteroid
- Hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- 3-beta-hydroxysteroid
- Delta-7-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Alcohol
- Organooxygen compound
- Hydrocarbon derivative
- 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 | Solid |
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| Charge | 0 |
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| Melting point | 170 °C |
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| Experimental Properties | | Property | Value | Reference |
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| Water Solubility | 16 mg/mL [HMP experimental] | 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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| GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-0536-2911000000-0f3a53ac2076470e08fd | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0fgo-0922000000-9e58e829d6b96c0c52ee | JSpectraViewer | MoNA | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004j-1019000000-9682b479cb367468e4f7 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01ss-6149000000-8fcdb7198ebd094e3658 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00li-9085000000-b5f06c3d8a32fea4fc08 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0009000000-36b82459f90e5096bbff | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0009000000-17e94d8c42f8b29d1d7a | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-3019000000-d968e794cb4f844efc59 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0009000000-2f6aa9af0bd8878fb6c6 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0009000000-5bdbce66488e82a677b2 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-0009000000-be11aef2535ad8ca3d13 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0049000000-cc82bd885904a278a47b | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-100r-8279000000-8081dfcf7f1cac20c1c1 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0apl-9330000000-662ba8b80c27a5fa1d58 | JSpectraViewer | | MS | Mass Spectrum (Electron Ionization) | splash10-07bg-6943000000-5fbc1f7b29d046df3944 | JSpectraViewer | MoNA | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | 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
- 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
- Loubbardi, A., Marcireau, C., Karst, F., Guilloton, M. (1995). "Sterol uptake induced by an impairment of pyridoxal phosphate synthesis in Saccharomyces cerevisiae: cloning and sequencing of the PDX3 gene encoding pyridoxine (pyridoxamine) phosphate oxidase." J Bacteriol 177:1817-1823.7896706
- 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
- Warnecke, D., Erdmann, R., Fahl, A., Hube, B., Muller, F., Zank, T., Zahringer, U., Heinz, E. (1999). "Cloning and functional expression of UGT genes encoding sterol glucosyltransferases from Saccharomyces cerevisiae, Candida albicans, Pichia pastoris, and Dictyostelium discoideum." J Biol Chem 274:13048-13059.10224056
- 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: | He, Xiuping; Zhang, Borun; Tan, Huarong. Overexpression of a sterol C-24(28) reductase increases ergosterol production in Saccharomyces cerevisiae. Biotechnology Letters (2003), 25(10), 773-778. |
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| External Links: | |
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