Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:06 UTC |
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HMDB ID | HMDB0000878 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ergosterol |
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Description | Ergosterol, also known as provitamin D2, 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 lipid molecule. Ergosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Ergosterol is the biological precursor to vitamin D2. It is turned into viosterol by ultraviolet light, and is then converted into ergocalciferol, which is a form of vitamin D. Ergosterol is a component of fungal cell membranes, serving the same function that cholesterol serves in animal cells. Ergosterol is not found in mammalian cell membranes. |
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Structure | [H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@H](C)C(C)C 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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Synonyms | Value | Source |
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(22E,24S)-24-Methylcholesta-5,7,22-trien-3beta-ol | ChEBI | Provitamin D2 | ChEBI | (22E,24S)-24-Methylcholesta-5,7,22-trien-3b-ol | Generator | (22E,24S)-24-Methylcholesta-5,7,22-trien-3β-ol | Generator | Lumisterol | HMDB | Provitamin D 2 | HMDB | D2, Pro-vitamin | HMDB | Pro vitamin D2 | HMDB | Pro-vitamin D2 | HMDB | (22E,24R)-Ergosta-5,7,22-trien-3beta-ol | HMDB | (22E,24R)-Ergosta-5,7,22-trien-3β-ol | HMDB | (24R)-Ergosta-5,7,22-trien-3beta-ol | HMDB | (24R)-Ergosta-5,7,22-trien-3β-ol | HMDB | (3beta,22E)-Ergosta-5,7,22-trien-3-ol | HMDB | (3Β,22E)-ergosta-5,7,22-trien-3-ol | HMDB | 24-Methylcholesta-5,7,22-trien-3beta-ol | HMDB | 24-Methylcholesta-5,7,22-trien-3β-ol | HMDB | 24R-Methylcholesta-5,7,22E-trien-3beta-ol | HMDB | 24R-Methylcholesta-5,7,22E-trien-3β-ol | HMDB | 24alpha-Methyl-22E-dehydrocholesterol | HMDB | 24Α-methyl-22E-dehydrocholesterol | HMDB | 3beta-Hydroxyergosta-5,7,22-triene | HMDB | 3Β-hydroxyergosta-5,7,22-triene | HMDB | Ergosterin | HMDB | Provitamin D | HMDB | Ergosterol | HMDB |
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Chemical Formula | C28H44O |
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Average Molecular Weight | 396.659 |
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Monoisotopic Molecular Weight | 396.339216037 |
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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 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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CAS Registry Number | 57-87-4 |
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SMILES | [H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@H](C)C(C)C |
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InChI Identifier | 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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InChI Key | DNVPQKQSNYMLRS-APGDWVJJSA-N |
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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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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Ergosterol GC-MS (1 TMS) | splash10-0536-2911000000-0f3a53ac2076470e08fd | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ergosterol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ergosterol GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ergosterol GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-06 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-07bg-6943000000-5fbc1f7b29d046df3944 | 2015-03-01 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Ergosterol 35V, Positive-QTOF | splash10-0fgo-0922000000-9e58e829d6b96c0c52ee | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ergosterol 10V, Positive-QTOF | splash10-004j-1019000000-9682b479cb367468e4f7 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ergosterol 20V, Positive-QTOF | splash10-01ss-6149000000-8fcdb7198ebd094e3658 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ergosterol 40V, Positive-QTOF | splash10-00li-9085000000-b5f06c3d8a32fea4fc08 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ergosterol 10V, Negative-QTOF | splash10-0002-0009000000-36b82459f90e5096bbff | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ergosterol 20V, Negative-QTOF | splash10-0002-0009000000-17e94d8c42f8b29d1d7a | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ergosterol 40V, Negative-QTOF | splash10-004i-3019000000-d968e794cb4f844efc59 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ergosterol 10V, Negative-QTOF | splash10-0002-0009000000-2f6aa9af0bd8878fb6c6 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ergosterol 20V, Negative-QTOF | splash10-0002-0009000000-5bdbce66488e82a677b2 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ergosterol 40V, Negative-QTOF | splash10-0006-0009000000-be11aef2535ad8ca3d13 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ergosterol 10V, Positive-QTOF | splash10-0002-0049000000-cc82bd885904a278a47b | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ergosterol 20V, Positive-QTOF | splash10-100r-8279000000-8081dfcf7f1cac20c1c1 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ergosterol 40V, Positive-QTOF | splash10-0apl-9330000000-662ba8b80c27a5fa1d58 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.009326 (0.003782-0.014870) uM | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB04038 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | C00023755 |
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Chemspider ID | 392539 |
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KEGG Compound ID | C01694 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Ergosterol |
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METLIN ID | Not Available |
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PubChem Compound | 444679 |
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PDB ID | Not Available |
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ChEBI ID | 16933 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1242781 |
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References |
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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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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. [PubMed:1287164 ]
- Liu TT, Lee RE, Barker KS, Lee RE, Wei L, Homayouni R, Rogers PD: Genome-wide expression profiling of the response to azole, polyene, echinocandin, and pyrimidine antifungal agents in Candida albicans. Antimicrob Agents Chemother. 2005 Jun;49(6):2226-36. [PubMed:15917516 ]
- Ferreira ME, Colombo AL, Paulsen I, Ren Q, Wortman J, Huang J, Goldman MH, Goldman GH: The ergosterol biosynthesis pathway, transporter genes, and azole resistance in Aspergillus fumigatus. Med Mycol. 2005 May;43 Suppl 1:S313-9. [PubMed:16110826 ]
- Akins RA: An update on antifungal targets and mechanisms of resistance in Candida albicans. Med Mycol. 2005 Jun;43(4):285-318. [PubMed:16110776 ]
- Matsumori N, Sawada Y, Murata M: Mycosamine orientation of amphotericin B controlling interaction with ergosterol: sterol-dependent activity of conformation-restricted derivatives with an amino-carbonyl bridge. J Am Chem Soc. 2005 Aug 3;127(30):10667-75. [PubMed:16045354 ]
- Kim DH, Jung SJ, Chung IS, Lee YH, Kim DK, Kim SH, Kwon BM, Jeong TS, Park MH, Seoung NS, Baek NI: Ergosterol peroxide from flowers of Erigeron annuus L. as an anti-atherosclerosis agent. Arch Pharm Res. 2005 May;28(5):541-5. [PubMed:15974439 ]
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