Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:16 UTC |
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Update date | 2019-11-26 03:07:12 UTC |
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Primary ID | FDB012612 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Ergosterol |
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Description | Ergosterol 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. Ergosterol is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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CAS Number | 57-87-4 |
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Structure | |
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Synonyms | Synonym | Source |
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(22E)-Ergosta-5,7,22-trien-3-ol | biospider | (22E)-Ergosta-5,7,22-trien-3beta-ol | biospider | (24R)-Ergosta-5,7,22-trien-3b-ol | biospider | (3β,22E)-Ergosta-5,7,22-trien-3-ol | biospider | (3β)-Ergosta-5,7,22- trien-3-ol | biospider | (3beta,22E)-Ergosta-5,7,22-trien-3-ol | biospider | (3beta,2e)-Ergosta-5,7,22-trien-3-ol | HMDB | (3beta)-Ergosta-5,7,22-trien-3-ol | biospider | 24-Methylcholesta-5,7,22-trien-3b-ol | biospider | 24-Methylcholesta-5,7,22-trien-3beta-ol | biospider | 24a-Methyl-22E-dehydrocholesterol | biospider | 24alpha-Methyl-22E-dehydrocholestero | biospider | 24R-Methylcholesta-5,7,22E-trien-3b-ol | biospider | 24R-Methylcholesta-5,7,22E-trien-3beta-ol | biospider | 3beta-Hydroxy-5,7,22-ergostatriene | biospider | 5,7,22-Ergostatrien-3beta-ol | biospider | Ergosta-5,7,22-trien-3-ol | biospider | Ergosterin | db_source | Ergosterol | db_source | Ertron | db_source | Provitamin D2 | db_source | Provitamine D2 | biospider |
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Predicted Properties | |
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Chemical Formula | C28H44O |
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IUPAC name | 14-[(3E)-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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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+ |
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InChI Key | DNVPQKQSNYMLRS-BQYQJAHWSA-N |
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Isomeric SMILES | CC(C)C(C)\C=C\C(C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C |
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Average Molecular Weight | 396.6484 |
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Monoisotopic Molecular Weight | 396.33921603 |
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Classification |
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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
- Hydroxysteroid
- 3-hydroxysteroid
- 3-hydroxy-delta-7-steroid
- 3-hydroxy-delta-5-steroid
- Delta-7-steroid
- Delta-5-steroid
- 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 | Not Available |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 84.79%; H 11.18%; O 4.03% | DFC |
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Melting Point | Mp 168° (165°) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]D -133 (CHCl3) | DFC |
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Spectroscopic UV Data | 293 () (EtOH) (Berdy) | DFC |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Not Available |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004j-1019000000-9682b479cb367468e4f7 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01ss-6149000000-8fcdb7198ebd094e3658 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00li-9085000000-b5f06c3d8a32fea4fc08 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0009000000-36b82459f90e5096bbff | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0009000000-17e94d8c42f8b29d1d7a | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-3019000000-d968e794cb4f844efc59 | 2016-08-03 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 10477914 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C01694 |
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Pubchem Compound ID | 21775588 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16933 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB04038 |
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HMDB ID | HMDB00878 |
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CRC / DFC (Dictionary of Food Compounds) ID | NXR27-J:HJJ37-Q |
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EAFUS ID | Not Available |
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Dr. Duke ID | ERGOSTEROL|7-ERGOSTEROL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00003652 |
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HET ID | 1BXM |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Ergosterol |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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Anti-angiogenic | 48422 | An agent that inhibits the formation of new blood vessels, playing a crucial role in cancer treatment by starving tumors of oxygen and nutrients. Therapeutically, it is used to manage cancer, age-related macular degeneration, and other diseases characterized by excessive angiogenesis, reducing tumor growth and slowing disease progression. | DUKE | Anti-flu | 22587 | An agent that prevents or treats influenza virus infections, reducing symptoms and complications. Its biological role involves blocking viral replication, and its therapeutic applications include prophylaxis and treatment of flu outbreaks. Key medical uses include reducing the risk of flu-related hospitalizations and mortality, especially in high-risk populations such as the elderly and young children. | DUKE | Antitumor | 35610 | An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes. | DUKE | Anti-viral | 22587 | An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19. | DUKE | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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