| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:10:21 UTC |
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| Update date | 2019-11-26 03:07:35 UTC |
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| Primary ID | FDB012781 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | 7,8-Didehydrodesmosterol |
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| Description | Constituent of pig tissues and bakers yeast (Saccharomyces cerevisiae)
7-Dehydrodesmosterol is a sterol intermediate in the biosynthesis of steroids. 7-Dehydrodesmosterol is a substrate of the enzyme 24-dehydrocholesterol reductase (EC:1.3.1.72), an important enzyme in the biosynthesis of Cholesterol. Cholesterol is synthesized from either Lathosterol, 7-Dehydrocholesterol, Desmosterol or Cholestenol by the enzyme 3beta-hydroxysterol delta7 reductase (EC 1.3.1.21, Dhcr7). The Smith-Lemli-Opitz syndrome (SLOS, OMIM 270400) is caused by a genetic defect in cholesterol biosynthesis; mutations in the enzyme 3beta-hydroxysterol delta7 reductase lead to a failure of cholesterol synthesis, with an accumulation of precursor sterols, such as 7-Dehydrodesmosterol. SLOS results in craniofacial, limb as well as major organ defects, including the brain. In individuals with this syndrome, mental retardation, as well as other CNS dysfunction, is almost 100% prevalent. (PMID: 15862627, 17197219). 7,8-Didehydrodesmosterol is found in animal foods. |
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| CAS Number | 1715-86-2 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C27H42O |
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| IUPAC name | 2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol |
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| InChI Identifier | InChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9-10,19,21,23-25,28H,6,8,11-17H2,1-5H3 |
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| InChI Key | RUSSPKPUXDSHNC-UHFFFAOYSA-N |
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| Isomeric SMILES | CC(CCC=C(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C |
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| Average Molecular Weight | 382.6218 |
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| Monoisotopic Molecular Weight | 382.323565966 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. |
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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 | Cholestane steroids |
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| Direct Parent | Cholesterols and derivatives |
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| Alternative Parents | |
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| Substituents | - Cholesterol-skeleton
- Cholesterol
- 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 | |
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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 | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| EI-MS | Mass Spectrum (Electron Ionization) | Not Available | 2022-08-06 | View Spectrum | | Predicted GC-MS | 7,8-Didehydrodesmosterol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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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 | splash10-0159-0019000000-640d2c043114704aa68e | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0159-2159000000-f92f7b9f8ba169d0ff2b | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gb9-4459000000-86521888f6a07655c251 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0009000000-f27b309e4c0ec709176d | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0009000000-860c67ddd6590acc68d2 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014j-1019000000-9205d494e9dce5c57c99 | 2016-08-03 | View Spectrum |
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| NMR | |
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| External Links |
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| ChemSpider ID | 389458 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C05107 |
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| Pubchem Compound ID | 440558 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 27910 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB03896 |
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| CRC / DFC (Dictionary of Food Compounds) ID | HKX06-F:HKX07-G |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | 45126 |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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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 | Not Available |
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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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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | Not Available |
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| Pathways | |
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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 | |
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