Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:23 UTC |
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Update date | 2019-11-26 03:07:41 UTC |
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Primary ID | FDB012828 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (3alpha,5alpha)-Androst-16-en-3-ol |
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Description | Aroma substance from the Perigord truffle tuber
Androstenol is a steroidal compound belonging to the group of odorous 16-androstenes, first isolated from boar testes and also found in humans. Androstenol has pheromone-like properties in both animals and humans, but the molecular targets of its pheromonal activity are unknown. Androstenol as a pheromone is well suited because of high volatility and lipophilicity. (PMID: 1419890, 8142319, 16415088); ; 3a-Hydroxyandrost-16-ene is a steroidal compound belonging to the group of odorous 16-androstenes, first isolated from boar testes and also found in humans. 3a-Hydroxyandrost-16-ene has pheromone-like properties in both animals and humans, but the molecular targets of its pheromonal activity are unknown. 3a-Hydroxyandrost-16-ene is structurally similar to endogenous A-ring reduced neurosteroids that act as positive modulators of GABAA receptors. 3a-Hydroxyandrost-16-ene has neurosteroid-like activity as a GABAA receptor modulator. The various actions of 3a-Hydroxyandrost-16-ene in the whole-animal models are consistent with its activity as a GABAA receptor modulator. GABAA receptors could represent a target for 3a-Hydroxyandrost-16-ene as a pheromone, for which it is well suited because of high volatility and lipophilicity, or as a conventional hormonal neurosteroid. (PMID: 1419890, 8142319, 16415088); Androstenol is an sex pheromone in pigs, possessing a musk-like odor.; The Pheromone Androstenol (5{alpha}-Androst-16-en-3{alpha}-ol) Is a Neurosteroid Positive Modulator of GABAA Receptors -- Kaminski RM, Marini H, Ortinski PI, Vicini S, Rogawski MA 317 (2): 694 -- Journal of Pharmacology and Experimental Therapeutics; The pheromone androstenol (5?-androst-16-en-3?-ol) is a neurosteroid positive modulator of GABAA receptors. |
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CAS Number | 1153-51-1 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C19H30O |
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IUPAC name | 2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol |
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InChI Identifier | InChI=1S/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3 |
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InChI Key | KRVXMNNRSSQZJP-UHFFFAOYSA-N |
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Isomeric SMILES | CC12CCC3C(CCC4CC(O)CCC34C)C1CC=C2 |
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Average Molecular Weight | 274.4409 |
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Monoisotopic Molecular Weight | 274.229665582 |
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Classification |
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Description | Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. |
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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 | Androstane steroids |
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Direct Parent | Androgens and derivatives |
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Alternative Parents | |
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Substituents | - Androgen-skeleton
- 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 | 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 | |
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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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Predicted GC-MS | (3alpha,5alpha)-Androst-16-en-3-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052b-0190000000-13328b1f40964b0accdc | Spectrum | Predicted GC-MS | (3alpha,5alpha)-Androst-16-en-3-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (3alpha,5alpha)-Androst-16-en-3-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (3alpha,5alpha)-Androst-16-en-3-ol, non-derivatized, 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 | splash10-0a6r-0090000000-1be7cd81baa4d84a3789 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a6r-1390000000-ed025605b018708efcde | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00mk-4590000000-855def90dad1c5c1e951 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0090000000-1541ebdd0dbc2495323f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0090000000-0ac5caa5bbe92d84a24d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-1190000000-cff2612a42b766eff16e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0090000000-8a564be2c0b3f79774ef | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-056r-1790000000-6a6baaf9b8c5d7717e45 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0535-9700000000-f613b5811b9167d439e4 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0090000000-c0274c5a0ec76c02edd6 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0090000000-c0274c5a0ec76c02edd6 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-0090000000-596a71488841027ba40b | 2021-10-12 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 92136 |
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ChEMBL ID | CHEMBL142348 |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 101989 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 40933 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB01889 |
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HMDB ID | HMDB05935 |
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CRC / DFC (Dictionary of Food Compounds) ID | HMB64-D:HMB65-E |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | ATE |
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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 | rw1010781 |
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SuperScent ID | Not Available |
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Wikipedia ID | Androstenol |
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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 | |
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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 | |
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Files |
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MSDS | show |
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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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