Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:04:27 UTC |
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Update date | 2015-10-09 22:30:01 UTC |
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Primary ID | FDB021881 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Androsterone |
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Description | Androsterone is an inactive breakdown metabolite of testosterone, the product of a reaction mediated by the enzyme oxidative 17beta-hydroxysteroid dehydrogenase (EC 1.1.1.51, 17beta-HSD). Androsterone is also can be metabolized from other adrenal androgens such as dehydroepiandrosterone, dihydrotestosterone or androstenedione, and is considered an inactive end product; however, it can be a physiological effector in its own right. Androsterone might be converted back to dihydrotestosterone. Humans (and other primates) are unique among mammals in having high levels of circulating androsterone glucuronide, a process that is the major role uridine-diphospho-glucuronosyltransferase (EC 2.4.1.17, UGT) enzymes for glucuronidation of steroid metabolism in humans. Conjugation of androsterone is a pathway found in all vertebrates and is widely recognized that the liver is a major site of glucuronidation; however it is now clear that extrahepatic tissues are also involved in the conjugation of compounds to which these tissues are exposed. High levels of androsterone glucuronide found in the human prostate, breast cyst fluid and ovary follicular fluid suggest that glucuronidation of 5alpha-reduced C19 steroids occurs in these tissues as well. In doping control, the ratio of androsterone/etiocholanone provides valuable information that allows the assignment of a urine specimen to a particular person or the identification of urine samples with identical steroid profiles; this is particularly important to detect attempts of urine manipulation including urine alteration and substitution. (PMID: 9188497, 17017935, 14643063, 12943709, 9699884, 17260133) [HMDB] |
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CAS Number | 53-41-8 |
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Structure | |
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Synonyms | Synonym | Source |
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(3alpha,5alpha)-3-Hydroxy-androstan-17-one | HMDB | (3R,5S,8R,9S,10S,13S,14S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one | HMDB | 3-alpha-Hydroxy-17-androstanone | HMDB | 3-alpha-Hydroxy-5-alpha-androstan-17-one | HMDB | 3-alpha-Hydroxy-5-alpha-androstane-17-one | HMDB | 3-alpha-Hydroxy-5alpha-androstan-17-one | HMDB | 3-alpha-Hydroxyetioallocholan-17-one | HMDB | 3-Epihydroxyetioallocholan-17-one | HMDB | 3-Hydroxy-(3-alpha,5-alpha)-androstan-17-one | HMDB | 3-Hydroxyandrostan-17-one | HMDB | 3a-Hydroxyetioallocholan-17-one | HMDB | 3alpha-Hydroxy-17-androstanone | HMDB | 3alpha-Hydroxy-5alpha-androstan-17-one | HMDB | 3alpha-Hydroxyetioallocholan-17-one | HMDB | 5-alpha-Androstan-3-alpha-ol-17-one | HMDB | 5-alpha-Androstane-3alpha-ol-17-one | HMDB | 5-alpha-Androsterone | HMDB | 5a-Androstan-3a-ol-17-one | HMDB | 5a-Androstane-3a-ol-17-one | HMDB | 5a-Androsterone | HMDB | 5alpha-Androstane-3alpha-ol-17-one | HMDB | 5alpha-Androsterone | HMDB | Androkinine | HMDB | Androstanon-3-alpha-ol-17-one | HMDB | Androtine | HMDB | Atromide ici | HMDB | cis-Androsterone | HMDB | (3alpha,5alpha)-3-hydroxy-Androstan-17-one | hmdb | (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one | hmdb | 3-alpha-hydroxy-5alpha-Androstan-17-one | hmdb | 3-hydroxy-(3-alpha,5-alpha)-Androstan-17-one | hmdb | Androsterone | hmdb | Atromide ICI | hmdb |
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Predicted Properties | |
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Chemical Formula | C19H30O2 |
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IUPAC name | (1S,2S,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one |
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InChI Identifier | InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13?,14-,15-,16-,18-,19-/m0/s1 |
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InChI Key | QGXBDMJGAMFCBF-XYQQMQERSA-N |
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Isomeric SMILES | [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(O)CC[C@]12C |
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Average Molecular Weight | 290.4403 |
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Monoisotopic Molecular Weight | 290.224580204 |
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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
- Oxosteroid
- 17-oxosteroid
- Hydroxysteroid
- 3-hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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 | Not Available | |
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Melting Point | Not Available | |
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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 | Not Available | |
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Spectroscopic UV Data | Not Available | |
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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 | Type | Description | Splash Key | View |
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Predicted GC-MS | Androsterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03ea-0390000000-17f2f9f14aa5e282a19a | Spectrum | Predicted GC-MS | Androsterone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001i-2169000000-bf71d6f9c1a2a4af0d20 | 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, Negative | splash10-000i-0090000000-9e9f9de3b33af0311acd | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0090000000-fe9d47d83cd24c9d3a15 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0596-2190000000-513ad65531fff88b9f69 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dl-0190000000-c78d6bb7b08e2a97f5cc | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dl-0390000000-a2a8c979727ec005be63 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01rw-2890000000-de73b07d88fdae4d011a | 2015-09-15 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 23931264 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C00523 |
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Pubchem Compound ID | 12306765 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16032 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00031 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 35244 |
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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 | Androsterone |
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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 | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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UDP-glucuronosyltransferase 2B28 | UGT2B28 | Q9BY64 | UDP-glucuronosyltransferase 2B4 | UGT2B4 | P06133 | UDP-glucuronosyltransferase 1-4 | UGT1A4 | P22310 | UDP-glucuronosyltransferase 2B10 | UGT2B10 | P36537 | UDP-glucuronosyltransferase 2B7 | UGT2B7 | P16662 | UDP-glucuronosyltransferase 2B15 | UGT2B15 | P54855 | UDP-glucuronosyltransferase 2A1 | UGT2A1 | Q9Y4X1 | UDP-glucuronosyltransferase 1-1 | UGT1A1 | P22309 | UDP-glucuronosyltransferase 1-9 | UGT1A9 | O60656 | UDP-glucuronosyltransferase 1-8 | UGT1A8 | Q9HAW9 | UDP-glucuronosyltransferase 1-3 | UGT1A3 | P35503 | UDP-glucuronosyltransferase 1-10 | UGT1A10 | Q9HAW8 | UDP-glucuronosyltransferase 2B17 | UGT2B17 | O75795 | UDP-glucuronosyltransferase 1-6 | UGT1A6 | P19224 | UDP-glucuronosyltransferase 1-5 | UGT1A5 | P35504 | UDP-glucuronosyltransferase 2B11 | UGT2B11 | O75310 | UDP-glucuronosyltransferase 1-7 | UGT1A7 | Q9HAW7 | UDP-glucuronosyltransferase 2A3 | UGT2A3 | Q6UWM9 | Androgen receptor | AR | P10275 | Bile salt sulfotransferase | SULT2A1 | Q06520 | Dehydrogenase/reductase SDR family member 9 | DHRS9 | Q9BPW9 |
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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 | |
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