Record Information |
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Version | 4.0 |
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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 | 2017-12-07 01:17:12 UTC |
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HMDB ID | HMDB0000495 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Androstanediol |
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Description | Androstanediol is a metabolite of dihydrotestosterone, itself a metabolite of testosterone. Androstanediol is implicated in the regulation of gonadotropin secretion. As a metabolite of dihydroxytestosterone formed in the peripheral tissues, androstanediol and androstnediol-glucuronide can be used to estimate peripheral androgen activity. Androstanediol is a potential GABA (A) receptor-modulating neurosteroid with anticonvulsant properties and hence could act as a key neuromodulator in the central nervous system. It is considered that androstanediol has hedonic effects; therefore it is anticipated that androgens that are readily metabolized to androstanediol may have higher abuse potential than androgens that are not as easily metabolized to androstanediol. These results add to the growing literature indicating that athletes and non-athletes may be at considerable risk when they abuse androgens. (PMID: 11500254 , 16040068 , 11744084 ). |
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Structure | |
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Synonyms | Value | Source |
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Androstane-3,17-diol | Kegg | 3-a-Androstanediol | HMDB | 3-alpha-Androstanediol | HMDB | 3alpha-Androstanediol | HMDB | 5 a-Androstane-3 a, 17 b-diol | HMDB | 5 alpha-Androstane-3 alpha, 17 beta-diol | HMDB | 5-a-Androstane-3-a, 17-b-diol | HMDB | 5-alpha-Androstan-3-alpha,17-beta-diol | HMDB | 5-alpha-Androstane-3-a, 17-beta-diol | HMDB | 5-alpha-Androstane-3-alpha-17-beta-diol | HMDB | 5 Androstane 3,17 diol | MeSH | 5 alpha Androstane 3 alpha,17 beta diol | MeSH | 5 alpha Androstane 3 beta,17 alpha diol | MeSH | 5 alpha Androstane 3 beta,17 beta diol | MeSH | 5 alpha Androstane 3alpha,17 beta diol | MeSH | 5 alpha-Androstane-3 alpha,17 beta-diol | MeSH | 5 alpha-Androstane-3 beta,17 alpha-diol | MeSH | 5 alpha-Androstane-3 beta,17 beta-diol | MeSH | 5 alpha-Androstane-3alpha,17 beta-diol | MeSH | 5 beta Androstane 3 alpha,17 beta diol | MeSH | 5 beta-Androstane-3 alpha,17 beta-diol | MeSH | 5-Androstane-3,17-diol | MeSH | 5alpha Androstane 3beta,17alpha diol | MeSH | 5alpha-Androstane-3beta,17alpha-diol | MeSH | Androstane 3,17 diol | MeSH |
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Chemical Formula | C19H32O2 |
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Average Molecular Weight | 292.4562 |
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Monoisotopic Molecular Weight | 292.240230268 |
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IUPAC Name | (1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol |
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Traditional Name | (1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol |
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CAS Registry Number | 25126-76-5 |
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SMILES | [H][C@@]12CCC(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C |
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InChI Identifier | InChI=1S/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17?,18-,19-/m0/s1 |
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InChI Key | CBMYJHIOYJEBSB-UNPXRYTGSA-N |
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Chemical Taxonomy |
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Description | This compound 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
- 17-hydroxysteroid
- 3-alpha-hydroxysteroid
- 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 | - C19 steroids (androgens) and derivatives (C07632 )
- Androstane and derivatives (C07632 )
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | |
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General References | - Chetyrkin SV, Hu J, Gough WH, Dumaual N, Kedishvili NY: Further characterization of human microsomal 3alpha-hydroxysteroid dehydrogenase. Arch Biochem Biophys. 2001 Feb 1;386(1):1-10. [PubMed:11360992 ]
- Karlsson T, Vahlquist A, Kedishvili N, Torma H: 13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands? Biochem Biophys Res Commun. 2003 Mar 28;303(1):273-8. [PubMed:12646198 ]
- Thompson JA, Miles BS, Fennessey PV: Urinary organic acids quantitated by age groups in a healthy pediatric population. Clin Chem. 1977 Sep;23(9):1734-8. [PubMed:890917 ]
- Gupta MK, Guryev OL, Auchus RJ: 5alpha-reduced C21 steroids are substrates for human cytochrome P450c17. Arch Biochem Biophys. 2003 Oct 15;418(2):151-60. [PubMed:14522586 ]
- Secreto G, Toniolo P, Berrino F, Recchione C, Cavalleri A, Pisani P, Totis A, Fariselli G, Di Pietro S: Serum and urinary androgens and risk of breast cancer in postmenopausal women. Cancer Res. 1991 May 15;51(10):2572-6. [PubMed:2021938 ]
- Gratterola R: Anovulation and increased androgenic activity as breast cancer risk in women with fibrocystic disease of the breast. Cancer Res. 1978 Sep;38(9):3051-4. [PubMed:679211 ]
- Leszczynski DE, Schafer RM: Characterization of steroid hormone association with human plasma lipoproteins. Steroids. 1989 Jul;54(1):37-53. [PubMed:2815156 ]
- Thompson DL, Rittmaster RS, Rodriguez AM, Moore PH Jr, Rao PN: Synthesis of new steroid haptens for radioimmunoassay--VIII. Development and validation of a specific radioimmunoassay for serum 5 alpha-androstane-3 alpha, 17 beta-diol 17-glucuronide. J Steroid Biochem. 1990 Jul 4;36(4):345-9. [PubMed:2391963 ]
- Secreto G, Toniolo P, Berrino F, Recchione C, Di Pietro S, Fariselli G, Decarli A: Increased androgenic activity and breast cancer risk in premenopausal women. Cancer Res. 1984 Dec;44(12 Pt 1):5902-5. [PubMed:6498847 ]
- Ivell R, Balvers M, Anand RJ, Paust HJ, McKinnell C, Sharpe R: Differentiation-dependent expression of 17beta-hydroxysteroid dehydrogenase, type 10, in the rodent testis: effect of aging in Leydig cells. Endocrinology. 2003 Jul;144(7):3130-7. [PubMed:12810569 ]
- Wudy SA, Dorr HG, Solleder C, Djalali M, Homoki J: Profiling steroid hormones in amniotic fluid of midpregnancy by routine stable isotope dilution/gas chromatography-mass spectrometry: reference values and concentrations in fetuses at risk for 21-hydroxylase deficiency. J Clin Endocrinol Metab. 1999 Aug;84(8):2724-8. [PubMed:10443667 ]
- Keel BA, Abney TO: Oestrogenic regulation of testicular androgen production during development in the rat. J Endocrinol. 1985 May;105(2):211-8. [PubMed:2985727 ]
- Klemm W, Liebich HM, Gupta D: Plasma levels of 5alpha-androstane-3alpha,17beta-diol in boys during adolescent growth. J Clin Endocrinol Metab. 1976 Mar;42(3):514-9. [PubMed:1254692 ]
- Frye CA, Park D, Tanaka M, Rosellini R, Svare B: The testosterone metabolite and neurosteroid 3alpha-androstanediol may mediate the effects of testosterone on conditioned place preference. Psychoneuroendocrinology. 2001 Oct;26(7):731-50. [PubMed:11500254 ]
- Reddy DS, Venkatarangan L, Chien B, Ramu K: A high-performance liquid chromatography-tandem mass spectrometry assay of the androgenic neurosteroid 3alpha-androstanediol (5alpha-androstane-3alpha,17beta-diol) in plasma. Steroids. 2005 Dec 1;70(13):879-85. Epub 2005 Jul 22. [PubMed:16040068 ]
- Rosellini RA, Svare BB, Rhodes ME, Frye CA: The testosterone metabolite and neurosteroid 3alpha-androstanediol may mediate the effects of testosterone on conditioned place preference. Brain Res Brain Res Rev. 2001 Nov;37(1-3):162-71. [PubMed:11744084 ]
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