| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-05-29 13:27:36 -0600 |
| HMDB ID |
HMDB00554 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Dihydroandrosterone |
| Description |
Dihydroandrosterone is a major metabolite of testosterone. Dihydroandrosterone is the main steroid produced by the immature ovary; at puberty the synthesis of steroids shifts toward 4-ene-3-oxo steroids. testosterone 5a-reduced metabolites, including dihydrotestosterone are produced in the anterior pituitary and the central nervous system. Anabolic androgen steroid (AAS) are one of primary performance-enhancing substances abused by athletes. To defeat doping controls, athletes changed to take endogenous androgens from the application of synthetic AAS. testosterone was one candidate of endogenous androgens abused in sports. testosterone and its relevant steroids in urine is detected and monitored with GC/MS. The abuse of anabolic-androgenic steroids (AS) is a growing problem; however, the effects and mechanisms underlying their addictive effects are not well understood. (PMID: 17112575  , 6243214 , 491593 , 491592 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- Adiol
- Etiocholane-3a,17b-diol
- 3a,17b-Dihydroxy-5a-androstane
- 3a,5a-Tetrahydrotestosterone
- 3alpha,17beta-Dihydroxy-5alpha-androstane
- 5a-Androstane-3a,17b-diol
- 5alpha-Androstane-3alpha,17beta-androstanediol
- 5alpha-Androstane-3alpha,17beta-diol
- Androstane-3a,17b-diol
- Etiocholane-3alpha,17beta-diol
- Hombreol
|
| Chemical Formula |
C19H32O2 |
| Average Molecular Weight |
292.4562 |
| Monoisotopic Molecular Weight |
292.240230268 |
| IUPAC Name |
(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol |
| Traditional IUPAC Name |
5α-androstane-3α,17β-diol |
| CAS Registry Number |
1852-53-5 |
| SMILES |
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C |
| 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 |
| InChI Key |
CBMYJHIOYJEBSB-KHOSGYARSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Steroids and Steroid Derivatives |
| Sub Class |
Androgens and Derivatives |
| Other Descriptors |
- Aliphatic Homopolycyclic Compounds
- C19 steroids (androgens) and derivatives(Lipidmaps)
- Hydroxysteroids
- androstane-3alpha,17beta-diol(ChEBI)
|
| Substituents |
- Bicyclohexane
- Cyclic Alcohol
- Cyclohexane
- Decaline
- Secondary Alcohol
- Sesquiterpene Backbone
|
| Direct Parent |
Androgens and Derivatives |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Hormones, Membrane component
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
- Extracellular
- Membrane (predicted from logP)
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| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
219 - 221 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
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| Biological Properties |
|---|
| Cellular Locations |
- Extracellular
- Membrane (predicted from logP)
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| Biofluid Locations |
|
| Tissue Location |
|
| Pathways |
Not Available
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| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.000475 (0.000352-0.000548) uM |
Adult (>18 years old) |
Male |
Normal
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|
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022114 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
15039 |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB00554 |
| Metagene Link |
HMDB00554 |
| METLIN ID |
5538 |
| PubChem Compound |
15818 |
| PDB ID |
Not Available |
| ChEBI ID |
36713 |
| References |
|---|
| Synthesis Reference |
Kieslich, Klaus. 5a-Androstane-3a,17b-diol. Ger. Offen. (1980), 6 pp. |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- Deslypere JP, Vermeulen A: Aging and tissue androgens. J Clin Endocrinol Metab. 1981 Aug;53(2):430-4.
Pubmed: 7251820
- Rittmaster RS, Zwicker H, Thompson DL, Konok G, Norman RW: Androstanediol glucuronide production in human liver, prostate, and skin. Evidence for the importance of the liver in 5 alpha-reduced androgen metabolism. J Clin Endocrinol Metab. 1993 Apr;76(4):977-82.
Pubmed: 8473413
- Frye CA: Some rewarding effects of androgens may be mediated by actions of its 5alpha-reduced metabolite 3alpha-androstanediol. Pharmacol Biochem Behav. 2007 Feb;86(2):354-67. Epub 2006 Nov 15.
Pubmed: 17112575
- Eckstein B, Ravid R: Regulation of ovarian 17 beta-hydroxysteroid dehydrogenase activity by gonadotropin. Biochim Biophys Acta. 1980 Jan 17;627(2):165-71.
Pubmed: 6243214
- Celotti F, Farina JM, Santaniello E, Martini L, Motta M: Effect of testosterone, its 5 alpha-reduced metabolites and the corresponding propionates on testosterone metabolism--II. In the ventral prostate and in the seminal vesicles. J Steroid Biochem. 1979 Jul;11(1A):221-5.
Pubmed: 491593
- Celotti F, Farina JM, Santaniello E, Martini L, Motta M: Effect of testosterone, its 5 alpha-reduced metabolites and the corresponding propionates on testosterone metabolism. I--In the hypothalamus and in the anterior pituitary. J Steroid Biochem. 1979 Jul;11(1A):215-9.
Pubmed: 491592
|
