| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:07:47 -0700 |
| HMDB ID |
HMDB00031 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Androsterone |
| 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 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (3alpha,5alpha)-3-hydroxy-Androstan-17-one
- (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
- 3-alpha-Hydroxy-17-androstanone
- 3-alpha-Hydroxy-5-alpha-androstan-17-one
- 3-alpha-Hydroxy-5-alpha-androstane-17-one
- 3-alpha-Hydroxy-5alpha-Androstan-17-one
- 3-alpha-Hydroxyetioallocholan-17-one
- 3-Epihydroxyetioallocholan-17-one
- 3-Hydroxy-(3-alpha,5-alpha)-Androstan-17-one
- 3-Hydroxyandrostan-17-one
- 3a-Hydroxyetioallocholan-17-one
- 3alpha-Hydroxy-17-androstanone
- 3alpha-Hydroxy-5alpha-androstan-17-one
- 3alpha-Hydroxyetioallocholan-17-one
- 5-alpha-Androstan-3-alpha-ol-17-one
- 5-alpha-Androstane-3alpha-ol-17-one
- 5-alpha-Androsterone
- 5a-Androstan-3a-ol-17-one
- 5a-Androstane-3a-ol-17-one
- 5a-Androsterone
- 5alpha-Androstane-3alpha-ol-17-one
- 5alpha-Androsterone
- Androkinine
- Androstanon-3-alpha-ol-17-one
- Androsterone
- Androtine
- Atromide ICI
- cis-Androsterone
|
| Chemical Formula |
C19H30O2 |
| Average Molecular Weight |
290.4403 |
| Monoisotopic Molecular Weight |
290.224580204 |
| 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 |
| Traditional 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 |
| CAS Registry Number |
53-41-8 |
| SMILES |
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(O)CC[C@]12C |
| 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 |
| InChI Key |
QGXBDMJGAMFCBF-XYQQMQERSA-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
- Ketosteroids
|
| Substituents |
- Bicyclohexane
- Cyclic Alcohol
- Cyclohexane
- Decaline
- Ketone
- 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
|
| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
| Cellular locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
- Endoplasmic reticulum
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
185 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
0.012 mg/mL at 23 °C |
Not Available |
| LogP |
3.69 |
HANSCH,C ET AL. (1995) |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
- Endoplasmic reticulum
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Urine
|
| Tissue Location |
- Intestine
- Most Tissues
- Testes
- Primarily Liver
- Prostate
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.00065 (0.00053-0.00088) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.12 +/- 0.014 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.69-96.48 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.27 (0.23-0.33) umol/mmol creatinine |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.16 (0.11-0.18) umol/mmol creatinine |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.66 umol/mmol creatinine |
Children (1-13 year old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
6.69 +/- 1.65 umol/mmol creatinine |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.36 (0.11-0.67) umol/mmol creatinine |
Adult (>18 years old) |
Female |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
7.167e-05 +/- 0.000119 uM |
Adult (>18 years old) |
Not Specified |
Leuprolide acetate-induce hypogonadism |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.000142 +/- 9.475e-05 uM |
Adult (>18 years old) |
Not Specified |
Leuprolide acetate-induced hypogonadism with testosterone replacment |
Not Available |
| Urine |
Detected and Quantified |
|
0.000092 +/- 0.000082 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Stress urinary incontinence |
Not Available |
| Urine |
Detected and Quantified |
|
0.77 +/- 0.08 umol/mmol creatinine |
Adult (>18 years old) |
Female |
Hirsutism |
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 |
FDB021881 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
23931264 |
| KEGG Compound ID |
C00523 |
| BioCyc ID |
ANDROSTERONE |
| BiGG ID |
35244 |
| Wikipedia Link |
Androsterone |
| NuGOwiki Link |
HMDB00031 |
| Metagene Link |
HMDB00031 |
| METLIN ID |
2797 |
| PubChem Compound |
12306765 |
| PDB ID |
Not Available |
| ChEBI ID |
16032 |
| References |
|---|
| Synthesis Reference |
Marker, Russell E. Androsterone. Journal of the American Chemical Society (1935), 57 1755-6. |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- Muller L, Phillipou G: Quantification of 5 alpha- and 5 beta-androstanediols in urine by gas chromatography-mass spectrometry. Clin Chem. 1987 Feb;33(2 Pt 1):256-60.
Pubmed: 3802509
- Schonberger W, Benes P, Morsches B, Zabel B, Scheidt E: [Improvement in the longitudinal growth in Ullrich-Turner syndrome with oxandrolone. Function of urinary excretion of steroid hormones] Dtsch Med Wochenschr. 1982 Jul 2;107(26):1008-11.
Pubmed: 6211346
- Kim YS, Zhang H, Kim HY: Profiling neurosteroids in cerebrospinal fluids and plasma by gas chromatography/electron capture negative chemical ionization mass spectrometry. Anal Biochem. 2000 Jan 15;277(2):187-95.
Pubmed: 10625505
- Labows JN, Preti G, Hoelzle E, Leyden J, Kligman A: Steroid analysis of human apocrine secretion. Steroids. 1979 Sep;34(3):249-58.
Pubmed: 158859
- Raju U, Kadner S, Levitz M, Kaganowicz A, Blaustein A: Glucosiduronidation and esterification of androsterone by human breast tumors in vitro. Steroids. 1981 Apr;37(4):399-407.
Pubmed: 7245287
- Kaminski RM, Marini H, Kim WJ, Rogawski MA: Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia. 2005 Jun;46(6):819-27.
Pubmed: 15946323
- Grosse J, Anielski P, Hemmersbach P, Lund H, Mueller RK, Rautenberg C, Thieme D: Formation of 19-norsteroids by in situ demethylation of endogenous steroids in stored urine samples. Steroids. 2005 Jul;70(8):499-506. Epub 2005 Mar 29.
Pubmed: 15894033
- Toth I, Faredin I: Steroids excreted by human skin. II. C19-steroid sulphates in human axillary sweat. Acta Med Hung. 1985;42(1-2):21-8.
Pubmed: 3162156
- Teller WM, Homoki J, Wudy S, Schlickenrieder JH: Adrenarche is dissociated from gonadarche--studies in patients with Turner's syndrome. Acta Endocrinol Suppl (Copenh). 1986;279:232-40.
Pubmed: 2946134
- Mitamura K, Setaka M, Shimada K, Honma S, Namiki M, Koh E, Mizokami A: Determination of sulfates of androsterone and epiandrosterone in human serum using isotope diluted liquid chromatography-electrospray ionization-mass spectrometry. Biomed Chromatogr. 2005 Dec;19(10):796-801.
Pubmed: 15954157
- Tchedam Ngatcha B, Luu-The V, Labrie F, Poirier D: Androsterone 3alpha-ether-3beta-substituted and androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: chemical synthesis and structure-activity relationship. J Med Chem. 2005 Aug 11;48(16):5257-68.
Pubmed: 16078844
- Hammond GL: Endogenous steroid levels in the human prostate from birth to old age: a comparison of normal and diseased tissues. J Endocrinol. 1978 Jul;78(1):7-19.
Pubmed: 79632
|
| Enzymes |
|---|
|
|
| Name: |
Bile salt sulfotransferase
|
| Reactions: |
- (1) 3'-phosphoadenylyl sulfate + glycolithocholate = adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate [RN:R07287]
- (2) 3'-phosphoadenylyl sulfate + taurolithocholate = adenosine 3',5'-bisphosphate + taurolithocholate sulfate [RN:R03987]
|
| Gene Name: |
SULT2A1 |
| Uniprot ID: |
Q06520 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
