Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:24:31 UTC
HMDB IDHMDB00031
Secondary Accession NumbersNone
Metabolite Identification
Common NameAndrosterone
DescriptionAndrosterone 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
Thumb
Synonyms
  1. (3alpha,5alpha)-3-hydroxy-Androstan-17-one
  2. (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. 3-alpha-Hydroxy-17-androstanone
  4. 3-alpha-Hydroxy-5-alpha-androstan-17-one
  5. 3-alpha-Hydroxy-5-alpha-androstane-17-one
  6. 3-alpha-Hydroxy-5alpha-Androstan-17-one
  7. 3-alpha-Hydroxyetioallocholan-17-one
  8. 3-Epihydroxyetioallocholan-17-one
  9. 3-Hydroxy-(3-alpha,5-alpha)-Androstan-17-one
  10. 3-Hydroxyandrostan-17-one
  11. 3a-Hydroxyetioallocholan-17-one
  12. 3alpha-Hydroxy-17-androstanone
  13. 3alpha-Hydroxy-5alpha-androstan-17-one
  14. 3alpha-Hydroxyetioallocholan-17-one
  15. 5-alpha-Androstan-3-alpha-ol-17-one
  16. 5-alpha-Androstane-3alpha-ol-17-one
  17. 5-alpha-Androsterone
  18. 5a-Androstan-3a-ol-17-one
  19. 5a-Androstane-3a-ol-17-one
  20. 5a-Androsterone
  21. 5alpha-Androstane-3alpha-ol-17-one
  22. 5alpha-Androsterone
  23. Androkinine
  24. Androstanon-3-alpha-ol-17-one
  25. Androsterone
  26. Androtine
  27. Atromide ICI
  28. cis-Androsterone
Chemical FormulaC19H30O2
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
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 Number53-41-8
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 KeyQGXBDMJGAMFCBF-XYQQMQERSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassAndrogens 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 ParentAndrogens and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point185 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 mg/mL at 23 °CNot Available
LogP3.69HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility0.0063 g/LALOGPS
logP3.71ALOGPS
logP3.77ChemAxon
logS-4.7ALOGPS
pKa (strongest acidic)18.3ChemAxon
pKa (strongest basic)-1.4ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area37.3ChemAxon
rotatable bond count0ChemAxon
refractivity83.81ChemAxon
polarizability34.7ChemAxon
Spectra
SpectraNot 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
  • Primarily Liver
  • Prostate
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.00065 (0.00053-0.00088) uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.12 +/- 0.014 uMAdult (>18 years old)MaleNormal
UrineDetected and Quantified0.69-96.48 umol/mmol creatinineAdult (>18 years old)BothNormal
  • David F. Put...
UrineDetected and Quantified0.27 (0.23-0.33) umol/mmol creatinineAdult (>18 years old)MaleNormal
UrineDetected and Quantified0.16 (0.11-0.18) umol/mmol creatinineAdult (>18 years old)FemaleNormal
UrineDetected and Quantified0.66 umol/mmol creatinineChildren (1-13 year old)BothNormal
UrineDetected and Quantified6.69 +/- 1.65 umol/mmol creatinineAdult (>18 years old)FemaleNormal
UrineDetected and Quantified0.36 (0.11-0.67) umol/mmol creatinineAdult (>18 years old)FemaleNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cerebrospinal Fluid (CSF)Detected and Quantified7.167e-05 +/- 0.000119 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induce hypogonadism
Cerebrospinal Fluid (CSF)Detected and Quantified0.000142 +/- 9.475e-05 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism with testosterone replacment
UrineDetected and Quantified0.000092 +/- 0.000082 umol/mmol creatinineAdult (>18 years old)BothStress urinary incontinence
UrineDetected and Quantified0.77 +/- 0.08 umol/mmol creatinineAdult (>18 years old)FemaleHirsutism
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021881
KNApSAcK IDNot Available
Chemspider ID23931264
KEGG Compound IDC00523
BioCyc IDANDROSTERONE
BiGG ID35244
Wikipedia LinkAndrosterone
NuGOwiki LinkHMDB00031
Metagene LinkHMDB00031
METLIN ID2797
PubChem Compound12306765
PDB IDNot Available
ChEBI ID16032
References
Synthesis ReferenceMarker, Russell E. Androsterone. Journal of the American Chemical Society (1935), 57 1755-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Biswas MG, Russell DW: Expression cloning and characterization of oxidative 17beta- and 3alpha-hydroxysteroid dehydrogenases from rat and human prostate. J Biol Chem. 1997 Jun 20;272(25):15959-66. Pubmed: 9188497
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. Kaminski RM, Marini H, Kim WJ, Rogawski MA: Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia. 2005 Jun;46(6):819-27. Pubmed: 15946323
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. Thevis M, Geyer H, Mareck U, Sigmund G, Henke J, Henke L, Schanzer W: Detection of manipulation in doping control urine sample collection: a multidisciplinary approach to determine identical urine samples. Anal Bioanal Chem. 2007 Aug;388(7):1539-43. Epub 2007 Jan 27. Pubmed: 17260133
  15. Matsuzaki Y, Honda A: Dehydroepiandrosterone and its derivatives: potentially novel anti-proliferative and chemopreventive agents. Curr Pharm Des. 2006;12(26):3411-21. Pubmed: 17017935
  16. Belanger A, Pelletier G, Labrie F, Barbier O, Chouinard S: Inactivation of androgens by UDP-glucuronosyltransferase enzymes in humans. Trends Endocrinol Metab. 2003 Dec;14(10):473-9. Pubmed: 14643063
  17. Barbier O, Belanger A: The cynomolgus monkey (Macaca fascicularis) is the best animal model for the study of steroid glucuronidation. J Steroid Biochem Mol Biol. 2003 Jun;85(2-5):235-45. Pubmed: 12943709
  18. Belanger A, Hum DW, Beaulieu M, Levesque E, Guillemette C, Tchernof A, Belanger G, Turgeon D, Dubois S: Characterization and regulation of UDP-glucuronosyltransferases in steroid target tissues. J Steroid Biochem Mol Biol. 1998 Apr;65(1-6):301-10. Pubmed: 9699884

Enzymes

Gene Name:
AKR1C4
Uniprot ID:
P17516
Reactions
Androsterone + NAD unknown Androstanedione + NADH + Hydrogen Iondetails
Androsterone + NADP unknown Androstanedione + NADPH + Hydrogen Iondetails
Gene Name:
SULT2A1
Uniprot ID:
Q06520
Gene Name:
AKR1C3
Uniprot ID:
P42330
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Gene Name:
AKR1C2
Uniprot ID:
P52895
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2B4
Uniprot ID:
P06133
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A4
Uniprot ID:
P22310
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2B10
Uniprot ID:
P36537
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2B7
Uniprot ID:
P16662
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2B15
Uniprot ID:
P54855
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A1
Uniprot ID:
P22309
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A9
Uniprot ID:
O60656
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A3
Uniprot ID:
P35503
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A10
Uniprot ID:
Q9HAW8
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2B17
Uniprot ID:
O75795
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A6
Uniprot ID:
P19224
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A5
Uniprot ID:
P35504
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2B11
Uniprot ID:
O75310
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A7
Uniprot ID:
Q9HAW7
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
AR
Uniprot ID:
P10275
Gene Name:
RDH16
Uniprot ID:
O75452
Gene Name:
UGT2A3
Uniprot ID:
Q6UWM9
Reactions
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A10
Uniprot ID:
Q5DT02
Gene Name:
UGT1A8
Uniprot ID:
Q5DSZ6