Human Metabolome Database Version 3.5

Showing metabocard for Androsterone (HMDB00031)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:24:31 -0600
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 Link_out, 17017935 Link_out, 14643063 Link_out, 12943709 Link_out, 9699884 Link_out, 17260133 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 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
  • 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
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
Property Value Source
Water Solubility 0.0063 g/L ALOGPS
LogP 3.71 ALOGPS
LogP 3.77 ChemAxon
LogS -4.66 ALOGPS
pKa (strongest acidic) 18.3 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 83.81 ChemAxon
Polarizability 34.7 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
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
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.00065 (0.00053-0.00088) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.12 +/- 0.014 uM Adult (>18 years old) Male Normal
Urine Detected and Quantified
0.69-96.48 umol/mmol creatinine Adult (>18 years old) Both Normal
  • David F. Put...
Urine Detected and Quantified
0.27 (0.23-0.33) umol/mmol creatinine Adult (>18 years old) Male Normal
Urine Detected and Quantified
0.16 (0.11-0.18) umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected and Quantified
0.66 umol/mmol creatinine Children (1-13 year old) Both Normal
Urine Detected and Quantified
6.69 +/- 1.65 umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected and Quantified
0.36 (0.11-0.67) umol/mmol creatinine Adult (>18 years old) Female Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 7.167e-05 +/- 0.000119 uM Adult (>18 years old) Not Specified Leuprolide acetate-induce hypogonadism
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
Urine Detected and Quantified 0.000092 +/- 0.000082 umol/mmol creatinine Adult (>18 years old) Both Stress urinary incontinence
Urine Detected and Quantified 0.77 +/- 0.08 umol/mmol creatinine Adult (>18 years old) Female Hirsutism
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite 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 Link_out
KEGG Compound ID C00523 Link_out
BioCyc ID ANDROSTERONE Link_out
BiGG ID 35244 Link_out
Wikipedia Link Androsterone Link_out
NuGOwiki Link HMDB00031 Link_out
Metagene Link HMDB00031 Link_out
METLIN ID 2797 Link_out
PubChem Compound 12306765 Link_out
PDB ID Not Available
ChEBI ID 16032 Link_out
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
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. Kaminski RM, Marini H, Kim WJ, Rogawski MA: Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia. 2005 Jun;46(6):819-27. Pubmed: 15946323 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. 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 Link_out
  12. 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 Link_out
  13. 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 Link_out
  14. 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 Link_out
  15. 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 Link_out
  16. 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 Link_out
  17. 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 Link_out
  18. 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 Link_out

Enzymes
Name: Aldo-keto reductase family 1 member C4
Reactions:
Androsterone + NAD unknown Androstanedione + NADH + Hydrogen Ion details
Androsterone + NADP unknown Androstanedione + NADPH + Hydrogen Ion details
Gene Name: AKR1C4
Uniprot ID: P17516 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile salt sulfotransferase
Reactions: Not Available
Gene Name: SULT2A1
Uniprot ID: Q06520 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldo-keto reductase family 1 member C3
Reactions: Not Available
Gene Name: AKR1C3
Uniprot ID: P42330 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldo-keto reductase family 1 member C1
Reactions: Not Available
Gene Name: AKR1C1
Uniprot ID: Q04828 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldo-keto reductase family 1 member C2
Reactions: Not Available
Gene Name: AKR1C2
Uniprot ID: P52895 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B28
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT2B28
Uniprot ID: Q9BY64 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B4
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT2B4
Uniprot ID: P06133 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-4
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT1A4
Uniprot ID: P22310 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B10
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT2B10
Uniprot ID: P36537 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B7
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT2B7
Uniprot ID: P16662 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B15
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT2B15
Uniprot ID: P54855 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2A1
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT2A1
Uniprot ID: Q9Y4X1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-1
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT1A1
Uniprot ID: P22309 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-9
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT1A9
Uniprot ID: O60656 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-8
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT1A8
Uniprot ID: Q9HAW9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-3
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT1A3
Uniprot ID: P35503 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-10
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT1A10
Uniprot ID: Q9HAW8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B17
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT2B17
Uniprot ID: O75795 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-6
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT1A6
Uniprot ID: P19224 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-5
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT1A5
Uniprot ID: P35504 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B11
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT2B11
Uniprot ID: O75310 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-7
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT1A7
Uniprot ID: Q9HAW7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Androgen receptor
Reactions: Not Available
Gene Name: AR
Uniprot ID: P10275 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dehydrogenase/reductase SDR family member 9
Reactions: Not Available
Gene Name: DHRS9
Uniprot ID: Q9BPW9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Retinol dehydrogenase 16
Reactions: Not Available
Gene Name: RDH16
Uniprot ID: O75452 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2A3
Reactions:
Androsterone + Uridine diphosphate glucuronic acid unknown Androsterone glucuronide + Uridine 5'-diphosphate details
Gene Name: UGT2A3
Uniprot ID: Q6UWM9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: HCG2039726, isoform CRA_f
Reactions: Not Available
Gene Name: UGT1A10
Uniprot ID: Q5DT02 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: HCG2039726, isoform CRA_e
Reactions: Not Available
Gene Name: UGT1A8
Uniprot ID: Q5DSZ6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP glycosyltransferase 1 family polypeptide A7
Reactions: Not Available
Gene Name: UGT1A7
Uniprot ID: Q5DSZ7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA