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Bovine Metabolome Database



Showing metabocard for Androsterone (BMDB00031)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-08-05 12:54:07
Accession Number BMDB00031
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)
Synonyms
  1. (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
  2. (3alpha,5alpha)-3-hydroxy-Androstan-17-one
  3. 3-Epihydroxyetioallocholan-17-one
  4. 3-Hydroxyandrostan-17-one
  5. 3-alpha-Hydroxy-17-androstanone
  6. 3-alpha-Hydroxy-5-alpha-androstan-17-one
  7. 3-alpha-Hydroxy-5-alpha-androstane-17-one
  8. 3-alpha-Hydroxyetioallocholan-17-one
  9. 3-alpha-hydroxy-5alpha-Androstan-17-one
  10. 3-hydroxy-(3-alpha,5-alpha)-Androstan-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 IUPAC Name (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
Chemical Formula C19H30O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Ketosteroids
Family
  • Mammalian_Metabolite
Species
  • ketone; secondary alcohol
Biofunction
  • Hormones, Membrane component
Application
Source
  • Endogenous
Average Molecular Weight 290.440
Monoisotopic Molecular Weight 290.224579
Isomeric SMILES C[C@]12CCC(O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CCC2=O
Canonical SMILES CC12CCC(O)CC1CCC1C2CCC2(C)C1CCC2=O
KEGG Compound ID C00523 Link Image
BioCyc ID ANDROSTERONE Link Image
BiGG ID 35244 Link Image
Wikipedia Link Androsterone Link Image
METLIN ID 2797 Link Image
PubChem Compound 5879 Link Image
PubChem Substance 7885731 Link Image
ChEBI ID 16032 Link Image
CAS Registry Number 53-41-8
InChI Identifier InChI=1/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
Synthesis Reference Marker, Russell E. Androsterone. Journal of the American Chemical Society (1935), 57 1755-6.
Melting Point (Experimental) 185 oC
Experimental Water Solubility 0.012 mg/mL at 23 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 6.34e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity 3.69 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity 3.71 [Predicted by ALOGPS]; 4.3 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
  • Cytoplasm
  • endoplasmic reticulum
  • Extracellular
Biofluid Location Not Available
Tissue Location
Tissue References
Intestine
Most Tissues
Primarily Liver
Prostate
Testes
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Androgen and Estrogen Metabolism
HMDB Pathways
Name Androgen and Estrogen Metabolism
Image Show Link Image
KEGG Pathways
Name Androgen and Estrogen Metabolism
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SimCell Pathways
Name Androgen and Estrogen Metabolism
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Graph
SBML
General References
  1. Wikipedia Link Image