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Chemical Compound Review

Androst-16-ene     (8R,9S,10S,13S,14S)-10,13- dimethyl-2,3,4,5...

Synonyms: AG-K-05979, CHEBI:37925, CTK0I2006, AR-1H7286, AR-1H7287, ...
 
 
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Disease relevance of Androst-16-ene

  • In incubations containing 5,16-androstadien-3-ol, mixed populations of Corynebacterium spp., isolated from the axilla, could generate many different 16-androstene metabolites, several of which were odorous [1].
 

High impact information on Androst-16-ene

 

Biological context of Androst-16-ene

  • Based on detection of these metabolites, a metabolic map for axillary corynebacterial 16-androstene biotransformations was proposed, detailing potential enzyme activities [1].
  • Previous studies from this laboratory have suggested that the 3 beta-HSD-I reactions in the androgen and 16-androstene biosynthetic pathways may be catalysed by different enzymes with selective substrate specificities [3, 4] [6].
  • The high concentration of 16-androstene steroids in boar glands was correlated with the presence of large amounts of binding protein for these steroids in the glands; smaller amounts of the binding protein were detected in female glands [7].
 

Anatomical context of Androst-16-ene

 

Associations of Androst-16-ene with other chemical compounds

 

Gene context of Androst-16-ene

References

  1. Microbial pathways leading to steroidal malodour in the axilla. Austin, C., Ellis, J. J. Steroid Biochem. Mol. Biol. (2003) [Pubmed]
  2. Intermediates in 16-androstene biosynthesis in neonatal porcine testis. Kwan, T.K., Honour, J.W., Taylor, N.F., Gower, D.B. FEBS Lett. (1984) [Pubmed]
  3. Identification of 16-dehydropregnenolone as an intermediate in 16-androstene biosynthesis in neonatal porcine testicular microsomes. Kwan, T.K., Taylor, N.F., Watson, D., Gower, D.B. FEBS Lett. (1984) [Pubmed]
  4. A novel polymorphism in the 5' untranslated region of the porcine cytochrome b5 (CYB5) gene is associated with decreased fat androstenone level. Lin, Z., Lou, Y., Peacock, J., Squires, E.J. Mamm. Genome (2005) [Pubmed]
  5. Synthesis of free and sulphoconjugated 16-androstene steroids by the Leydig cells of the mature domestic boar. Sinclair, P.A., Squires, E.J., Raeside, J.I., Renaud, R. J. Steroid Biochem. Mol. Biol. (2005) [Pubmed]
  6. Differential effects of trilostane and cyanoketone on the 3 beta-hydroxysteroid dehydrogenase-isomerase reactions in androgen and 16-androstene biosynthetic pathways in the pig testis. Cooke, G.M. J. Steroid Biochem. Mol. Biol. (1996) [Pubmed]
  7. Sexual dimorphism involving steroidal pheromones and their binding protein in the submaxillary salivary gland of the Göttingen miniature pig. Booth, W.D. J. Endocrinol. (1984) [Pubmed]
  8. Purification and characterization of pheromaxein, the porcine steroid-binding protein. A member of the secretoglobin superfamily. Austin, C.J., Emberson, L., Nicholls, P. Eur. J. Biochem. (2004) [Pubmed]
  9. Metabolism of the 16-androstene steroids in primary cultured porcine hepatocytes. Sinclair, P.A., Hancock, S., Gilmore, W.J., Squires, E.J. J. Steroid Biochem. Mol. Biol. (2005) [Pubmed]
  10. The isolation and characterization of the soluble and membrane-bound porcine cytochrome b5 cDNAs. VanDerMark, P.K., Steggles, A.W. Biochem. Biophys. Res. Commun. (1997) [Pubmed]
  11. Applications of gas chromatography-mass spectrometry in the study of androgen and odorous 16-androstene metabolism by human axillary bacteria. Mallet, A.I., Holland, K.T., Rennie, P.J., Watkins, W.J., Gower, D.B. J. Chromatogr. (1991) [Pubmed]
  12. Studies of 16-androstene steroid biosynthesis and binding in human testis. Kwan, T.K., Kraevskaya, M.A., Trafford, D.J., Makin, H.L., Gower, D.B. Biochem. Soc. Trans. (1992) [Pubmed]
  13. Association of cytochrome b5 with 16-androstene steroid synthesis in the testis and accumulation in the fat of male pigs. Davis, S.M., Squires, E.J. J. Anim. Sci. (1999) [Pubmed]
  14. Comparison of androst-16-ene steroid levels determined by a colorimetric assay with boar taint estimated by a trained sensory panel. Squires, E.J., Gullett, E.A., Fisher, K.R., Partlow, G.D. J. Anim. Sci. (1991) [Pubmed]
  15. Breed differences in boar taint: relationship between tissue levels boar taint compounds and sensory analysis of taint. Xue, J., Dial, G.D., Holton, E.E., Vickers, Z., Squires, E.J., Lou, Y., Godbout, D., Morel, N. J. Anim. Sci. (1996) [Pubmed]
  16. Testicular sulfoconjugation of the 16-androstene steroids by hydroxysteroid sulfotransferase: its effect on the concentrations of 5alpha-androstenone in plasma and fat of the mature domestic boar. Sinclair, P.A., Squires, E.J. J. Anim. Sci. (2005) [Pubmed]
 
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