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Androstanediol glucuronide

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(Redirected from3α-Androstanediol glucuronide)

Androstanediol glucuronide
Names
IUPAC name
17β-Hydroxy-5α-androstan-3α-yl β-D-glucopyranosiduronic acid
Systematic IUPAC name
(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-{[(1S,3aS,3bR,5aS,7R,9aS,9bS,11aS)-1-hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl]oxy}oxane-2-carboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C25H40O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-21,23,26-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1
    Key: GYNWSIBKBBWJJW-WWLGJQRMSA-N
  • InChI=1/C25H40O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-21,23,26-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1
    Key: GYNWSIBKBBWJJW-WWLGJQRMBJ
  • C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O
Properties
C25H40O8
Molar mass468.587 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
This articlemay be too technical for most readers to understand. Pleasehelp improve it tomake it understandable to non-experts, without removing the technical details.(December 2014) (Learn how and when to remove this message)

3α-Androstanediol glucuronide (3α-ADG) is ametabolite formed from humanandrogens; compounds involved in the development and maintenance of sexual characteristics. It is formed by theglucuronidation ofdihydrotestosterone,[1] and has been proposed as means of measuring androgenic activity.[2]

In women the adrenal steroids,dehydroepiandrosterone sulfate,androstenedione anddehydroepiandrosterone are the major precursors of plasma 3α-ADG, accounting for almost the totality of circulating 3α-ADG. Levels of 3α-ADG decrease significantly with age.[3]

3α-ADG is used as a marker of target tissue cellular action.[2] 3α-ADG correlates with level of5α-reductase activity (testosterone and3α-androstanediol to dihydrotestosterone) in the skin. Concentrations of 3α-ADG are associated with the level of cutaneous androgen metabolism.

See also

[edit]

References

[edit]
  1. ^Moghissi E, Ablan F, Horton R (September 1984). "Origin of plasma androstanediol glucuronide in men".The Journal of Clinical Endocrinology and Metabolism.59 (3):417–21.doi:10.1210/jcem-59-3-417.PMID 6746859.
  2. ^abLabrie F, Bélanger A, Bélanger P, Bérubé R, Martel C, Cusan L, Gomez J, Candas B, Castiel I, Chaussade V, Deloche C, Leclaire J (June 2006)."Androgen glucuronides, instead of testosterone, as the new markers of androgenic activity in women".The Journal of Steroid Biochemistry and Molecular Biology.99 (4–5):182–188.doi:10.1016/j.jsbmb.2006.02.004.PMID 16621522.S2CID 31765384.
  3. ^Vermeulen A, Giagulli VA (November 1991). "Physiopathology of plasma androstanediol-glucuronide".The Journal of Steroid Biochemistry and Molecular Biology.39 (5B):829–33.doi:10.1016/0960-0760(91)90032-z.PMID 1835405.S2CID 46135916.
Precursors
Corticosteroids
Glucocorticoids
Mineralocorticoids
Sex steroids
Androgens
Estrogens
Progestogens
Neurosteroids
Others
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