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
CAS Number	65535-18-4;
3D model (JSmol)	Interactive image;
ChemSpider	20558912;
PubChem CID	16727166;
CompTox Dashboard (EPA)	DTXSID701335922 ;
	InChI 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;
	SMILES 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
Chemical formula	C25H40O8
Molar mass	468.587 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3α-Androstanediol glucuronide (3α-ADG) is a metabolite formed from human androgens; compounds involved in the development and maintenance of sexual characteristics. It is formed by the glucuronidation of dihydrotestosterone,^[1] and has been proposed as means of measuring androgenic activity.^[2]

In women the adrenal steroids, dehydroepiandrosterone sulfate, androstenedione and dehydroepiandrosterone 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 of 5α-reductase activity (testosterone and 3α-androstanediol to dihydrotestosterone) in the skin. Concentrations of 3α-ADG are associated with the level of cutaneous androgen metabolism.

References

^ 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.
^ ^a ^b Labrie 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.
^ 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.

[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.

[:0-2] Labrie 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.

[1]

[2]

[3]

Androstanediol glucuronide

See also

References

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