Androstanediol glucuronide

Androstanediol glucuronide

Names
IUPAC name (3α,5α,17β)-17-Hydroxyandrostan-3-yl β-D-glucopyranosiduronic acid
Identifiers
ChemSpider	20558912
Jmol interactive 3D	Image
PubChem	16727166
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	468.59 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

Androstanediol glucuronide (ADG) is a metabolite of dihydrotestosterone and testosterone.^[1] In women the adrenal steroids, dehydroepiandrosterone sulfate, androstenedione and dehydroepiandrosterone are the major precursors of plasma ADG, accounting for almost the totality of circulating ADG. ADG levels decrease significantly with age.^[2] Androstanediol glucuronide is used as a marker of target tissue cellular action. ADG correlates with level of 5 alpha reductase activity (testosterone and androstanediol to dihydrotestosterone) in the skin. ADG is a measure of cutaneous androgen metabolism. it reflects specific type of liver function and the impact of major precursor derived from adrenal glands.^[3]

See also

• 3α-Androstanediol
• 3β-Androstanediol

References

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. 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.
3. http://www.hormonetestingmd.com/product_p/androstanediol-glucuronide.htm[]