Androstenediol sulfate

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Androstenediol sulfate
Androstenediol 3-sulfate.svg
Names
Preferred IUPAC name
(1S,3aS,3bR,7S,9aR,9bS,11aS)-1-Hydroxy-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-yl hydrogen sulfate
Other names
Androst-5-ene-3β,17β-diol 3β-sulfate; 3β,17β-Dihydroxyandrost-5-ene 3β-sulfate; A5 sulfate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C19H30O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-17,20H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,17-,18-,19-/m0/s1
    Key: HXJFCUUBVWOORF-LOVVWNRFSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC=C4[C@@]3(CC[C@@H](C4)OS(=O)(=O)O)C
Properties
C19H30O5S
Molar mass 370.50 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Androstenediol sulfate, also known as androst-5-ene-3β,17β-diol 3β-sulfate, is an endogenous, naturally occurring steroid and a urinary metabolites of androstenediol.[1] It is a steroid sulfate which is formed from sulfation of androstenediol by steroid sulfotransferase and can be desulfated back into androstenediol by steroid sulfatase.[1]

See also[edit]

References[edit]

  1. ^ a b Mueller JW, Gilligan LC, Idkowiak J, Arlt W, Foster PA (2015). "The Regulation of Steroid Action by Sulfation and Desulfation". Endocr. Rev. 36 (5): 526–63. doi:10.1210/er.2015-1036. PMC 4591525. PMID 26213785.