Dehydroepiandrosterone sulfate

This article is about DHEA sulfate as a hormone. For its use as a medication, see Prasterone sulfate.
Dehydroepiandrosterone sulfate
Names
IUPAC name
17-Oxoandrost-5-en-3β-yl hydrogen sulfate
Systematic IUPAC name
(3aS,3bR,7S,9aR,9bS,11aS)-9a,11a-Dimethyl-1-oxo-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
Androstenolone sulfate; Prasterone sulfate; Androst-5-en-3β-ol-17-one 3β-sulfate
Identifiers
3D model (JSmol)
Abbreviations DHEA sulfate; DHEA-S; DHEAS
ChemSpider
UNII
  • InChI=1S/C19H28O5S/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/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1 ☒N
    Key: CZWCKYRVOZZJNM-USOAJAOKSA-N ☒N
  • InChI=1/C19H28O5S/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/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1
    Key: CZWCKYRVOZZJNM-USOAJAOKBK
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)OS(=O)(=O)O)C
Properties
C19H28O5S
Molar mass 368.49 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dehydroepiandrosterone sulfate, abbreviated as DHEA sulfate or DHEA-S, also known as androstenolone sulfate, is an endogenous androstane steroid that is produced by the adrenal cortex.[1] It is the 3β-sulfate ester and a metabolite of dehydroepiandrosterone (DHEA) and circulates in far greater relative concentrations than DHEA.[2] The steroid is hormonally inert and is instead an important neurosteroid and neurotrophin.[2]

  1. ^ Cite error: The named reference Erkkola2006 was invoked but never defined (see the help page).
  2. ^ a b Cite error: The named reference pmid26908835 was invoked but never defined (see the help page).