7α-Hydroxy-DHEA

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7α-Hydroxy-DHEA
Names
IUPAC name
3β,7α-Dihydroxyandrost-5-ene-17-one
Systematic IUPAC name
(3aS,3bR,4S,7S,9aR,9bS,11aS)-4,7-Dihydroxy-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-one
Other names
7α-OH-DHEA; Androst-5-en-3β,7α-diol-17-one
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15+,17-,18-,19-/m0/s1
    Key: OLPSAOWBSPXZEA-JIEICEMKSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)[C@@H](C=C4[C@@]3(CC[C@@H](C4)O)C)O
Properties
C19H28O3
Molar mass 304.430 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

7α-Hydroxydehydroepiandrosterone (7α-hydroxy-DHEA; 7α-OH-DHEA), also known as 3β,7α-dihydroxyandrost-5-ene-17-one, is an

ERβ.[2] In addition, 7α-OH-DHEA may be responsible for the known antiglucocorticoid effects of DHEA.[4][5]

Serum levels of 7α-OH-DHEA have been found to be significantly elevated in patients with Alzheimer's disease.[4] It is unclear what significance this may have, if any.[6]

7α-OH-DHEA is on the World Anti-Doping Agency list of prohibited substances in sporting.[7]

See also

References

  1. ^ "Metabocard for 7α-Hydroxydehydroepiandrosterone (HMDB04611)". Human Metabolome Database.
  2. ^
    PMID 23123738
    .
  3. S2CID 53294855
    . he major metabolic pathway for DHEA in extra-hepatic tissues is via 7-hydroxylation [18], [19] and [20].
  4. ^
    PMID 9520908
    .
  5. ISBN 978-0-08-054423-6
    .
  6. ISBN 978-1-4398-3883-9
    .
  7. ^ "World Anti-Doping Agency Prohibited List 2019" (PDF).

External links

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