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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
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
C 19 H 28 O 3
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).
Chemical compound
7α-Hydroxydehydroepiandrosterone (7α-hydroxy-DHEA ; 7α-OH-DHEA ), also known as 3β,7α-dihydroxyandrost-5-ene-17-one , is an
endogenous ,
naturally occurring
steroid and a major
metabolite of
dehydroepiandrosterone (DHEA) that is formed by
CYP7B1 (steroid 7α-hydroxylase) in
tissues such as the
prostate gland and by
CYP3A4 in the
liver .
[1]
[2] The major
metabolic pathway of DHEA outside the liver is via 7-hydroxylation into 7α-OH-DHEA and
7β-OH-DHEA .
[3] 7α-OH-DHEA has weak
estrogenic activity,
selectively activating the
estrogen receptor
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
^
"Metabocard for 7α-Hydroxydehydroepiandrosterone (HMDB04611)" . Human Metabolome Database .
^
a
b Miller KK, Al-Rayyan N, Ivanova MM, Mattingly KA, Ripp SL, Klinge CM, Prough RA (2013).
"DHEA metabolites activate estrogen receptors alpha and beta" . Steroids . 78 (1): 15–25.
doi :
10.1016/j.steroids.2012.10.002 .
PMC
3529809 .
PMID
23123738 .
^ Li H, Liu HM, Ge W, Huang L, Shan L (2005). "Synthesis of 7alpha-hydroxy-dehydroepiandrosterone and 7beta-hydroxy-dehydroepiandrosterone". Steroids . 70 (14): 970–3.
doi :
10.1016/j.steroids.2005.07.006 .
PMID
16143359 .
S2CID
53294855 . he major metabolic pathway for DHEA in extra-hepatic tissues is via 7-hydroxylation [18], [19] and [20].
^
a
b Attal-Khémis S, Dalmeyda V, Michot JL, Roudier M, Morfin R (1998).
"Increased total 7 alpha-hydroxy-dehydroepiandrosterone in serum of patients with Alzheimer's disease" . J. Gerontol. A Biol. Sci. Med. Sci . 53 (2): B125–32.
doi :
10.1093/gerona/53a.2.b125 .
PMID
9520908 .
^
Neurosteroids and Brain Function . Academic Press. 12 December 2001. pp. 84–.
ISBN
978-0-08-054423-6 .
^ Ronald Ross Watson (22 July 2011).
DHEA in Human Health and Aging . CRC Press. pp. 437–.
ISBN
978-1-4398-3883-9 .
^
"World Anti-Doping Agency Prohibited List 2019" (PDF) .
External links
ER Tooltip Estrogen receptor
Agonists
Steroidal:
2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α-Hydroxy-DHEA
7α-Methylestradiol
7β-Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
11β-Methoxyestradiol
15α-Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
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16β-Hydroxyestrone
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (
alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17α-Ethynyl-3α-androstanediol
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SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
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ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
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