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16α-Hydroxy-DHEA

16α-Hydroxydehydroepiandrosterone (16α-hydroxy-DHEA or 16α-OH-DHEA) is an endogenous metabolite of dehydroepiandrosterone (DHEA). Both 16α-OH-DHEA and its 3β-sulfate ester, 16α-OH-DHEA-S, are intermediates in the biosynthesis of estriol from dehydroepiandrosterone (DHEA).[1] 16α-OH-DHEA has estrogenic activity.[2]

16α-Hydroxy-DHEA
Names
IUPAC name
3β,16α-Dihydroxyandrost-5-en-17-one
Systematic IUPAC name
(2R,3aS,3bR,7S,9aR,9bS,11aS)-3,7-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
Identifiers
  • 1232-73-1 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:27771 Y
ChemSpider
  • 92168 Y
  • 102030
UNII
  • WU2DU6GA72 Y
  • DTXSID90153892
  • InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,18-,19-/m0/s1 Y
    Key: QQIVKFZWLZJXJT-DNKQKWOHSA-N Y
  • InChI=1/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,18-,19-/m0/s1
    Key: QQIVKFZWLZJXJT-DNKQKWOHBQ
  • O=C3[C@]2(CC[C@@H]1[C@@]4(C(=C/C[C@H]1[C@@H]2C[C@H]3O)\C[C@@H](O)CC4)C)C
Properties
C19H28O3
Molar mass 304.42 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

See also edit

References edit

  1. ^ Raju U, Bradlow HL, Levitz M (1990). "Estriol-3-sulfate in human breast cyst fluid. Concentrations, possible origin, and physiologic implications". Ann. N. Y. Acad. Sci. 586: 83–7. doi:10.1111/j.1749-6632.1990.tb17793.x. PMID 2141460.
  2. ^ 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.



16α, hydroxy, dhea, 16α, hydroxydehydroepiandrosterone, 16α, hydroxy, dhea, 16α, dhea, endogenous, metabolite, dehydroepiandrosterone, dhea, both, 16α, dhea, sulfate, ester, 16α, dhea, intermediates, biosynthesis, estriol, from, dehydroepiandrosterone, dhea, 1. 16a Hydroxydehydroepiandrosterone 16a hydroxy DHEA or 16a OH DHEA is an endogenous metabolite of dehydroepiandrosterone DHEA Both 16a OH DHEA and its 3b sulfate ester 16a OH DHEA S are intermediates in the biosynthesis of estriol from dehydroepiandrosterone DHEA 1 16a OH DHEA has estrogenic activity 2 16a Hydroxy DHEA NamesIUPAC name 3b 16a Dihydroxyandrost 5 en 17 oneSystematic IUPAC name 2R 3aS 3bR 7S 9aR 9bS 11aS 3 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 oneIdentifiersCAS Number 1232 73 1 Y3D model JSmol Interactive imageChEBI CHEBI 27771 YChemSpider 92168 YPubChem CID 102030UNII WU2DU6GA72 YCompTox Dashboard EPA DTXSID90153892InChI InChI 1S C19H28O3 c1 18 7 5 12 20 9 11 18 3 4 13 14 18 6 8 19 2 15 13 10 16 21 17 19 22 h3 12 16 20 21H 4 10H2 1 2H3 t12 13 14 15 16 18 19 m0 s1 YKey QQIVKFZWLZJXJT DNKQKWOHSA N YInChI 1 C19H28O3 c1 18 7 5 12 20 9 11 18 3 4 13 14 18 6 8 19 2 15 13 10 16 21 17 19 22 h3 12 16 20 21H 4 10H2 1 2H3 t12 13 14 15 16 18 19 m0 s1Key QQIVKFZWLZJXJT DNKQKWOHBQSMILES O C3 C 2 CC C H 1 C 4 C C C C H 1 C H 2C C H 3O C C H O CC4 C CPropertiesChemical formula C19H28O3Molar mass 304 42 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesSee also edit15a Hydroxydehydroepiandrosterone 16a Hydroxyandrostenedione 16a Hydroxyestrone CetadiolReferences edit Raju U Bradlow HL Levitz M 1990 Estriol 3 sulfate in human breast cyst fluid Concentrations possible origin and physiologic implications Ann N Y Acad Sci 586 83 7 doi 10 1111 j 1749 6632 1990 tb17793 x PMID 2141460 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 nbsp This article about a steroid is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 16a Hydroxy DHEA amp oldid 1151751230, wikipedia, wiki, book, books, library,

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