16α-Hydroxy-DHEA sulfate

16α-Hydroxydehydroepiandrosterone sulfate (16α-OH-DHEA-S), also known as 16α-hydroxy-17-oxoandrost-5-en-3β-yl sulfate, is an endogenous, naturally occurring steroid and a metabolic intermediate in the production of estriol from dehydroepiandrosterone (DHEA) during pregnancy.[1][2] It is the C3β sulfate ester of 16α-hydroxy-DHEA.[3][4]

16α-Hydroxy-DHEA sulfate
Names
IUPAC name
16α-Hydroxy-17-oxoandrost-5-en-3β-yl hydrogen sulfate
Systematic IUPAC name
(2R,3aS,3bR,7S,9aR,9bS,11aS)-2-Hydroxy-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
16α-Hydroxy-17-oxoandrost-5-en-3β-yl sulfate; 16α-OH-DHEA-S
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C19H28O6S/c1-18-7-5-12(25-26(22,23)24)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(20)17(19)21/h3,12-16,20H,4-10H2,1-2H3,(H,22,23,24)/t12-,13+,14-,15-,16+,18-,19-/m0/s1
    Key: ALBNSVAJDFJRKQ-DNKQKWOHSA-N
  • C[C@]12CC[C@@H](CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3C[C@H](C4=O)O)C)OS(=O)(=O)O
Properties
C19H28O6S
Molar mass 384.49 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Jerome F. Strauss, III; Robert L. Barbieri (13 September 2013). Yen and Jaffe's Reproductive Endocrinology. Elsevier Health Sciences. pp. 256–. ISBN 978-1-4557-2758-2.
  2. Hiroshi Yamazaki (23 June 2014). Fifty Years of Cytochrome P450 Research. Springer. pp. 385–. ISBN 978-4-431-54992-5.
  3. Mike S. Lee (8 May 2012). Mass Spectrometry Handbook. John Wiley & Sons. pp. 320–. ISBN 978-0-470-53673-5.
  4. Shlomo Melmed; Kenneth S. Polonsky; P. Reed Larsen; Henry M. Kronenberg (30 November 2015). Williams Textbook of Endocrinology. Elsevier Health Sciences. pp. 839–. ISBN 978-0-323-29738-7.



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