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 [(3S,8R,9S,10R,13S,14S,16R)-16-Hydroxy-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate
Other names 16α-Hydroxy-17-oxoandrost-5-en-3β-yl sulfate; 16α-OH-DHEA-S
Identifiers
3D model (JSmol)	Interactive image
ChEBI	CHEBI:87538
ChemSpider	24850136
PubChem CID	20848950
InChI 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
SMILES 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
Chemical formula	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

• Pregnenolone sulfate
• Dehydroepiandrosterone sulfate
• 15α-Hydroxy-DHEA sulfate
• 16α-Hydroxyandrostenedione
• 16α-Hydroxyestrone
• Estrone sulfate

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.