16-Hydroxydehydroepiandrosterone

16-Hydroxydehydroepiandrosterone

Names
IUPAC name (3S,8R,9S,10R,13S,14S,16R)-3,16-Dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
Other names 3β,16α-Dihydroxyandrost-5-en-17-one
Identifiers
CAS Number	1232-73-1
ChEBI	CHEBI:27771
ChemSpider	92168
Jmol interactive 3D	Image
PubChem	102030
InChI 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 Key: QQIVKFZWLZJXJT-DNKQKWOHSA-N 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
SMILES 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
Chemical formula	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).
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Infobox references

16-Hydroxydehydroepiandrosterone (16-OH-DHEA) is an endogenous metabolite of dehydroepiandrosterone (DHEA). In its sulfonated form (16-Hydroxydehydroepiandrosterone sulfate or 16-OH DHEA-S), it is an intermediate in the biosynthesis of estriol.^[1]

16-OH-DHEA has estrogenic actions.^[2]

References

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.