16α-Hydroxyandrostenedione

16α-Hydroxyandrostenedione

Names
IUPAC name (8R,9S,10R,13S,14S,16R)-16-Hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
Other names 16α-Hydroxyandrost-4-ene-3,17-dione; 16α-OH-A4
Identifiers
CAS Number	63-02-5
3D model (Jmol)	Interactive image
ChEBI	CHEBI:27582
ChEMBL	ChEMBL1908014
ChemSpider	389474
PubChem	440574
UNII	JN8H7214IR
InChI InChI=1S/C19H26O3/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/h9,13-16,21H,3-8,10H2,1-2H3/t13-,14+,15+,16-,18+,19+/m1/s1 Key: SSBCZTXGVMMZOT-NBBHSKLNSA-N
SMILES C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3C[C@H](C4=O)O)C
Properties
Chemical formula	C19H26O3
Molar mass	302.414 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

16α-Hydroxyandrostenedione (16α-OH-A4), also known as 16α-hydroxyandrost-4-ene-3,17-dione, is an endogenous and naturally occurring steroid and metabolic intermediate in the biosynthesis of estriol during pregnancy.^[1][2][3] It is produced from dehydroepiandrosterone (DHEA), which is converted into 16α-hydroxy-DHEA sulfate, then desulfated and aromatized into 16α-hydroxyestrone, and finally converted into estriol by 17β-hydroxysteroid dehydrogenase.^[1][2]

See also

• Androstenedione
• 11β-Hydroxyandrostenedione

References

1. Rodney Rhoades; David R. Bell (2009). Medical Physiology: Principles for Clinical Medicine. Lippincott Williams & Wilkins. pp. 713–714. ISBN 978-0-7817-6852-8.
2. Charles Graham (2 December 2012). Reproductive Biology of the Great Apes: Comparative and Biomedical Perspectives. Elsevier. pp. 56–. ISBN 978-0-323-14971-6.
3. Vitamins and Hormones. Academic Press. 7 September 2005. pp. 282–. ISBN 978-0-08-045978-3.