11β-Hydroxyandrostenedione

11β-Hydroxyandrostenedione (11β-OHA4), also known as 11β-hydroxyandrost-4-ene-3,17-dione, is an endogenous, naturally occurring steroid and androgen prohormone that is produced primarily, if not exclusively, in the adrenal glands.[1] It is closely related to adrenosterone (11-ketoandrostenedione; 11-KA4), 11-ketotestosterone (11-KT), and 11-ketodihydrotestosterone (11-KDHT), which are also produced in the adrenal glands.[1]

11β-Hydroxyandrostenedione

Names
IUPAC name (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
Other names 11β-Hydroxy-4-androstenedione; 11β-Hydroxyandrost-4-ene-3,17-dione; 11β-OHA4
Identifiers
CAS Number	382-44-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27967
ChEMBL	ChEMBL2311170
ChemSpider	84958
PubChem CID	94141
UNII	41G81C896T
CompTox Dashboard (EPA)	DTXSID8040931
InChI InChI=1S/C19H26O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15-,17+,18-,19-/m0/s1 Key: WSCUHXPGYUMQEX-KCZNZURUSA-N
SMILES C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CCC4=O)C)O
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

See also

• 4-Androstenedione

References

1. Pretorius, Elzette; Arlt, Wiebke; Storbeck, Karl-Heinz (2016). "A new dawn for androgens: Novel lessons from 11-oxygenated C19 steroids" (PDF). Molecular and Cellular Endocrinology. 441: 76–85. doi:10.1016/j.mce.2016.08.014. ISSN 0303-7207. PMID 27519632.