Epietiocholanolone

Epietiocholanolone

Names
IUPAC name (3S,5R,8R,9S,10S,13S,14S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
Other names 5β-Androstan-3β-ol-17-one; Etiocholan-3β-ol-17-one
Identifiers
CAS Number	571-31-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:89524
ChemSpider	216866
PubChem CID	247732
UNII	C1751JYC6P
InChI InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14+,15+,16+,18+,19+/m1/s1 Key: QGXBDMJGAMFCBF-XRJZGPCZSA-N
SMILES C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
Properties
Chemical formula	C19H30O2
Molar mass	290.45 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

Epietiocholanolone, also known as 5β-androstan-3β-ol-17-one or as etiocholan-3β-ol-17-one, is an etiocholane (5β-androstane) steroid as well as an inactive metabolite of testosterone that is formed in the liver. The metabolic pathway is testosterone to 5β-dihydrotestosterone (via 5β-reductase), 5β-dihydrotestosterone to 3β,5β-androstanediol (via 3β-hydroxysteroid dehydrogenase), and 3β,5β-androstanediol to epietiocholanolone (via 17β-hydroxysteroid dehydrogenase). Epietiocholanolone can also be formed directly from 5β-androstanedione (via 3β-hydroxysteroid dehydrogenase). It is glucuronidated and sulfated in the liver and excreted in urine.