3β-Etiocholanediol

3β-Etiocholanediol, or epietiocholanediol, also known as 3β,5β-androstanediol or as etiocholane-3β,17β-diol, is a naturally occurring etiocholane (5β-androstane) steroid and an endogenous metabolite of testosterone. It is formed from 5β-dihydrotestosterone (after 5β-reduction of testosterone) and is transformed into epietiocholanolone.[1]

3β-Etiocholanediol

Names
IUPAC name (3S,5R,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
Other names Epietiocholanediol; 5β-Androstane-3β,17β-diol; Etiocholane-3β,17β-diol
Identifiers
3D model (JSmol)	Interactive image
ChEBI	CHEBI:36715
ChEMBL	ChEMBL1908037
ChemSpider	8097750
PubChem CID	9922115
UNII	N5O0J576TA
InChI InChI=1S/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14+,15+,16+,17+,18+,19+/m1/s1 Key: CBMYJHIOYJEBSB-VXZRPZIYSA-N
SMILES C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C)O
Properties
Chemical formula	C19H32O2
Molar mass	292.463 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

• 3α-Etiocholanediol
• 3α-Androstanediol
• 3β-Androstanediol

References

1. Miller AM, Dorfman RI (March 1948). "Metabolism of the steroid hormones; the isolation of etiocholanediol-3(alpha), 17(alpha) from human urine". Endocrinology. 42 (3): 174. doi:10.1210/endo-42-3-174. PMID 18914211.