Etiocholanedione

Etiocholanedione
Names
	IUPAC name 5β-Androstane-3,17-dione
	Systematic IUPAC name (3aS,3bR,5aR,9aS,9bS,11aS)-9a,11a-Dimethyltetradecahydro-1H-cyclopenta[a]phenanthrene-1,7(3bH)-dione
	Other names Etiocholane-3,17-dione; 5β-Androstanedione
Identifiers
CAS Number	1229-12-5;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16985;
ChEMBL	ChEMBL1230988;
ChemSpider	389114;
DrugBank	DB07375;
KEGG	C03772;
PubChem CID	440114;
UNII	213MVW2TZD;
CompTox Dashboard (EPA)	DTXSID10153778 ;
	InChI InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14+,15+,16+,18+,19+/m1/s1 Key: RAJWOBJTTGJROA-QJISAEMRSA-N;
	SMILES C[C@]12CCC(=O)C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C;
Properties
Chemical formula	C19H28O2
Molar mass	288.431 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Etiocholanedione, also known as 5β-androstanedione or as etiocholane-3,17-dione, is a naturally occurring etiocholane (5β-androstane) steroid and an endogenous metabolite of androgens like testosterone, dihydrotestosterone, dehydroepiandrosterone (DHEA), and androstenedione.^[1] It is the C5 epimer of androstanedione (5α-androstanedione).^[1] Although devoid of androgenic activity like other 5β-reduced steroids, etiocholanedione has some biological activity of its own.^[2]^[3] The compound has been found to possess potent haematopoietic effects in a variety of models.^[2] In addition, it has been found to promote weight loss in animals and in a double-blind, placebo-controlled clinical study in humans conducted in 1993.^[3]^[4] These effects are said to be similar to those of DHEA.^[5] Unlike DHEA however, etiocholanedione cannot be metabolized further into steroid hormones like androgens and estrogens.^[5]

References[edit]

^ ^a ^b "Human Metabolome Database: Showing metabocard for Etiocholanedione (HMDB0003769)". hmdb.ca. Retrieved 2018-07-13.
^ ^a ^b Bradlow HL, Murphy J, Byrne JJ (June 1999). "Immunological properties of dehydroepiandrosterone, its conjugates, and metabolites". Ann. N. Y. Acad. Sci. 876 (1): 91–101. Bibcode:1999NYASA.876...91B. doi:10.1111/j.1749-6632.1999.tb07627.x. PMID 10415598. S2CID 46148045.
^ ^a ^b Douglas McKeag; James L. Moeller (2007). ACSM's Primary Care Sports Medicine. Lippincott Williams & Wilkins. pp. 616–. ISBN 978-0-7817-7028-6.
^ James M. Rippe (15 March 2013). Lifestyle Medicine, Second Edition. CRC Press. pp. 559–. ISBN 978-1-4398-4544-8.
^ ^a ^b Clore JN (November 1995). "Dehydroepiandrosterone and body fat". Obes. Res. 3 (Suppl 4): 613S–616S. doi:10.1002/j.1550-8528.1995.tb00234.x. PMID 8697065.

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Names

IUPAC name 5β-Androstane-3,17-dione
Systematic IUPAC name (3aS,3bR,5aR,9aS,9bS,11aS)-9a,11a-Dimethyltetradecahydro-1H-cyclopenta[a]phenanthrene-1,7(3bH)-dione
Other names Etiocholane-3,17-dione; 5β-Androstanedione
Identifiers
CAS Number	1229-12-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16985
ChEMBL	ChEMBL1230988
ChemSpider	389114
DrugBank	DB07375
KEGG	C03772
PubChem CID	440114
UNII	213MVW2TZD
CompTox Dashboard (EPA)	DTXSID10153778
InChI InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14+,15+,16+,18+,19+/m1/s1 Key: RAJWOBJTTGJROA-QJISAEMRSA-N
SMILES C[C@]12CCC(=O)C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C
Properties
Chemical formula	C₁₉H₂₈O₂
Molar mass	288.431 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references