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Etiocholanedione
	; ;
Names;
	; IUPAC name; (5R,8R,9S,10S,13S,14S)-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-dione;
	Other names; Etiocholane-3,17-dione; 5β-Androstanedione; 5β-Androstane-3,17-dione;
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; ;
	; ; 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

^ ^a^b "Human Metabolome Database: Showing metabocard for Etiocholanedione (HMDB0003769)". hmdb.ca. Retrieved 2018-07-13..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}

^ ^a^b Bradlow HL, Murphy J, Byrne JJ (June 1999). "Immunological properties of dehydroepiandrosterone, its conjugates, and metabolites". Ann. N. Y. Acad. Sci. 876: 91–101. doi:10.1111/j.1749-6632.1999.tb07627.x. PMID 10415598.

^ ^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.

External links

Etiocholanedione (HMDB0003769) - Human Metabolome Database

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[HMDB-1] "Human Metabolome Database: Showing metabocard for Etiocholanedione (HMDB0003769)". hmdb.ca. Retrieved 2018-07-13..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}

[pmid10415598-2] Bradlow HL, Murphy J, Byrne JJ (June 1999). "Immunological properties of dehydroepiandrosterone, its conjugates, and metabolites". Ann. N. Y. Acad. Sci. 876: 91–101. doi:10.1111/j.1749-6632.1999.tb07627.x. PMID 10415598.

[McKeagMoeller2007-3] Douglas McKeag; James L. Moeller (2007). ACSM's Primary Care Sports Medicine. Lippincott Williams & Wilkins. pp. 616–. ISBN 978-0-7817-7028-6.

[Rippe2013-4] James M. Rippe (15 March 2013). Lifestyle Medicine, Second Edition. CRC Press. pp. 559–. ISBN 978-1-4398-4544-8.

[pmid8697065-5] 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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Rdxfbgrtj

Etiocholanedione

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Names

IUPAC name (5R,8R,9S,10S,13S,14S)-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
Other names Etiocholane-3,17-dione; 5β-Androstanedione; 5β-Androstane-3,17-dione
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
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