fbpx
Wikipedia

Etiocholanedione

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]

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
  • 1229-12-5
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16985
ChEMBL
  • ChEMBL1230988
ChemSpider
  • 389114
DrugBank
  • DB07375
KEGG
  • C03772
  • 440114
UNII
  • 213MVW2TZD
  • DTXSID10153778
  • 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
  • C[C@]12CCC(=O)C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C
Properties
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).

References edit

  1. ^ a b "Human Metabolome Database: Showing metabocard for Etiocholanedione (HMDB0003769)". hmdb.ca. Retrieved 2018-07-13.
  2. ^ 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.
  3. ^ 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.
  4. ^ James M. Rippe (15 March 2013). Lifestyle Medicine, Second Edition. CRC Press. pp. 559–. ISBN 978-1-4398-4544-8.
  5. ^ 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 edit

  • Etiocholanedione (HMDB0003769) - Human Metabolome Database


etiocholanedione, also, known, androstanedione, etiocholane, dione, naturally, occurring, etiocholane, androstane, steroid, endogenous, metabolite, androgens, like, testosterone, dihydrotestosterone, dehydroepiandrosterone, dhea, androstenedione, epimer, andro. Etiocholanedione also known as 5b androstanedione or as etiocholane 3 17 dione is a naturally occurring etiocholane 5b androstane steroid and an endogenous metabolite of androgens like testosterone dihydrotestosterone dehydroepiandrosterone DHEA and androstenedione 1 It is the C5 epimer of androstanedione 5a androstanedione 1 Although devoid of androgenic activity like other 5b 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 Etiocholanedione NamesIUPAC name 5b Androstane 3 17 dioneSystematic IUPAC name 3aS 3bR 5aR 9aS 9bS 11aS 9a 11a Dimethyltetradecahydro 1H cyclopenta a phenanthrene 1 7 3bH dioneOther names Etiocholane 3 17 dione 5b AndrostanedioneIdentifiersCAS Number 1229 12 53D model JSmol Interactive imageChEBI CHEBI 16985ChEMBL ChEMBL1230988ChemSpider 389114DrugBank DB07375KEGG C03772PubChem CID 440114UNII 213MVW2TZDCompTox Dashboard EPA DTXSID10153778InChI 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 s1Key RAJWOBJTTGJROA QJISAEMRSA NSMILES C C 12CCC O C C H 1CC C H 3 C H 2CC C 4 C H 3CCC4 O CPropertiesChemical formula C 19H 28O 2Molar mass 288 431 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesReferences 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 amp 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 editEtiocholanedione HMDB0003769 Human Metabolome Database nbsp This article about a steroid is a stub You can help Wikipedia by expanding it vte nbsp This biochemistry article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Etiocholanedione amp oldid 1189000214, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.