fbpx
Wikipedia

Epietiocholanolone

May 04, 2024

Epietiocholanolone, also known as 3β-hydroxy-5β-androstan-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.[1][2][3] The metabolic pathway is testosterone to 5β-dihydrotestosterone (via 5β-reductase),[1] 5β-dihydrotestosterone to 3β,5β-androstanediol (via 3β-hydroxysteroid dehydrogenase), and 3β,5β-androstanediol to epietiocholanolone (via 17β-hydroxysteroid dehydrogenase).[3] Epietiocholanolone can also be formed directly from 5β-androstanedione (via 3β-hydroxysteroid dehydrogenase).[3][4] It is glucuronidated and sulfated in the liver and excreted in urine.[3][5]

Epietiocholanolone
Names
IUPAC name
3β-Hydroxy-5β-androstan-17-one
Systematic IUPAC name
(3aS,3bR,5aR,7S,9aS,9bS,11aS)-7-Hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-one
Other names
5β-Androstan-3β-ol-17-one; Etiocholan-3β-ol-17-one
Identifiers
  • 571-31-3
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:89524
ChEMBL
  • ChEMBL260526
ChemSpider
  • 216866
  • 247732
UNII
  • C1751JYC6P
  • DTXSID20289698
  • 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
  • C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
Properties
C19H30O2
Molar mass 290.447 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

See also edit

References edit

  1. ^ a b Arun Nagrath; Narendra Malhotra; Seth Shikha (31 July 2012). Progress in Obstetrics & Gynecology. JP Medical Ltd. pp. 265–. ISBN 978-93-5025-779-1.
  2. ^ J. Horsky; J. Presl (6 December 2012). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 107–. ISBN 978-94-009-8195-9.
  3. ^ a b c d MORFIN Robert (20 December 2010). Les stéroïdes naturels de A à Z. Lavoisier. pp. 428–. ISBN 978-2-7430-1918-1.
  4. ^ Hugh L. J. Makin; D.B. Gower (4 June 2010). Steroid Analysis. Springer Science & Business Media. pp. 462–. ISBN 978-1-4020-9775-1.
  5. ^ Hauser B, Deschner T, Boesch C (2008). "Development of a liquid chromatography-tandem mass spectrometry method for the determination of 23 endogenous steroids in small quantities of primate urine". J. Chromatogr. B. 862 (1–2): 100–12. doi:10.1016/j.jchromb.2007.11.009. PMID 18054529.


 

This article about a steroid is a stub. You can help Wikipedia by expanding it.

May 04, 2024
epietiocholanolone, also, known, hydroxy, androstan, etiocholan, etiocholane, androstane, steroid, well, inactive, metabolite, testosterone, that, formed, liver, metabolic, pathway, testosterone, dihydrotestosterone, reductase, dihydrotestosterone, androstaned. Epietiocholanolone also known as 3b hydroxy 5b androstan 17 one or as etiocholan 3b ol 17 one is an etiocholane 5b androstane steroid as well as an inactive metabolite of testosterone that is formed in the liver 1 2 3 The metabolic pathway is testosterone to 5b dihydrotestosterone via 5b reductase 1 5b dihydrotestosterone to 3b 5b androstanediol via 3b hydroxysteroid dehydrogenase and 3b 5b androstanediol to epietiocholanolone via 17b hydroxysteroid dehydrogenase 3 Epietiocholanolone can also be formed directly from 5b androstanedione via 3b hydroxysteroid dehydrogenase 3 4 It is glucuronidated and sulfated in the liver and excreted in urine 3 5 Epietiocholanolone Names IUPAC name 3b Hydroxy 5b androstan 17 one Systematic IUPAC name 3aS 3bR 5aR 7S 9aS 9bS 11aS 7 Hydroxy 9a 11a dimethylhexadecahydro 1H cyclopenta a phenanthren 1 one Other names 5b Androstan 3b ol 17 one Etiocholan 3b ol 17 one Identifiers CAS Number 571 31 3 3D model JSmol Interactive image ChEBI CHEBI 89524 ChEMBL ChEMBL260526 ChemSpider 216866 PubChem CID 247732 UNII C1751JYC6P CompTox Dashboard EPA DTXSID20289698 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 s1Key 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 C 19H 30O 2 Molar mass 290 447 g mol 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesSee also editAndrosterone Epiandrosterone EtiocholanoloneReferences edit a b Arun Nagrath Narendra Malhotra Seth Shikha 31 July 2012 Progress in Obstetrics amp Gynecology JP Medical Ltd pp 265 ISBN 978 93 5025 779 1 J Horsky J Presl 6 December 2012 Ovarian Function and its Disorders Diagnosis and Therapy Springer Science amp Business Media pp 107 ISBN 978 94 009 8195 9 a b c d MORFIN Robert 20 December 2010 Les steroides naturels de A a Z Lavoisier pp 428 ISBN 978 2 7430 1918 1 Hugh L J Makin D B Gower 4 June 2010 Steroid Analysis Springer Science amp Business Media pp 462 ISBN 978 1 4020 9775 1 Hauser B Deschner T Boesch C 2008 Development of a liquid chromatography tandem mass spectrometry method for the determination of 23 endogenous steroids in small quantities of primate urine J Chromatogr B 862 1 2 100 12 doi 10 1016 j jchromb 2007 11 009 PMID 18054529 nbsp This article about a steroid is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Epietiocholanolone amp oldid 1188996281, 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.