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Epietiocholanolone

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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
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)	DTXSID601024073 DTXSID20289698, DTXSID601024073
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/s1 Key: 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	C₁₉H₃₀O₂
Molar mass	290.447 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Epietiocholanolone, also known as3β-hydroxy-5β-androstan-17-one or asetiocholan-3β-ol-17-one, is anetiocholane (5β-androstane)steroid as well as an inactivemetabolite oftestosterone that is formed in theliver.^[1]^[2]^[3] Themetabolic pathway is testosterone to5β-dihydrotestosterone (via5β-reductase),^[1] 5β-dihydrotestosterone to3β,5β-androstanediol (via3β-hydroxysteroid dehydrogenase), and 3β,5β-androstanediol to epietiocholanolone (via17β-hydroxysteroid dehydrogenase).^[3] Epietiocholanolone can also be formed directly from5β-androstanedione (via 3β-hydroxysteroid dehydrogenase).^[3]^[4] It isglucuronidated andsulfated in the liver andexcreted inurine.^[3]^[5]

References

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^^a ^bArun Nagrath; Narendra Malhotra; Seth Shikha (31 July 2012).Progress in Obstetrics & 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 & Business Media. pp. 107–.ISBN 978-94-009-8195-9.
^^a ^b ^c ^dMORFIN Robert (20 December 2010).Les stéroïdes naturels de A à Z. Lavoisier. pp. 428–.ISBN 978-2-7430-1918-1.
^Hugh L. J. Makin; D.B. Gower (4 June 2010).Steroid Analysis. Springer Science & 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.

Endogenous steroids

Precursors

Corticosteroids

Glucocorticoids	3α,5α-Tetrahydrocorticosterone 5α-Dihydrocorticosterone 11-Deoxycorticosterone 11-Deoxycortisol 11-Ketoprogesterone 21-Deoxycortisol 21-Deoxycortisone Corticosterone Cortisol Cortisone 17α-Hydroxypregnenolone 17α-Hydroxyprogesterone Pregnenolone Progesterone Metabolites:5α-Dihydrocortisol 3α,5α-Tetrahydrocortisol
Mineralocorticoids	5α-Dihydroaldosterone 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone) 11-Deoxycortisol 11-Deoxycorticosterone 11β-Hydroxyprogesterone (21-deoxycorticosterone) 18-Hydroxy-11-deoxycorticosterone 18-Hydroxycorticosterone 18-Hydroxyprogesterone Aldosterone Corticosterone Cortisol

Sex steroids

Androgens	11-Ketodihydrotestosterone 11-Ketotestosterone 7β-Hydroxyepiandrosterone 11β-Hydroxyandrostenedione Adrenosterone (11-ketoandrostenedione) Androstenediol Androstenedione Androsterone Dehydroandrosterone DHEA DHEA sulfate Dihydrotestosterone Epiandrosterone Epitestosterone 16α-Hydroxyandrostenedione 16α-Hydroxy-DHEA 16α-Hydroxy-DHEA sulfate Testosterone Metabolites:3α-Androstanediol 3α-Androstanediol glucuronide 3β-Androstanediol 5β-Dihydrotestosterone 3α-Etiocholanediol 3β-Etiocholanediol Androstanetriols Androstenediol sulfate Androstenetriol Androsterone glucuronide Androsterone sulfate Dihydrotestosterone glucuronide Dihydrotestosterone sulfate Etiocholanedione Etiocholanolone Etiocholanolone glucuronide Epietiocholanolone Testosterone glucuronide Testosterone sulfate
Estrogens	Estranes:Estetrol Estradiol Estrone Estriol 17α-Estradiol 16β-Epiestriol (16β-hydroxyestradiol) 17α-Epiestriol (16α-hydroxy-17α-estradiol) 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 2-Hydroxyestradiol 2-Hydroxyestriol 2-Hydroxyestrone 4-Hydroxyestradiol 4-Hydroxyestriol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 16α-Hydroxyestrone 16β-Hydroxyestrone 16-Ketoestradiol 16-Ketoestrone Others:27-Hydroxycholesterol 3α-Androstanediol 3β-Androstanediol 4-Androstenedione 5-Androstenediol DHEA DHEA sulfate 7-Keto-DHEA 7α-Hydroxy-DHEA 16α-Hydroxy-DHEA Metabolites:2-Methoxyestradiol 2-Methoxyestrone 2-Methoxyestriol 4-Methoxyestriol Estradiol disulfate Estradiol glucuronide Estradiol 3-glucuronide Estradiol 3-glucuronide 17β-sulfate Estradiol sulfate Estradiol 17β-sulfate Estrone glucuronide Estrone sulfate Estriol glucuronide Estriol sulfate Lipoidal estradiol (e.g.,estradiol stearate,estradiol palmitate)
Progestogens	Progesterone 16α-Hydroxyprogesterone 17α-Hydroxyprogesterone 20α-Dihydroprogesterone 20β-Dihydroprogesterone 5α-Dihydroprogesterone 11-Deoxycorticosterone 5α-DHDOC Metabolites:Allopregnanediol Pregnanediol Pregnanediol glucuronide Pregnanetriol