18-Hydroxycorticosterone
18-Hydroxycorticosterone
Names
IUPAC name
11β,18,21-Trihydroxypregn-4-ene-3,20-dione
Systematic IUPAC name
(1S,3aS,3bS,9aR,9bS,10S,11aR)-10-Hydroxy-1-(hydroxyacetyl)-11a-(hydroxymethyl)-9a-methyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.384
MeSH 18-hydroxycorticosterone
UNII
  • InChI=1S/C21H30O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,14-17,19,22-23,25H,2-7,9-11H2,1H3/t14-,15-,16+,17-,19+,20-,21+/m0/s1 checkY
    Key: HFSXHZZDNDGLQN-ZVIOFETBSA-N checkY
  • InChI=1/C21H30O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,14-17,19,22-23,25H,2-7,9-11H2,1H3/t14-,15-,16+,17-,19+,20-,21+/m0/s1
    Key: HFSXHZZDNDGLQN-ZVIOFETBBO
  • O=C4\C=C2/[C@]([C@H]1[C@@H](O)C[C@@]3([C@@H](C(=O)CO)CC[C@H]3[C@@H]1CC2)CO)(C)CC4
Properties
C21H30O5
Molar mass 362.46 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

18-Hydroxycorticosterone is an endogenous steroid.[1][2] It is a derivative of corticosterone.[3][4][5]

Function

Corticosteroid biosynthetic pathway in rat

18-Hydroxycorticosterone serves as an intermediate in the synthesis of aldosterone by the enzyme aldosterone synthase in the zona glomerulosa.

See also

References

  1. ↑ Reddish MJ, Guengerich FP (August 2019). "Human cytochrome P450 11B2 produces aldosterone by a processive mechanism due to the lactol form of the intermediate 18-hydroxycorticosterone". The Journal of Biological Chemistry. 294 (35): 12975–12991. doi:10.1074/jbc.RA119.009830. PMC 6721951. PMID 31296661.
  2. ↑ Mulatero P, di Cella SM, Monticone S, Schiavone D, Manzo M, Mengozzi G, Rabbia F, Terzolo M, Gomez-Sanchez EP, Gomez-Sanchez CE, Veglio F (March 2012). "18-hydroxycorticosterone, 18-hydroxycortisol, and 18-oxocortisol in the diagnosis of primary aldosteronism and its subtypes". The Journal of Clinical Endocrinology and Metabolism. 97 (3): 881–9. doi:10.1210/jc.2011-2384. PMID 22238407.
  3. ↑ Gupta V (October 2011). "Mineralocorticoid hypertension". Indian Journal of Endocrinology and Metabolism. 15 Suppl 4 (8): S298–312. doi:10.4103/2230-8210.86972. PMC 3230101. PMID 22145132.
  4. ↑ Freel EM, Shakerdi LA, Friel EC, Wallace AM, Davies E, Fraser R, Connell JM (September 2004). "Studies on the origin of circulating 18-hydroxycortisol and 18-oxocortisol in normal human subjects". The Journal of Clinical Endocrinology and Metabolism. 89 (9): 4628–33. doi:10.1210/jc.2004-0379. PMC 1283128. PMID 15356073.
  5. ↑ Izumi Y (July 2010). "[18-Hydroxycorticosterone (18-OH-B)]". Nihon Rinsho. Japanese Journal of Clinical Medicine (in Japanese). 68 (Suppl 7): 348–53. PMID 20960793.



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