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
CAS Number	561-65-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16485 ;
ChemSpider	10748 ;
ECHA InfoCard	100.008.384
MeSH	18-hydroxycorticosterone
PubChem CID	11222;
UNII	4U5T0O9SI3 ;
CompTox Dashboard (EPA)	DTXSID80897516 ;
	InChI 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 Key: HFSXHZZDNDGLQN-ZVIOFETBSA-N ; 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;
	SMILES 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
Chemical formula	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). verify (what is ?) 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^{[citation needed]}

18-Hydroxycorticosterone serves as an intermediate in the synthesis of aldosterone by the enzyme aldosterone synthase in the zona glomerulosa.^[6] It is also an intermediate in the biosynthesis of corticosterone. It spontaneously and reversibly converts to various less polar forms and derivatives, some of which serve as precursors to aldosterone or corticosterone. Specifically, 21-hydroxy-11,18-oxido-4-pregnene-3,20-dione (18-DAL) is hydroxylated to aldosterone in the presence of malate and NADP+ at pH 4.8, indicating that 18-DAL acts as a metabolic intermediate between 18-hydroxycorticosterone and aldosterone.^[7] Corticosterone is a mediate precursor in this biosynthesis pathway, with 18-hydroxycorticosterone serving as an intermediate between corticosterone and aldosterone.^[8]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ "Human Metabolome Database: Showing metabocard for 18-Hydroxycorticosterone (HMDB0000319)". Archived from the original on 2023-06-06. Retrieved 2024-04-06.
^ Marver D (1980). "Aldosterone action in target epithelia". Vitam Horm. Vitamins & Hormones. 38: 55–117. doi:10.1016/s0083-6729(08)60484-7. ISBN 978-0-12-709838-8. PMID 6182690.
^ Lantos CP, Damasco MC, Aragonés A, Ceballos NR, Burton G, Cozza EN (1987). "Versatile steroid molecules at the end of the aldosterone pathway". J Steroid Biochem. 27 (4–6): 791–800. doi:10.1016/0022-4731(87)90151-8. PMID 3320559.

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[pmid31296661-1] 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.

[pmid22238407-2] 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.

[pmid22145132-3] 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.

[pmid15356073-4] 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.

[pmid20960793-5] 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.

[6] "Human Metabolome Database: Showing metabocard for 18-Hydroxycorticosterone (HMDB0000319)". Archived from the original on 2023-06-06. Retrieved 2024-04-06.

[pmid6182690-7] Marver D (1980). "Aldosterone action in target epithelia". Vitam Horm. Vitamins & Hormones. 38: 55–117. doi:10.1016/s0083-6729(08)60484-7. ISBN 978-0-12-709838-8. PMID 6182690.

[pmid3320559-8] Lantos CP, Damasco MC, Aragonés A, Ceballos NR, Burton G, Cozza EN (1987). "Versatile steroid molecules at the end of the aldosterone pathway". J Steroid Biochem. 27 (4–6): 791–800. doi:10.1016/0022-4731(87)90151-8. PMID 3320559.

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Function

See also

References