18-Hydroxycorticosterone

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

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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16485 Y
ChemSpider	10748 Y
ECHA InfoCard	100.008.384
MeSH	18-hydroxycorticosterone
PubChem CID	11222
UNII	4U5T0O9SI3 Y
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 Y Key: HFSXHZZDNDGLQN-ZVIOFETBSA-N Y 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). N verify (what is YN ?) Infobox references

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]

See also

• 18-Hydroxycortisol
• Aldosterone synthase