18-hydroxycorticosterone

Also known as 11b,18,21-Trihydroxy-pregn-4-ene-3,20-dione, (1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

18-Hydroxycorticosterone is an endogenous steroid. It is a derivative of corticosterone.

In the Vinony graph

Within Vinony's link graph, 18-hydroxycorticosterone is referenced by 167 other articles, and connects out to mometasone furoate, fludrocortisone and International Standard Book Number.

Vinony files it under Chembox image size set, Corticosteroids and ECHA InfoCard ID from Wikidata.

Its subject is documented across 7 Wikipedia language editions.

Chemical data

Formula: C21H30O5
Molecular weight: 362.5 g/mol
IUPAC name: (8S,9S,10R,11S,13R,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-13-(hydroxymethyl)-10-methyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@H]4C(=O)CO)CO)O
InChIKey: HFSXHZZDNDGLQN-ZVIOFETBSA-N
XLogP: 0.7
Polar surface area: 94.8 Å²
H-bond donors: 3
H-bond acceptors: 5
Formal charge: 0

via PubChem

Research

536 papers

[18-Hydroxycorticosterone (18-OH-B)].Nihon rinsho. Japanese journal of clinical medicine · 1995
[18-hydroxycorticosterone (18-OH-B)].Nihon rinsho. Japanese journal of clinical medicine · 1999
[18-hydroxycorticosterone (18-OH -B)].Nihon rinsho. Japanese journal of clinical medicine · 2005
[18-Hydroxycorticosterone, 18-hydroxydesoxycorticosterone. Why, when, how to determine plasma levels in some adrenal pathologies].Annales d'endocrinologie · 1990
[18-Hydroxycorticosterone (18-OH-B)].Nihon rinsho. Japanese journal of clinical medicine · 2010

via PubMed

Wikidata facts

Subclass of: steroid
Mass: 362.209324

Show 6 more facts

Commons category: 18-Hydroxycorticosterone
subject has role: primary metabolite
found in taxon: Homo sapiens
chemical formula: C₂₁H₃₀O₅
isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@H]4C(=O)CO)CO)O
canonical SMILES: CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4C(=O)CO)CO)O

Sources (4)

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Encyclopedic overview

3 sections

Contents

Function
See also
References

18-Hydroxycorticosterone is an endogenous steroid. It is a derivative of corticosterone.

==Function== thumb|left|560px|Corticosteroid biosynthetic pathway in rat18-Hydroxycorticosterone serves as an intermediate in the synthesis of aldosterone by the enzyme aldosterone synthase in the zona glomerulosa. 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. Corticosterone is a mediate precursor in this biosynthesis pathway, with 18-hydroxycorticosterone serving as an intermediate between corticosterone and aldosterone.

Excerpted from Wikipedia’s “18-hydroxycorticosterone” article, available under the CC BY-SA 4.0 licence.