| Common Name |
18-Hydroxycorticosterone
| Description |
11 beta,18,21-Trihydroxypregn-4-ene-3,20-dione. 18-Hydroxycorticosterone is a derivative of corticosterone. It serves as an intermediate in the synthesis of aldosterone by the enzyme aldosterone synthase in the zona glomerliosa.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
11b,18,21-Trihydroxy-pregn-4-ene-3,20-dioneHMDB
18 HydrocorticosteroneMeSH
18 HydroxycorticosteroneMeSH
18-HydrocorticosteroneMeSH
Hydroxycorticosterone, 18MeSH
| Chemical Formlia |
C21H30O5
| Average Molecliar Weight |
362.4599
| Monoisotopic Molecliar Weight |
362.20932407
| IUPAC Name |
(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
| Traditional Name |
18 hydroxycorticosterone
| CAS Registry Number |
561-65-9
| SMILES |
[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(CO)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
| InChI Identifier |
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
| InChI Key |
HFSXHZZDNDGLQN-ZVIOFETBSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Component of C21-Steroid hormone metabolism
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.15 mg/mLALOGPS
logP1.28ALOGPS
logP0.74ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.8ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.77 m3·mol-1ChemAxon
Polarizability39.46 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Blood
| Tissue Location |
Adrenal Gland
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
11-beta-hydroxylase deficiency (CYP11B1)SMP00575Not Available
17-alpha-hydroxylase deficiency (CYP17)SMP00566Not Available
21-hydroxylase deficiency (CYP21)SMP00576Not Available
3-Beta-Hydroxysteroid Dehydrogenase DeficiencySMP00718Not Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencySMP00373Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase DeficiencySMP00372Not Available
Apparent mineralocorticoid excess syndromeSMP00717Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHSMP00371Not Available
Corticosterone methyl oxidase I deficiency (CMO I)SMP00577Not Available
Corticosterone methyl oxidase II deficiency – CMO IISMP00578Not Available
SteroidogenesisSMP00130map00140
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified0.030 (0.012-0.057) uMChildren (1-13 years old)BothTerminal aldosterone biosynthesis defects
7745009
details
| Associated Disorders and Diseases |
| Disease References |
| Aldosterone biosynthesis defects |
- Peter M, Partsch CJ, Sippell WG: Mlitisteroid analysis in children with terminal aldosterone biosynthesis defects. J Clin Endocrinol Metab. 1995 May;80(5):1622-7. [PubMed:7745009 ]
| Associated OMIM IDs |
610600 (Aldosterone biosynthesis defects)
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB021945
| KNApSAcK ID |
Not Available
| Chemspider ID |
10748
| KEGG Compound ID |
C01124
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
18-Hydroxycorticosterone
| NuGOwiki Link |
HMDB00319
| Metagene Link |
HMDB00319
| METLIN ID |
5308
| PubChem Compound |
11222
| PDB ID |
Not Available
| ChEBI ID |
16485
Product: 4E2RCat
References |
| Synthesis Reference |
Boudi, Ahmed; Lemoine, Pascale; Viossat, Bernard; Tomas, Alain; Fiet, Jean; Galons, Herve. A convenient synthesis of 18-hydroxycorticosterone and 18-hydroxy-11-desoxycorticosterone via stereospecific hypoiodination of 20-hydroxysteroids. Tetrahedron (1999), 55(16), 5171-5176. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Sonino N, Chow D, Levine LS, New MI: Clinical response to metyrapone as indicated by measurement of mineralocorticoids and glucocorticoids in normal children. Clin Endocrinol (Oxf). 1981 Jan;14(1):31-9. [PubMed:7226574 ]
- Vecsei P, Abdelhamid S, Mittelstadt GV, Lichtwald K, Haack D, Lewicka S: Aldosterone metabolites and possible aldosterone precursors in hypertension. J Steroid Biochem. 1983 Jul;19(1A):345-51. [PubMed:6887870 ]
- Kooner JS, Few JD, Lee CY, Taylor GM, James VH: Investigation of the salivary 18-hydroxycorticosterone:aldosterone ratio in man using a direct assay. J Steroid Biochem Mol Biol. 1991 Mar;38(3):377-82. [PubMed:2009228 ]
- Gomez-Sanchez CE, Clore JN, Estep HL, Watlington CO: Effect of chronic adrenocorticotropin stimulation on the excretion of 18-hydroxycortisol and 18-oxocortisol. J Clin Endocrinol Metab. 1988 Aug;67(2):322-6. [PubMed:2839536 ]
- Honda M, Tsuchiya M, Tamura H, Watanabe H, Izumi Y, Hatano M, Shiratsuchi T, Den K, Kawaoi A, Okano T: In vivo and in vitro studies on steroid metabolism in a case of primary aldosteronism with multiple lesions of adenoma and nodular hyperplasia. Endocrinol Jpn. 1982 Oct;29(5):529-40. [PubMed:6303762 ]
- Vecsei P, Benraad TJ, Hofman J, Abdelhamid S, Haack D, Lichtwald K: Direct radioimmunoassays for “aldosterone” and “18-hydroxycorticosterone” in unprocessed urine, and their use in screening to distinguish primary aldosteronism from hypertension. Clin Chem. 1982 Mar;28(3):453-6. [PubMed:7067086 ]
|
Enzymes
- General function:
- Involved in monooxygenase activity
- Specific function:
- Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
- Gene Name:
- CYP11B1
- Uniprot ID:
- P15538
- Molecular weight:
- 57572.44
- General function:
- Involved in monooxygenase activity
- Specific function:
- Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
- Gene Name:
- CYP11B2
- Uniprot ID:
- P19099
- Molecular weight:
- 57559.62
Reactions
| Corticosterone + reduced adrenal ferredoxin + Oxygen → 18-Hydroxycorticosterone + oxidized adrenal ferredoxin + Water |
details |
| Corticosterone + Reduced adrenal ferredoxin + Oxygen → 18-Hydroxycorticosterone + Oxidized adrenal ferredoxin + Water |
details |
| 18-Hydroxycorticosterone + Reduced adrenal ferredoxin + Oxygen → Aldosterone + Oxidized adrenal ferredoxin + Water |
details |
PMID: 9399643