You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information |
---|
Version | 4.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2005-11-16 15:48:42 UTC |
---|
Update Date | 2020-10-09 20:59:04 UTC |
---|
HMDB ID | HMDB0000319 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | 18-Hydroxycorticosterone |
---|
Description | 18-Hydroxycorticosterone is a corticosteroid and a derivative of corticosterone. If it is present in sufficiently high concentrations, it can lead to serious electrolyte imbalances (an electrolyte toxin). 18-Hydroxycorticosterone serves as an intermediate in the synthesis of aldosterone by the enzyme aldosterone synthase in the zona glomerulosa. Chronically high levels of 18-hydroxycorticosterone are associated with at least three inborn errors of metabolism including adrenal hyperplasia type V, corticosterone methyl oxidase I deficiency, and corticosterone methyl oxidase II deficiency. Each of these conditions is characterized by excessive amounts of sodium being released in the urine (salt wasting), along with insufficient release of potassium in the urine, usually beginning in the first few weeks of life. This imbalance leads to low levels of sodium and high levels of potassium in the blood (hyponatremia and hyperkalemia, respectively). Individuals with corticosterone methyloxidase deficiency can also have high levels of acid in the blood (metabolic acidosis). Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). The hyponatremia, hyperkalemia, and metabolic acidosis associated with corticosterone methyloxidase deficiency can cause nausea, vomiting, dehydration, low blood pressure, extreme tiredness (fatigue), and muscle weakness. |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
11b,18,21-Trihydroxy-pregn-4-ene-3,20-dione | HMDB | 18 Hydrocorticosterone | HMDB | 18 Hydroxycorticosterone | HMDB | 18-Hydrocorticosterone | HMDB | Hydroxycorticosterone, 18 | HMDB | (11Β)-11,18,21-trihydroxypregn-4-ene-3,20-dione | HMDB | (11beta)-11,18,21-Trihydroxypregn-4-ene-3,20-dione | HMDB |
|
---|
Chemical Formula | C21H30O5 |
---|
Average Molecular Weight | 362.4599 |
---|
Monoisotopic Molecular Weight | 362.20932407 |
---|
IUPAC Name | (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 |
---|
Traditional Name | (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 |
---|
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 |
---|
Description | belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Steroids and steroid derivatives |
---|
Sub Class | Hydroxysteroids |
---|
Direct Parent | 21-hydroxysteroids |
---|
Alternative Parents | |
---|
Substituents | - Progestogin-skeleton
- 21-hydroxysteroid
- Pregnane-skeleton
- 20-oxosteroid
- 18-hydroxysteroid
- 3-oxo-delta-4-steroid
- 3-oxosteroid
- 11-hydroxysteroid
- 11-beta-hydroxysteroid
- Oxosteroid
- Delta-4-steroid
- Cyclohexenone
- Alpha-hydroxy ketone
- Cyclic alcohol
- Ketone
- Secondary alcohol
- Cyclic ketone
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Alcohol
- Organooxygen compound
- Primary alcohol
- Aliphatic homopolycyclic compound
|
---|
Molecular Framework | Aliphatic homopolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Health effect: |
---|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Industrial application: Biological role: |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
Spectra |
---|
| Spectrum Type | Description | Splash Key | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-1639000000-7012f18a6579e07dc571 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-03di-1410290000-5789e767e5a0058f10ed | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01r2-0019000000-8a12570d1c1a01069d09 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004j-0119000000-2b8864299061070cced5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0019-3494000000-ebcb1ff70c533c4c9459 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0009000000-0a027947a1d058fb84b7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03dl-1019000000-cb3605cb617647c036e0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05fr-5094000000-8d05b88622baf6731c7f | Spectrum |
|
---|
Biological Properties |
---|
Cellular Locations | |
---|
Biospecimen Locations | |
---|
Tissue Locations | |
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
Blood | Detected and Quantified | 0.000550-0.00138 uM | Children (1 - 13 years old) | Both | Normal | | details |
|
---|
Abnormal Concentrations |
---|
| |
Blood | Detected and Quantified | 0.030 (0.012-0.057) uM | Children (1-13 years old) | Both | Terminal aldosterone biosynthesis defects | | details |
|
---|
Associated Disorders and Diseases |
---|
Disease References | Terminal aldosterone biosynthesis defects |
---|
- Peter M, Partsch CJ, Sippell WG: Multisteroid analysis in children with terminal aldosterone biosynthesis defects. J Clin Endocrinol Metab. 1995 May;80(5):1622-7. [PubMed:7745009 ]
|
|
---|
Associated OMIM IDs | None |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB021945 |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | 10748 |
---|
KEGG Compound ID | C01124 |
---|
BioCyc ID | 18-HYDROXYCORTICOSTERONE |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | 18-Hydroxycorticosterone |
---|
METLIN ID | 5308 |
---|
PubChem Compound | 11222 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 16485 |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | MDB00000144 |
---|
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 ]
|
---|