Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-11-09 23:11:35 UTC |
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HMDB ID | HMDB0000015 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cortexolone |
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Description | Cortexolone, also known as cortodoxone or 11 deoxycortisol, 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. Thus, cortexolone is considered to be a steroid lipid molecule. Cortexolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Cortexolone is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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11-Desoxy-17-hydroxycorticosterone | ChEBI | Cortodoxone | ChEBI | Reichstein substance S | HMDB | Substance S, reichstein's | HMDB | 11 Deoxycortisol | HMDB | 11 Desoxycortisol | HMDB | 11 Desoxycortisone | HMDB | S, Reichstein's substance | HMDB | 11-Desoxycortisol | HMDB | 11-Desoxycortisone | HMDB | Reichsteins substance S | HMDB | 11-Deoxycortisol | HMDB | SK&F 3050 | HMDB | Reichstein's substance S | HMDB | 11-Deoxy-17-hydroxycorticosterone | HMDB | 11-Deoxyhydrocortisone | HMDB | 11-Desoxyhydrocortisone | HMDB | 17,21-Dihydroxy-4-pregnene-3,20-dione | HMDB | 17,21-Dihydroxypregn-4-ene-3,20-dione | HMDB | 17,21-Dihydroxyprogesterone | HMDB | 17-Hydroxy-11-deoxycorticosterone | HMDB | 17alpha-Hydroxycortexone | HMDB | 20-Dione 17,21-dihydroxypregn-4-ene-3 | HMDB | 4-Pregnene-17alpha,21-diol-3,20-dione | HMDB | Compound S | HMDB | 11-Deoxy-17-hydrocorticosterone | HMDB | 11-Deoxycortisone | HMDB | 11-Desoxy-17α-hydroxycorticosterone | HMDB | 11-Desoxy-17alpha-hydroxycorticosterone | HMDB | 17,21-Dihydroxypregn-4-en-3,20-dione | HMDB | 17Α,21-dihydroxy-4-pregnen-3,20-dione | HMDB | 17Α,21-dihydroxypregn-4-ene-3,20-dione | HMDB | 17Α,21-dihydroxyprogesterone | HMDB | 17Α-hydroxycortexone | HMDB | 4-Pregnen-17α,21-diol-3,20-dione | HMDB | 4-Pregnene-17α,21-diol-3,20-dione | HMDB | 17alpha,21-Dihydroxy-4-pregnen-3,20-dione | HMDB | 17alpha,21-Dihydroxypregn-4-ene-3,20-dione | HMDB | 17alpha,21-Dihydroxyprogesterone | HMDB | 4-Pregnen-17alpha,21-diol-3,20-dione | HMDB | Cortexolone | MeSH |
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Chemical Formula | C21H30O4 |
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Average Molecular Weight | 346.4605 |
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Monoisotopic Molecular Weight | 346.214409448 |
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IUPAC Name | (1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one |
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Traditional Name | (1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one |
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CAS Registry Number | 152-58-9 |
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SMILES | [H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C |
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InChI Identifier | InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1 |
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InChI Key | WHBHBVVOGNECLV-OBQKJFGGSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Hydroxysteroids |
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Direct Parent | 21-hydroxysteroids |
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Alternative Parents | |
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Substituents | - 21-hydroxysteroid
- Progestogin-skeleton
- Pregnane-skeleton
- 20-oxosteroid
- 3-oxo-delta-4-steroid
- 3-oxosteroid
- 17-hydroxysteroid
- Oxosteroid
- Delta-4-steroid
- Cyclohexenone
- Alpha-hydroxy ketone
- Tertiary alcohol
- Cyclic alcohol
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organooxygen compound
- Primary alcohol
- Carbonyl group
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | - glucocorticoid (CHEBI:28324 )
- deoxycortisol (CHEBI:28324 )
- Glucocorticoids (C05488 )
- C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C05488 )
- C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030086 )
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 215 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | 3.08 | SANGSTER (1994) |
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Predicted Properties | |
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General References | - Homma K, Hasegawa T, Masumoto M, Takeshita E, Watanabe K, Chiba H, Kurosawa T, Takahashi T, Matsuo N: Reference values for urinary steroids in Japanese newborn infants: gas chromatography/mass spectrometry in selected ion monitoring. Endocr J. 2003 Dec;50(6):783-92. [PubMed:14709852 ]
- Trakakis E, Laggas D, Salamalekis E, Creatsas G: 21-Hydroxylase deficiency: from molecular genetics to clinical presentation. J Endocrinol Invest. 2005 Feb;28(2):187-92. [PubMed:15887869 ]
- Krone N, Riepe FG, Gotze D, Korsch E, Rister M, Commentz J, Partsch CJ, Grotzinger J, Peter M, Sippell WG: Congenital adrenal hyperplasia due to 11-hydroxylase deficiency: functional characterization of two novel point mutations and a three-base pair deletion in the CYP11B1 gene. J Clin Endocrinol Metab. 2005 Jun;90(6):3724-30. Epub 2005 Mar 8. [PubMed:15755848 ]
- Adinoff B, Krebaum SR, Chandler PA, Ye W, Brown MB, Williams MJ: Dissection of hypothalamic-pituitary-adrenal axis pathology in 1-month-abstinent alcohol-dependent men, part 1: adrenocortical and pituitary glucocorticoid responsiveness. Alcohol Clin Exp Res. 2005 Apr;29(4):517-27. [PubMed:15834216 ]
- Brown JR, Cavanaugh AH, Farnsworth WE: A simple radioimmunoassay for plasma cortisol and 11-deoxycortisol (17, 21-dihydroxy-4-pregnene-3, 20-dione). Steroids. 1976 Oct;28(4):487-98. [PubMed:1034356 ]
- den Brinker M, Joosten KF, Liem O, de Jong FH, Hop WC, Hazelzet JA, van Dijk M, Hokken-Koelega AC: Adrenal insufficiency in meningococcal sepsis: bioavailable cortisol levels and impact of interleukin-6 levels and intubation with etomidate on adrenal function and mortality. J Clin Endocrinol Metab. 2005 Sep;90(9):5110-7. Epub 2005 Jun 28. [PubMed:15985474 ]
- Lee HH, Won GS, Chao HT, Lee YJ, Chung BC: Novel missense mutations, GCC [Ala306]- > GTC [Val] and ACG [Thr318]- > CCG [Pro], in the CYP11B1 gene cause steroid 11beta-hydroxylase deficiency in the Chinese. Clin Endocrinol (Oxf). 2005 Apr;62(4):418-22. [PubMed:15807871 ]
- Zachmann M, Tassinari D, Prader A: Clinical and biochemical variability of congenital adrenal hyperplasia due to 11 beta-hydroxylase deficiency. A study of 25 patients. J Clin Endocrinol Metab. 1983 Feb;56(2):222-9. [PubMed:6296182 ]
- White PC, Tusie-Luna MT, New MI, Speiser PW: Mutations in steroid 21-hydroxylase (CYP21). Hum Mutat. 1994;3(4):373-8. [PubMed:8081391 ]
- Bradshaw KD, Milewich L, Mason JI, Parker CR Jr, MacDonald PC, Carr BR: Steroid secretory characteristics of a virilizing adrenal adenoma in a woman. J Endocrinol. 1994 Feb;140(2):297-307. [PubMed:8169562 ]
- Bureik M, Bruck N, Hubel K, Bernhardt R: The human mineralocorticoid receptor only partially differentiates between different ligands after expression in fission yeast. FEMS Yeast Res. 2005 Apr;5(6-7):627-33. [PubMed:15780662 ]
- Dragan CA, Zearo S, Hannemann F, Bernhardt R, Bureik M: Efficient conversion of 11-deoxycortisol to cortisol (hydrocortisone) by recombinant fission yeast Schizosaccharomyces pombe. FEMS Yeast Res. 2005 Apr;5(6-7):621-5. [PubMed:15780661 ]
- Mellon SH, Miller WL: Extraadrenal steroid 21-hydroxylation is not mediated by P450c21. J Clin Invest. 1989 Nov;84(5):1497-502. [PubMed:2808702 ]
- Sakamoto N, Matsukura S, Tsuboi S, Tokumiya T, Imura H: Radioimmunoassay for 11-deoxycortisol using iodine-labeled tracer. Endocrinol Jpn. 1976 Aug;23(4):359-63. [PubMed:1024042 ]
- Tjeerdsma G, Sluiter WJ, Hew JM, Molenaar WM, de Lange WE, Dullaart RP: Hyperprolactinaemia is associated with a higher prevalence of pituitary-adrenal dysfunction in non-functioning pituitary macroadenoma. Eur J Endocrinol. 1996 Sep;135(3):299-308. [PubMed:8890720 ]
- Hughes IA, Arisaka O, Perry LA, Honour JW: Early diagnosis of 11 beta-hydroxylase deficiency in two siblings confirmed by analysis of a novel steroid metabolite in newborn urine. Acta Endocrinol (Copenh). 1986 Mar;111(3):349-54. [PubMed:3515819 ]
- Curnow KM, Tusie-Luna MT, Pascoe L, Natarajan R, Gu JL, Nadler JL, White PC: The product of the CYP11B2 gene is required for aldosterone biosynthesis in the human adrenal cortex. Mol Endocrinol. 1991 Oct;5(10):1513-22. [PubMed:1775135 ]
- White PC, Dupont J, New MI, Leiberman E, Hochberg Z, Rosler A: A mutation in CYP11B1 (Arg-448----His) associated with steroid 11 beta-hydroxylase deficiency in Jews of Moroccan origin. J Clin Invest. 1991 May;87(5):1664-7. [PubMed:2022736 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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