Cortexolone
Cortexolone is also known as 11-Deoxy-17-hydroxy-corticosterone or 11-Deoxy-cortisol. Cortexolone is considered to be practically insoluble (in water) and relatively neutral. Cortexolone can be found throughout all human tissues; and in blood and urine. Cortexolone can be found throughout a human cell. Cortexolone is found in eukaryotic species, from E.coli to Humans.Cortexolone is the precursor of cortisol. Accumliation of Cortexolone can happen in a defect known as congenital adrenal hyperplasia, which is due to 11-beta-hydroxylase deficiency, resliting in androgen excess, virilization, and hypertension. (PMID:2022736 ) A 17-hydroxycorticosteroid with glucocorticoid and anti-inflammatory activities. (PubChem).
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB00015 (Cortexolone)
C21H30O4
346.4605
346.214409448
(2R,10R,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
(2R,10R,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
152-58-9
[H]C12CC[C@](O)(C(=O)CO)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
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
WHBHBVVOGNECLV-HMGFGKNBSA-N
Not classified
Detected and Quantified
Solid
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-002b-0039000000-87b1084eceb70df1b098View in MoNA
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0bvj-0297000000-3406beb1da4b4b19363fView in MoNA
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-00ku-0590000000-5abafee5940d11aa42ecView in MoNA
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-0002-0019000000-d2a530dacb3a06454bc7View in MoNA
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-000i-3098000000-41ab989c032a52f9b68dView in MoNA
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0a4i-6091000000-135d326dc71c0a21798aView in MoNA
Not Available
None
None
Not Available
Not Available
Not Available
Not Available
FDB021872
Not Available
Not Available
C05488
11-DEOXY-CORTISOL
45914
Cortexolone
HMDB00015
HMDB00015
5088
53477676
Not Available
Not Available
- 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 ]
- White PC, Tusie-Luna MT, New MI, Speiser PW: Mutations in steroid 21-hydroxylase (CYP21). Hum Mutat. 1994;3(4):373-8. [PubMed:8081391 ]
- 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 ]
- Mellon SH, Miller WL: Extraadrenal steroid 21-hydroxylation is not mediated by P450c21. J Clin Invest. 1989 Nov;84(5):1497-502. [PubMed:2808702 ]
- 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 ]
- 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 ]
- 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 ]
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
Reactions
References
- 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 ]
- General function:
- Involved in sequence-specific DNA binding transcription factor activity
- Specific function:
- Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels
- Gene Name:
- NR3C2
- Uniprot ID:
- P08235
- Molecular weight:
- 107066.6
- General function:
- Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
- Specific function:
- 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
- Gene Name:
- HSD3B1
- Uniprot ID:
- P14060
- Molecular weight:
- 42251.25
Reactions
- General function:
- Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
- Specific function:
- 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
- Gene Name:
- HSD3B2
- Uniprot ID:
- P26439
- Molecular weight:
- 42051.845
Reactions
- 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
- General function:
- Involved in monooxygenase activity
- Specific function:
- Not Available
- Gene Name:
- P450-CYP21B
- Uniprot ID:
- Q16874
- Molecular weight:
- 56000.9
- General function:
- Involved in monooxygenase activity
- Specific function:
- Not Available
- Gene Name:
- CYP21A2
- Uniprot ID:
- Q08AG9
- Molecular weight:
- 55972.9
- General function:
- Not Available
- Specific function:
- Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
- Gene Name:
- CYP21A2
- Uniprot ID:
- P08686
- Molecular weight:
- 56000.94