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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 15:12:11 UTC |
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Update Date | 2020-11-09 23:17:05 UTC |
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HMDB ID | HMDB0002802 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cortisone |
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Description | Cortisone is a naturally occurring glucocorticoid. It has been used in replacement therapy for adrenal insufficiency and as an anti-inflammatory agent. Cortisone itself is inactive. It is converted in the liver into the active metabolite cortisol (Martindale, The Extra Pharmacopoeia, 30th ed, p726). Cortisone is a corticosteroid hormone released by the adrenal gland in response to stress. One of cortisone's effects on the body, and a potentially harmful side effect when administered clinically, is the suppression of the immune system. This is an explanation for the apparent correlation between high stress and sickness (Wikipedia ). |
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Structure | |
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Synonyms | Value | Source |
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11-Dehydro-17-hydroxycorticosterone | ChEBI | 17-Hydroxy-11-dehydrocorticosterone | ChEBI | 17alpha,21-Dihydroxy-4-pregnene-3,11,20-trione | ChEBI | 4-Pregnene-17alpha,21-diol-3,11,20-trione | ChEBI | Cortison | ChEBI | Delta(4)-Pregnene-17alpha,21-diol-3,11,20-trione | ChEBI | Kendall's compound e | ChEBI | Kortison | ChEBI | Pregn-4-en-17alpha,21-diol-3,11,20-trione | ChEBI | Reichstein's substance fa | ChEBI | Wintersteiner's compound F | ChEBI | 17a,21-Dihydroxy-4-pregnene-3,11,20-trione | Generator | 17Α,21-dihydroxy-4-pregnene-3,11,20-trione | Generator | 4-Pregnene-17a,21-diol-3,11,20-trione | Generator | 4-Pregnene-17α,21-diol-3,11,20-trione | Generator | delta(4)-Pregnene-17a,21-diol-3,11,20-trione | Generator | Δ(4)-pregnene-17α,21-diol-3,11,20-trione | Generator | Pregn-4-en-17a,21-diol-3,11,20-trione | Generator | Pregn-4-en-17α,21-diol-3,11,20-trione | Generator | Δ(4)-pregnene-17a,21-diol-3,11,20-trione | HMDB | Andreson | HMDB | Anusol HC | HMDB | Balneol-HC | HMDB | beta-HC | HMDB | Colocort | HMDB | Compound e | HMDB | Corlin | HMDB | Cortadren | HMDB | Cortandren | HMDB | Cortef | HMDB | Cortef acetate | HMDB | Cortisal | HMDB | Cortisate | HMDB | Cortisone acetate | HMDB | Cortistal | HMDB | Cortivite | HMDB | Cortogen | HMDB | Cortone | HMDB | Cortril | HMDB | Dermacort | HMDB | Dricort | HMDB | Flexicort | HMDB | Florinef | HMDB | Fludrocortisone acetate | HMDB | Glycort | HMDB | Hemsol-HC | HMDB | Hi-cor | HMDB | Incortin | HMDB | Kendall'S compound | HMDB | Locoid | HMDB | Locoid lipocream | HMDB | Micort-HC | HMDB | Nogenic HC | HMDB | Orabase hca | HMDB | Pandel | HMDB | Prestwick_132 | HMDB | Reichstein fa | HMDB | Scheroson | HMDB | Solu-cortef | HMDB | Stie-cort | HMDB | Texacort | HMDB | Westcort | HMDB | Adreson | HMDB | Cortone acetate | MeSH | 17-Hydroxy-3,11,20-trioxopregn-4-en-21-yl acetate | MeSH |
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Chemical Formula | C21H28O5 |
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Average Molecular Weight | 360.444 |
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Monoisotopic Molecular Weight | 360.193674006 |
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IUPAC Name | (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione |
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Traditional Name | (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione |
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CAS Registry Number | 53-06-5 |
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SMILES | [H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C |
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InChI Identifier | InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1 |
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InChI Key | MFYSYFVPBJMHGN-ZPOLXVRWSA-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 | - Progestogin-skeleton
- 21-hydroxysteroid
- Pregnane-skeleton
- 20-oxosteroid
- 3-oxo-delta-4-steroid
- 3-oxosteroid
- 17-hydroxysteroid
- Oxosteroid
- 11-oxosteroid
- Delta-4-steroid
- Cyclohexenone
- Alpha-hydroxy ketone
- Cyclic alcohol
- Tertiary alcohol
- Cyclic ketone
- Ketone
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Primary alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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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 | 222 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.28 mg/mL at 25 °C | Not Available | LogP | 1.47 | HANSCH,C ET AL. (1995) |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00kf-2910000000-da435cee921dd7b9f8e6 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00kf-2910000000-da435cee921dd7b9f8e6 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-05ai-5879000000-d8ce750671bf51b487e2 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0f79-2918800000-ab308a6a5023c34bc22f | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-03di-0009000000-5d34de066e82cc9f0a41 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-03di-0900000000-24ec04976da03c3f9c77 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0fdo-4900000000-d0880bfc6f3d80e4aa72 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-03di-3940000000-16be8720b1c49cea9b06 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-004i-0009000000-6c22c083c2dfab97a299 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-004i-0109000000-48c96b3d1471c5cd6171 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-002r-0914000000-2466a9146383b4265e42 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-000i-0900000000-214430a00501054cc774 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-059j-1900000000-0e23516e07f0baf74c79 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0abj-1900000000-ad0282ab7188d9ec3dc1 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0aba-3900000000-e36e464b157b3e6159f1 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0a4j-5900000000-fe9092d76099e1e70a4e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0aou-6900000000-1b218b97a890ac7e8f45 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-03fr-0049000000-3bd424d473bdadd2b9b4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-03di-0039000000-fd181dfb87e1cbb8ab6f | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-03di-0049000000-7633496a1a53bda21707 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-004i-0009000000-59db5e627634e4be3907 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-004i-0009000000-9781e204df305d722d2d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-004i-0009000000-0b5e40226163a1a334db | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03dl-0009000000-946472abc72d41b1633c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-003u-0149000000-efb3f94efcbdfc468859 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a5j-2392000000-d014016e46f2ae8b1bd1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0009000000-1c4a8c3698ff1bfa2bd9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0pb9-2029000000-82b546174619108311f8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ab9-8093000000-47f7996c84edb1324aad | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane
- Endoplasmic reticulum
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Biospecimen Locations | |
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Tissue Locations | - Adipose Tissue
- Adrenal Cortex
- Adrenal Gland
- Epidermis
- Fibroblasts
- Intestine
- Kidney
- Neuron
- Placenta
- Skeletal Muscle
- Testis
- Thyroid Gland
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.0411 (0.0222 - 0.0750) uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.0380 (0.0222 - 0.0750) uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.0624 +/- 0.009 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.011 +/- 0.001 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | ovarian cancer | | details | Blood | Detected and Quantified | 0.0466 +/- 0.0071 uM | Adult (>18 years old) | Both | Depersonalization syndrome | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Tooth Decay | | details | Urine | Detected and Quantified | 0.0042 +/- 0.0011 umol/mmol creatinine | Adult (>18 years old) | Both | Systemic lupus erythematosus (SLE) | | details | Urine | Detected and Quantified | 0.014 +/- 0.0013 umol/mmol creatinine | Adult (>18 years old) | Both | Systemic lupus erythematosus (SLE) | | details | Urine | Detected and Quantified | 0.0039 +/- 0.0012 umol/mmol creatinine | Adult (>18 years old) | Both | Rheumatoid arthritis | | details | Urine | Detected and Quantified | 0.0070 +/- 0.0014 umol/mmol creatinine | Adult (>18 years old) | Both | Rheumatoid arthritis | | details |
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Associated Disorders and Diseases |
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Disease References | Depersonalization disorder |
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- Nuller YL, Morozova MG, Kushnir ON, Hamper N: Effect of naloxone therapy on depersonalization: a pilot study. J Psychopharmacol. 2001 Jun;15(2):93-5. [PubMed:11448093 ]
| Ovarian cancer |
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- Gaul DA, Mezencev R, Long TQ, Jones CM, Benigno BB, Gray A, Fernandez FM, McDonald JF: Highly-accurate metabolomic detection of early-stage ovarian cancer. Sci Rep. 2015 Nov 17;5:16351. doi: 10.1038/srep16351. [PubMed:26573008 ]
| Tooth Decay |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Rheumatoid arthritis |
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- Straub RH, Weidler C, Demmel B, Herrmann M, Kees F, Schmidt M, Scholmerich J, Schedel J: Renal clearance and daily excretion of cortisol and adrenal androgens in patients with rheumatoid arthritis and systemic lupus erythematosus. Ann Rheum Dis. 2004 Aug;63(8):961-8. [PubMed:15249323 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023065 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 193441 |
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KEGG Compound ID | C00762 |
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BioCyc ID | CORTISONE |
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BiGG ID | 35911 |
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Wikipedia Link | Cortisone |
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METLIN ID | 271 |
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PubChem Compound | 222786 |
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PDB ID | Not Available |
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ChEBI ID | 16962 |
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Food Biomarker Ontology | Not Available |
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VMH ID | CORTSN |
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MarkerDB ID | MDB00030004 |
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References |
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Synthesis Reference | Ganis, Frank M.; Axelrod, Leonard R.; Miller, Leon L. The metabolism of hydrocortisone by kidney tissue in vitro. Journal of Biological Chemistry (1956), 218 841-8. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Zuber M, Miesel R, Brandl B: A patient with a high titer of antinuclear antibody and a functioning adrenal tumour. Clin Rheumatol. 1995 Jan;14(1):100-3. [PubMed:7743733 ]
- Edwin B, Raeder I, Trondsen E, Kaaresen R, Buanes T: Outpatient laparoscopic adrenalectomy in patients with Conn's syndrome. Surg Endosc. 2001 Jun;15(6):589-91. Epub 2001 Mar 13. [PubMed:11591947 ]
- Onyimba CU, Vijapurapu N, Curnow SJ, Khosla P, Stewart PM, Murray PI, Walker EA, Rauz S: Characterisation of the prereceptor regulation of glucocorticoids in the anterior segment of the rabbit eye. J Endocrinol. 2006 Aug;190(2):483-93. [PubMed:16899581 ]
- Weigand A, Hinzpeter B, Schicha H: [Deterioration of endocrine ophthalmology after radioiodine therapy in Graves' disease?]. Nuklearmedizin. 1998;37(7):234-8. [PubMed:9830613 ]
- Mark PJ, Waddell BJ: P-glycoprotein restricts access of cortisol and dexamethasone to the glucocorticoid receptor in placental BeWo cells. Endocrinology. 2006 Nov;147(11):5147-52. Epub 2006 Jul 27. [PubMed:16873536 ]
- Sandeep TC, Andrew R, Homer NZ, Andrews RC, Smith K, Walker BR: Increased in vivo regeneration of cortisol in adipose tissue in human obesity and effects of the 11beta-hydroxysteroid dehydrogenase type 1 inhibitor carbenoxolone. Diabetes. 2005 Mar;54(3):872-9. [PubMed:15734867 ]
- Pepe GJ, Albrecht ED: Regulation of the primate fetal adrenal cortex. Endocr Rev. 1990 Feb;11(1):151-76. [PubMed:2180686 ]
- Boman HG: Innate immunity and the normal microflora. Immunol Rev. 2000 Feb;173:5-16. [PubMed:10719663 ]
- Andrew R, Westerbacka J, Wahren J, Yki-Jarvinen H, Walker BR: The contribution of visceral adipose tissue to splanchnic cortisol production in healthy humans. Diabetes. 2005 May;54(5):1364-70. [PubMed:15855321 ]
- Sharma KK, Lindqvist A, Zhou XJ, Auchus RJ, Penning TM, Andersson S: Deoxycorticosterone inactivation by AKR1C3 in human mineralocorticoid target tissues. Mol Cell Endocrinol. 2006 Mar 27;248(1-2):79-86. Epub 2005 Dec 5. [PubMed:16337083 ]
- Draper N, Stewart PM: 11beta-hydroxysteroid dehydrogenase and the pre-receptor regulation of corticosteroid hormone action. J Endocrinol. 2005 Aug;186(2):251-71. [PubMed:16079253 ]
- AvRuskin TW, Krishnan N, Juan CS: Congenital adrenal hypoplasia and male pseudohermaphroditism due to DAX1 mutation, SF1 mutation or neither: a patient report. J Pediatr Endocrinol Metab. 2004 Aug;17(8):1125-32. [PubMed:15379426 ]
- Ferrari P, Bianchetti M, Frey FJ: Juvenile hypertension, the role of genetically altered steroid metabolism. Horm Res. 2001;55(5):213-23. [PubMed:11740142 ]
- Stormer FC, Reistad R, Alexander J: Glycyrrhizic acid in liquorice--evaluation of health hazard. Food Chem Toxicol. 1993 Apr;31(4):303-12. [PubMed:8386690 ]
- Bolt RJ, Van Weissenbruch MM, Popp-Snijders C, Sweep FG, Lafeber HN, Delemarre-van de Waal HA: Maturity of the adrenal cortex in very preterm infants is related to gestational age. Pediatr Res. 2002 Sep;52(3):405-10. [PubMed:12193676 ]
- Jiang JQ, Wang DS, Senthilkumaran B, Kobayashi T, Kobayashi HK, Yamaguchi A, Ge W, Young G, Nagahama Y: Isolation, characterization and expression of 11beta-hydroxysteroid dehydrogenase type 2 cDNAs from the testes of Japanese eel (Anguilla japonica) and Nile tilapia (Oreochromis niloticus). J Mol Endocrinol. 2003 Oct;31(2):305-15. [PubMed:14519098 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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