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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 | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:22:44 UTC |
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HMDB ID | HMDB0000903 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Tetrahydrocortisone |
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Description | Cortisol is a corticosteroid hormone that is involved in the response to stress; it increases blood pressure and blood sugar levels and suppresses the immune system. Synthetic cortisol, also known as hydrocortisone, is used as a drug mainly to fight allergies and inflammation. -- Wikipedia ; As an oral or injectable drug, cortisol is also known as hydrocortisone. It is used as an immunosuppressive drug, given by injection in the treatment of severe allergic reactions such as anaphylaxis and angioedema, in place of prednisolone in patients who need steroid treatment but cannot take oral medication, and peri-operatively in patients on long-term steroid treatment to prevent an Addisonian crisis. -- Wikipedia . |
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Structure | |
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Synonyms | Value | Source |
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(3a,5b)-3,17,21-Trihydroxy-pregnane-11,20-dione | HMDB | 3,17-Dihydroxy-17-hydroxyacetyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-one | HMDB | 3a,17,21-Trihydroxy-5a-pregnane-11,20-dione | HMDB | 3a,17,21-Trihydroxy-5b-pregnane-11,20-dione | HMDB | 3alpha,17,21-Trihydroxy-5beta-pregnane-11,20-dione | HMDB | 3alpha,17,21-Trihydroxypregnane-11,20-dione | HMDB | 3b,17,21-Trihydroxy-5a-pregnane-11,20-dione | HMDB | 5a-Pregnan-3b,17a,21-triol-11,20-dion | HMDB | Ba 2681 | HMDB | Tetrahydro e | HMDB | Tetrahydro-cortisone | HMDB | Tetrahydrocompound e | HMDB | Tetrahydrocortison | HMDB | Urocortisone | HMDB |
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Chemical Formula | C21H32O5 |
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Average Molecular Weight | 364.4758 |
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Monoisotopic Molecular Weight | 364.224974134 |
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IUPAC Name | (1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one |
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Traditional Name | (1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one |
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CAS Registry Number | 53-05-4 |
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SMILES | [H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C |
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InChI Identifier | InChI=1S/C21H32O5/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/h12-15,18,22-23,26H,3-11H2,1-2H3/t12-,13-,14-,15-,18+,19-,20-,21-/m0/s1 |
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InChI Key | SYGWGHVTLUBCEM-SDYDLROXSA-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
- 20-oxosteroid
- Pregnane-skeleton
- 3-hydroxysteroid
- 11-oxosteroid
- Oxosteroid
- 3-beta-hydroxysteroid
- 17-hydroxysteroid
- Cyclic alcohol
- Tertiary alcohol
- Alpha-hydroxy ketone
- Ketone
- Secondary alcohol
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Primary alcohol
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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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 | 190 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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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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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0bua-3329000000-2fc8cde1a6f7cbf833e0 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-014i-1402490000-42e5bdb758e6ab7df7db | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-002b-0019000000-d250ba5babf82eddad0e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-002b-1960000000-f9b927b045d86760eeb6 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0a4l-4900000000-2464c3721a88f6a054fc | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kb-0009000000-9c872091c11d421f014c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00p1-0049000000-af1ad9a1ea8db1d650d4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052s-1192000000-21755048697813c79a2b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0009000000-784e6ec242f4642ea5b8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0bta-2029000000-9f2c95a66681e65408bb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9076000000-8477ed7e9c8d0c2c4587 | 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 | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.40 +/- 0.44 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 0.41 (0.38-0.49) umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 0.32 +/- 0.37 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 0.51 +/- 0.067 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.023 +/- 0.009 uM | Adult (>18 years old) | Both | Anorexia nervosa | | details | Urine | Detected and Quantified | 0.40 +/- 0.052 umol/mmol creatinine | Adult (>18 years old) | Female | Eating disorder | | details | Urine | Detected and Quantified | 1.5 +/- 0.53 umol/mmol creatinine | Adult (>18 years old) | Female | Eating disorder | | details |
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Associated Disorders and Diseases |
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Disease References | Anorexia nervosa |
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- Vierhapper H, Kiss A, Nowotny P, Wiesnagrotzki S, Monder C, Waldhausl W: Metabolism of cortisol in anorexia nervosa. Acta Endocrinol (Copenh). 1990 Jun;122(6):753-8. [PubMed:2165347 ]
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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 | FDB022310 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 16735652 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Tetrahydrocortisone |
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METLIN ID | 1915 |
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PubChem Compound | 12444617 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Baggett, Billy; Kinsella, Ralph A., Jr.; Doisy, Edward A. Hydrolysis of conjugates of urinary corticoids with b-glucuronidase. II. The isolation and determination of tetrahydrocortisone. Journal of Biological Chemistry (1953), 203 1013-22. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Mune T, White PC: Apparent mineralocorticoid excess: genotype is correlated with biochemical phenotype. Hypertension. 1996 Jun;27(6):1193-9. [PubMed:8641723 ]
- Weykamp CW, Penders TJ, Schmidt NA, Borburgh AJ, van de Calseyde JF, Wolthers BJ: Steroid profile for urine: reference values. Clin Chem. 1989 Dec;35(12):2281-4. [PubMed:2591044 ]
- Koren W, Grienspuhn A, Kuznetsov SR, Berezin M, Rosenthal T, Postnov YV: Enhanced Na+/H+ exchange in Cushing's syndrome reflects functional hypermineralocorticoidism. J Hypertens. 1998 Aug;16(8):1187-91. [PubMed:9794723 ]
- Rosler A, Leiberman E, Rosenmann A, Ben-Uzilio R, Weidenfeld J: Prenatal diagnosis of 11beta-hydroxylase deficiency congenital adrenal hyperplasia. J Clin Endocrinol Metab. 1979 Oct;49(4):546-51. [PubMed:314453 ]
- Stiefel P, Garcia-Morillo JS, Jimenez L, Pamies E, Miranda ML, Carneado J, Villar J, Leal-Cerro A: Role of ketoconazole treatment in urinary-free cortisol-to-cortisone and tetrahydrocortisol-to-tetrahydrocortisone ratios in nonectopic Cushing's syndrome. Endocrine. 2002 Aug;18(3):279-84. [PubMed:12450320 ]
- Wallace AM, Banfield E, Ingram M, Fraser R, Swan L, Hillis WS, Connell JM: Glucocorticoids contribute to the heritability of leptin in Scottish adult female twins. Clin Endocrinol (Oxf). 2004 Jul;61(1):149-54. [PubMed:15212658 ]
- Malunowicz EM, Romer TE, Urban M, Bossowski A: 11beta-hydroxysteroid dehydrogenase type 1 deficiency ('apparent cortisone reductase deficiency') in a 6-year-old boy. Horm Res. 2003;59(4):205-10. [PubMed:12649576 ]
- Melander O, Frandsen E, Groop L, Hulthen UL: No evidence of a relation between 11beta-hydroxysteroid dehydrogenase type 2 activity and salt sensitivity. Am J Hypertens. 2003 Sep;16(9 Pt 1):729-33. [PubMed:12944030 ]
- Vierhapper H, Nowotny P, Waldhausl W: Urinary steroid excretion rates in acromegaly. Horm Res. 2005;63(5):234-7. Epub 2005 May 17. [PubMed:15900108 ]
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