Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:08:25 UTC |
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Update date | 2015-07-21 06:56:58 UTC |
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Primary ID | FDB022094 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 5a-Tetrahydrocortisol |
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Description | 5a-Tetrahydrocortisol is a normal human metabolite. However its increased ratio (5alpha-Tetrahydrocortisol + Tetrahydrocortisol) over Tetrahydrocortisone in urine is the biochemical marker for the syndrome of apparent mineralocorticoid excess (AME). AME is a heritable form of hypertension due to an inborn error of cortisol metabolism and is characterized by hypokalemia and low renin levels despite subnormal or normal levels of aldosterone and other known mineralocorticoids. The syndrome is attributable to congenital deficiency of the enzyme 11 beta-hydroxydehydrogenase (11 beta-HSD), which converts cortisol to biologically inactive cortisone. This results in a prolonged half-life of Cortisol, which acts at the kidney level as a potent mineralocorticoid. (PMID: 8732999) [HMDB] |
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CAS Number | 302-91-0 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C21H34O5 |
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IUPAC name | 2-hydroxy-1-[(1S,2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one |
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InChI Identifier | InChI=1S/C21H34O5/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/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18+,19-,20-,21-/m0/s1 |
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InChI Key | AODPIQQILQLWGS-FDSHTENPSA-N |
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Isomeric SMILES | [H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C |
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Average Molecular Weight | 366.4917 |
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Monoisotopic Molecular Weight | 366.240624198 |
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Classification |
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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
- Oxosteroid
- 11-beta-hydroxysteroid
- 11-hydroxysteroid
- 3-alpha-hydroxysteroid
- 17-hydroxysteroid
- Tertiary alcohol
- Alpha-hydroxy ketone
- Cyclic alcohol
- Ketone
- Secondary alcohol
- Polyol
- Primary alcohol
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | - C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030200 )
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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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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | 5a-Tetrahydrocortisol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000j-3539000000-d7581fc3650c2eb0185b | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000l-1200139000-f34c6af9d49af972f03b | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_3_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 5a-Tetrahydrocortisol, TMS_3_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0019000000-5967aef805edb472d5a5 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0532-0059000000-6e3db383f9bda6aa194a | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01p9-1492000000-2266b6b18ef46f0eec05 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0009000000-5471dbe684b873e5784d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ap1-2039000000-d95c86b33b8f11b83354 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9086000000-0e28c8ffdf44e3e921fe | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0009000000-8339b94cd560c336a8d4 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-2009000000-76e08d0eac5051f615bf | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-100c-0039000000-af1a66b3967a8f31e2d4 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-015a-0009000000-249d6f44172a375b08be | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-1902000000-95c98bcfe0691617e5b5 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kb-8980000000-ea48ab8fad3384d8e0c6 | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 83726 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 92748 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00526 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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