Record Information |
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Version | 5.0 |
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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 | 2022-03-07 02:49:03 UTC |
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HMDB ID | HMDB0000526 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 5alpha-Tetrahydrocortisol |
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Description | 5alpha-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 ). |
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Structure | [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 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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Synonyms | Value | Source |
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5a-Tetrahydrocortisol | Generator | 5Α-tetrahydrocortisol | Generator | 3,11,17,21-Tetrahydroxypregnan-20-one | HMDB | 3a,11b,17,21-Tetrahydroxy-5a-pregnan-20-one | HMDB | 3a,11b,17a,21-Tetrahydroxy-5a-pregnan-20-one | HMDB | 3a,5a-Tetrahydrocortisol | HMDB | 3a-Allotetrahydrocortisol | HMDB | 3alpha, 5alpha-Tetrahydrocortisol | HMDB | 3alpha,5alpha-Tetrahydrocortisol | HMDB | 5a-Pregnane-3a,11b,17a,21-tetraol-20-one | HMDB | 5a-Pregnane-3a,11b,17a,21-tetrol-20-one | HMDB | a-THF | HMDB | Allo-3a-tetrahydrocortisol | HMDB | Allo-3alpha-tetrahydrocortisol | HMDB | Allo-tetrahydrocortisol | HMDB | Allopregnane-3a,11b,17a,21-tetrol-20-one | HMDB | Allopregnane-3a,11b,21-tetrol-20-one | HMDB | Allopregnane-3alpha,11beta,17alpha,21-tetrol-20-one | HMDB | Allotetrahydro-compound F | HMDB | Allotetrahydro-cortisol | HMDB | Allotetrahydrocompound F | HMDB | Allotetrahydrocortisol | HMDB | alpha-THF | HMDB | ATHF | HMDB | Kendall'S compound c | HMDB | Reichstein'S substance C | HMDB | Tetrahydro-allocortisol | HMDB | Tetrahydroallocortisol | HMDB | Wintersteiner'S compound D | HMDB | Allotetrahydrocortisol, (3beta,5alpha,11beta)-isomer | HMDB | 5AlphaTHF | HMDB | Allotetrahydrocortisol, (3alpha,5beta,11alpha)-isomer | HMDB | Allotetrahydrocortisol, (5alpha,11beta)-isomer | HMDB | Allotetrahydrocortisol, (3beta,5beta,11beta)-isomer | HMDB | (3alpha,5alpha,11beta)-3,11,17,21-Tetrahydroxypregnan-20-one | HMDB | (3Α,5α,11β)-3,11,17,21-tetrahydroxypregnan-20-one | HMDB | 3alpha,11beta,17,21-Tetrahydroxy-5alpha-pregnan-20-one | HMDB | 3alpha,11beta,17alpha,21-Tetrahydroxy-5alpha-pregnan-20-one | HMDB | 3Α,11β,17,21-tetrahydroxy-5α-pregnan-20-one | HMDB | 3Α,11β,17α,21-tetrahydroxy-5α-pregnan-20-one | HMDB | 3Α,5α-tetrahydrocortisol | HMDB | 5alpha-Pregnane-3alpha,11beta,17alpha,21-tetraol-20-one | HMDB | 5alpha-Pregnane-3alpha,11beta,17alpha,21-tetrol-20-one | HMDB | 5alpha-THF | HMDB | 5Α-pregnane-3α,11β,17α,21-tetraol-20-one | HMDB | 5Α-pregnane-3α,11β,17α,21-tetrol-20-one | HMDB | 5Α-THF | HMDB | Allopregnane-3α,11β,17α,21-tetrol-20-one | HMDB | Allo-3α-tetrahydrocortisol | HMDB | Α-THF | HMDB | 5alpha-Tetrahydrocortisol | HMDB |
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Chemical Formula | C21H34O5 |
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Average Molecular Weight | 366.4917 |
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Monoisotopic Molecular Weight | 366.240624198 |
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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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Traditional 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]ethanone |
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CAS Registry Number | 302-91-0 |
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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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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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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
- 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 | |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 244.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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5alpha-Tetrahydrocortisol,1TMS,isomer #1 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO | 3241.4 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,1TMS,isomer #2 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C | 3187.9 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,1TMS,isomer #3 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO | 3127.6 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,1TMS,isomer #4 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO | 3205.2 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,1TMS,isomer #5 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C | 3152.1 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TMS,isomer #1 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO | 3208.7 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TMS,isomer #10 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C | 3111.6 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TMS,isomer #2 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO | 3115.0 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TMS,isomer #3 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C | 3252.2 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TMS,isomer #4 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C | 3170.0 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TMS,isomer #5 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C | 3182.9 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TMS,isomer #6 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C | 3088.8 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TMS,isomer #7 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3151.4 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TMS,isomer #8 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO | 3062.5 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TMS,isomer #9 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C | 3050.3 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TMS,isomer #1 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO | 3099.3 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TMS,isomer #10 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C | 3021.8 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TMS,isomer #2 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C | 3217.6 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TMS,isomer #3 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C | 3125.0 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TMS,isomer #4 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C | 3138.6 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TMS,isomer #5 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C | 3074.1 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TMS,isomer #6 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3187.6 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TMS,isomer #7 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C | 3070.1 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TMS,isomer #8 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3108.6 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TMS,isomer #9 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3054.6 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,4TMS,isomer #1 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C | 3136.3 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,4TMS,isomer #2 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C | 3068.9 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,4TMS,isomer #3 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3154.4 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,4TMS,isomer #4 | C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3111.0 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,4TMS,isomer #5 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3040.2 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,5TMS,isomer #1 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3092.9 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,5TMS,isomer #1 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3097.9 | Standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,5TMS,isomer #1 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3333.8 | Standard polar | 33892256 | 5alpha-Tetrahydrocortisol,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 3496.9 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 3472.2 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)[C@@H](CC[C@]2(O)C(=O)CO)[C@@H]2CC[C@H]3C[C@H](O)CC[C@]3(C)[C@@H]12 | 3380.9 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,1TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]3CC[C@]2(O)C(=O)CO)C1 | 3451.3 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,1TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 3388.7 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 3755.2 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TBDMS,isomer #10 | CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 3575.2 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]3CC[C@]2(O[Si](C)(C)C(C)(C)C)C(=O)CO)C1 | 3690.1 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)[C@@H](CC[C@]2(O[Si](C)(C)C(C)(C)C)C(=O)CO)[C@@H]2CC[C@H]3C[C@H](O)CC[C@]3(C)[C@@H]12 | 3591.6 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 3644.0 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 3684.2 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3590.8 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TBDMS,isomer #7 | CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 3622.3 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TBDMS,isomer #8 | CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)[C@@H](CC[C@]2(O)C(=O)CO)[C@@H]2CC[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]3(C)[C@@H]12 | 3524.5 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,2TBDMS,isomer #9 | CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3499.5 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 3952.6 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TBDMS,isomer #10 | CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3675.8 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3832.4 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 3880.0 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)[C@@H](CC[C@]2(O[Si](C)(C)C(C)(C)C)C(=O)CO)[C@@H]2CC[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]3(C)[C@@H]12 | 3752.5 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 3830.5 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3753.3 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TBDMS,isomer #7 | CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3733.7 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TBDMS,isomer #8 | CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 3805.4 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,3TBDMS,isomer #9 | CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3721.8 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3978.6 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,4TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 4074.6 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,4TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3968.4 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,4TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3934.2 | Semi standard non polar | 33892256 | 5alpha-Tetrahydrocortisol,4TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C | 3875.1 | Semi standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (Non-derivatized) - 70eV, Positive | splash10-000j-3539000000-d7581fc3650c2eb0185b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (4 TMS) - 70eV, Positive | splash10-000l-1200139000-f34c6af9d49af972f03b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_1_5) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_6) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_7) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_8) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_9) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_10) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_4) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_5) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_6) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_7) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 10V, Positive-QTOF | splash10-0002-0019000000-5967aef805edb472d5a5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 20V, Positive-QTOF | splash10-0532-0059000000-6e3db383f9bda6aa194a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 40V, Positive-QTOF | splash10-01p9-1492000000-2266b6b18ef46f0eec05 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 10V, Negative-QTOF | splash10-014i-0009000000-5471dbe684b873e5784d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 20V, Negative-QTOF | splash10-0ap1-2039000000-d95c86b33b8f11b83354 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 40V, Negative-QTOF | splash10-0a4i-9086000000-0e28c8ffdf44e3e921fe | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 10V, Negative-QTOF | splash10-014i-0009000000-8339b94cd560c336a8d4 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 20V, Negative-QTOF | splash10-014i-2009000000-76e08d0eac5051f615bf | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 40V, Negative-QTOF | splash10-100c-0039000000-af1a66b3967a8f31e2d4 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 10V, Positive-QTOF | splash10-015a-0009000000-249d6f44172a375b08be | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 20V, Positive-QTOF | splash10-014i-1902000000-95c98bcfe0691617e5b5 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 40V, Positive-QTOF | splash10-00kb-8980000000-ea48ab8fad3384d8e0c6 | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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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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Urine | Detected and Quantified | 0.14 (0.10-0.16) umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 0.071 (0.048-0.095) umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 0.19 +/- 0.026 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 | 0.13 +/- 0.029 umol/mmol creatinine | Adult (>18 years old) | Female | Eating disorder | | details | Urine | Detected and Quantified | 0.65 +/- 0.14 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 | FDB022094 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 83726 |
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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 | Not Available |
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METLIN ID | 5511 |
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PubChem Compound | 92748 |
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PDB ID | Not Available |
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ChEBI ID | 89627 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Fukushima, David K.; Daum, Sol. Synthesis of Reichstein's substance C and related compounds. Journal of Organic Chemistry (1961), 26 520-3. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
- Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. [PubMed:14625002 ]
- 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 ]
- Kerstens MN, van der Kleij FG, Boonstra AH, Sluiter WJ, van der Molen JC, Navis G, Dullaart RP: Angiotensin administration stimulates renal 11 beta-hydroxysteroid dehydrogenase activity in healthy men. Kidney Int. 2004 Jun;65(6):2065-70. [PubMed:15149319 ]
- Mantero F, Palermo M, Petrelli MD, Tedde R, Stewart PM, Shackleton CH: Apparent mineralocorticoid excess: type I and type II. Steroids. 1996 Apr;61(4):193-6. [PubMed:8732999 ]
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