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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 21:22:47 UTC |
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HMDB ID | HMDB0000949 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Tetrahydrocortisol |
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Description | Taurochenodesoxycholic acid, also known as chenodeoxycholoyltaurine or taurine chenodeoxycholate, belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety. Taurochenodesoxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
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Structure | |
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Synonyms | Value | Source |
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Taurochenodeoxycholic acid | Kegg | Chenodeoxycholoyltaurine | Kegg | Taurochenodeoxycholate | Generator | Taurochenodesoxycholate | Generator | Taurine chenodeoxycholate | HMDB | Taurine chenodeoxycholic acid | HMDB | 12-Deoxycholyltaurine | HMDB | 12-Desoxycholyltaurine | HMDB | 3a,7a-Dihydroxy-N-(2-sulfoethyl)-5b-cholan-24-amide | HMDB | Chenodeoxycholyltaurine | HMDB | Chenyltaurine | HMDB | N-(3a,7a-Dihydroxy-5b-cholan-24-oyl)-taurine | HMDB | Acid, taurochenodeoxycholic | HMDB | Chenodeoxycholate, taurine | HMDB | 2-Hydroxy-1-(3,11,17-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone | HMDB | 3a,11b,17,21-Tetrahydroxy-5b-pregnan-20-one | HMDB | 3b,11b,17,21-Tetrahydroxy-5b-pregnan-20-one | HMDB | 3b,11b,17a,21-Tetrahydroxy-5b-pregnan-20-ON | HMDB | 5b-Tetrahydrocortisol | HMDB | Dihydrocortison | HMDB | tetrahydro-Cortisol | HMDB | Urocortisol | 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-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one |
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Traditional Name | 2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethanone |
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CAS Registry Number | 53-02-1 |
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SMILES | C[C@]12C[C@H](O)C3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@]2(O)C(=O)CO |
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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+/m1/s1 |
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InChI Key | AODPIQQILQLWGS-OBRSLYEHSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety. |
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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 | Bile acids, alcohols and derivatives |
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Direct Parent | Taurinated bile acids and derivatives |
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Alternative Parents | |
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Substituents | - Taurinated bile acid
- Dihydroxy bile acid, alcohol, or derivatives
- Hydroxy bile acid, alcohol, or derivatives
- 3-hydroxysteroid
- Hydroxysteroid
- 3-alpha-hydroxysteroid
- 7-hydroxysteroid
- Fatty acyl
- Fatty amide
- N-acyl-amine
- Alkanesulfonic acid
- Cyclic alcohol
- Organic sulfonic acid or derivatives
- Organosulfonic acid or derivatives
- Organosulfonic acid
- Sulfonyl
- Secondary alcohol
- Secondary carboxylic acid amide
- Carboxamide group
- Carboxylic acid derivative
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Alcohol
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- 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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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 | Not Available | 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 | splash10-000j-3539000000-bf3e8ad7a2d21593e681 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-0fe3-1311189000-3a0cfdea998a0531cb8b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0019000000-5967aef805edb472d5a5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0532-0059000000-6e3db383f9bda6aa194a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01p9-1492000000-2266b6b18ef46f0eec05 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0009000000-5471dbe684b873e5784d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ap1-2039000000-d95c86b33b8f11b83354 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9086000000-0e28c8ffdf44e3e921fe | 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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Urine | Detected and Quantified | 0.19 (0.18-0.24) umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 0.14 (0.086-0.17) umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 0.21 +/- 0.038 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details |
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Abnormal Concentrations |
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Urine | Detected and Quantified | 0.20 +/- 0.023 umol/mmol creatinine | Adult (>18 years old) | Female | Eating disorder | | details | Urine | Detected and Quantified | 0.62 +/- 0.085 umol/mmol creatinine | Adult (>18 years old) | Female | Eating disorder | | details | Urine | Detected and Quantified | 0.00024 +/- 0.00020 umol/mmol creatinine | Adult (>18 years old) | Female | Stress urinary incontinence | | details |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB08833 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022335 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 343282 |
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KEGG Compound ID | C05465 |
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BioCyc ID | CHENODEOXYCHOLOYLTAURINE |
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BiGG ID | 45864 |
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Wikipedia Link | Not Available |
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METLIN ID | 5897 |
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PubChem Compound | 387316 |
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PDB ID | Not Available |
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ChEBI ID | 16525 |
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Food Biomarker Ontology | Not Available |
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VMH ID | TDCHOLA |
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MarkerDB ID | |
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References |
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Synthesis Reference | Gould, David H.; Oliveto, Eugene P. 17a-Hydroxycorticosterone and intermediates. (1957), US 2783254 19570226 CAN 51:62564 AN 1957:62564 |
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Material Safety Data Sheet (MSDS) | Not Available |
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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 ]
- 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 ]
- 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 ]
- Quinkler M, Zehnder D, Lepenies J, Petrelli MD, Moore JS, Hughes SV, Cockwell P, Hewison M, Stewart PM: Expression of renal 11beta-hydroxysteroid dehydrogenase type 2 is decreased in patients with impaired renal function. Eur J Endocrinol. 2005 Aug;153(2):291-9. [PubMed:16061836 ]
- 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 ]
- Rapetti S, Francia G, Iacono C, Martignoni G, Contessi G, Brunelli M, Galvanin F, Serio G: An unusual case of Cushing's syndrome due to ACTH-independent macronodular adrenal hyperplasia. Chir Ital. 2003 Mar-Apr;55(2):235-41. [PubMed:12744099 ]
- 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 ]
- Panin LE, Tuzikov FV, Gimautdinova OI: Tetrahydrocortisol-apolipoprotein A-I complex specifically interacts with eukaryotic DNA and GCC elements of genes. J Steroid Biochem Mol Biol. 2003 Dec;87(4-5):309-18. [PubMed:14698212 ]
- 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 ]
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