Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2007-04-12 19:06:39 UTC |
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Update Date | 2022-03-07 02:49:29 UTC |
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HMDB ID | HMDB0005972 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Tetrahydrodeoxycortisol |
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Description | Tetrahydrodeoxycortisol (THS) is a mineralocorticoid, the main urinary metabolite of 11-deoxycortisol. THS excretion is significantly associated with tetrahydroaldosterone excretion, total androgen excretion, and cortisol metabolites. Aldosterone synthesis is highly heritable and is affected by genotype at CYP11B1. Variation in the region of chromosome 8 including the genes steroid 11-beta-hydroxylase (CYP11B1) and aldosterone synthase (CYP11B2) influences mineralocorticoid and glucocorticoid metabolism; differences in 11-hydroxylation efficiency can have downstream effects on mineralocorticoid synthesis. Such effects may be of relevance to the development of low-renin essential hypertension. Genotype differences in CYP11B1 explains approximately 5% of the variance in urinary THS excretion in the population. Excretion of THS is heritable (19.4%) and the T-allele of the -344 C/T polymorphism of CYP11B2 is more strongly associated with higher THS levels than the C-allele. (PMID: 16984984 , 15522937 , 15272911 ). |
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Structure | [H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C InChI=1S/C21H34O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h13-17,22-23,25H,3-12H2,1-2H3/t13-,14-,15-,16+,17+,19+,20+,21+/m1/s1 |
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Synonyms | Value | Source |
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Tetrahydro-11-deoxycortisol | Kegg | 11-Deoxytetrahydrocortisol | HMDB | 3alpha,17alpha,21-Trihydroxy-5beta-pregnan-20-one | HMDB | 5beta-Pregnane-3alpha,17alpha,21-triol-20-one | HMDB | tetrahydro-S | HMDB | Tetrahydrocortexolone | HMDB | 5 beta-Pregnane-3alpha,17alpha,21-triol-20-one | MeSH, HMDB | tetrahydro Compound S | MeSH, HMDB | 3 alpha, 17,21-Trihydroxy-5 beta-pregnan-20-one | MeSH, HMDB | tetrahydro-Reichstein's substance S | MeSH, HMDB | Trihydroxypregnanone | MeSH, HMDB | 3alpha,5beta-THS | MeSH, HMDB |
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Chemical Formula | C21H34O4 |
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Average Molecular Weight | 350.4923 |
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Monoisotopic Molecular Weight | 350.245709576 |
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IUPAC Name | 1-[(1S,2S,5R,7R,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-hydroxyethan-1-one |
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Traditional Name | tetrahydro-s |
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CAS Registry Number | 68-60-0 |
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SMILES | [H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[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/C21H34O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h13-17,22-23,25H,3-12H2,1-2H3/t13-,14-,15-,16+,17+,19+,20+,21+/m1/s1 |
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InChI Key | UPTAPIKFKZGAGM-FAIYVORSSA-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
- 3-alpha-hydroxysteroid
- 17-hydroxysteroid
- Cyclic alcohol
- Tertiary alcohol
- Alpha-hydroxy ketone
- Ketone
- Secondary alcohol
- 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 | |
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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 | 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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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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Tetrahydrodeoxycortisol,1TMS,isomer #1 | C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO | 3121.7 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,1TMS,isomer #2 | C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C | 3069.5 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,1TMS,isomer #3 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO | 3087.0 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,1TMS,isomer #4 | C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C | 2993.6 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,2TMS,isomer #1 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO | 3123.4 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,2TMS,isomer #2 | C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C | 3155.3 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,2TMS,isomer #3 | C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C | 3066.3 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,2TMS,isomer #4 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C | 3100.4 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,2TMS,isomer #5 | C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3032.8 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,2TMS,isomer #6 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C | 3000.6 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,3TMS,isomer #1 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C | 3157.3 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,3TMS,isomer #2 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C | 3068.3 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,3TMS,isomer #3 | C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3137.0 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,3TMS,isomer #4 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3051.0 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,4TMS,isomer #1 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3123.7 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,4TMS,isomer #1 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3029.6 | Standard non polar | 33892256 | Tetrahydrodeoxycortisol,4TMS,isomer #1 | C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3344.5 | Standard polar | 33892256 | Tetrahydrodeoxycortisol,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]3CC[C@@]21C | 3383.3 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,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]3CC[C@@]21C | 3369.9 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@]4(O)C(=O)CO)[C@@H]3CC[C@@H]2C1 | 3353.4 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,1TBDMS,isomer #4 | 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]3CC[C@@]21C | 3270.4 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,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]3CC[C@@]21C | 3697.4 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@]4(O[Si](C)(C)C(C)(C)C)C(=O)CO)[C@@H]3CC[C@@H]2C1 | 3626.9 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,2TBDMS,isomer #3 | 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]3CC[C@@]21C | 3582.2 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,2TBDMS,isomer #4 | 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]3CC[C@@]21C | 3629.0 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,2TBDMS,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)CC[C@]4(C)[C@H]3CC[C@@]21C | 3538.7 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,2TBDMS,isomer #6 | 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]3CC[C@@]21C | 3503.2 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,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]3CC[C@@]21C | 3919.1 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,3TBDMS,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)CC[C@]4(C)[C@H]3CC[C@@]21C | 3899.0 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,3TBDMS,isomer #3 | 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]3CC[C@@]21C | 3806.2 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,3TBDMS,isomer #4 | 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]3CC[C@@]21C | 3780.7 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,4TBDMS,isomer #1 | 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]3CC[C@@]21C | 4101.7 | Semi standard non polar | 33892256 | Tetrahydrodeoxycortisol,4TBDMS,isomer #1 | 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]3CC[C@@]21C | 3826.1 | Standard non polar | 33892256 | Tetrahydrodeoxycortisol,4TBDMS,isomer #1 | 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]3CC[C@@]21C | 3623.1 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Tetrahydrodeoxycortisol EI-B (Non-derivatized) | splash10-00vi-1691000000-505dadab0d513b5e6ab3 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Tetrahydrodeoxycortisol EI-B (Non-derivatized) | splash10-00vi-1691000000-505dadab0d513b5e6ab3 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Tetrahydrodeoxycortisol GC-MS (Non-derivatized) - 70eV, Positive | splash10-05v3-4398000000-6a2c90339fca7bd2d7f4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Tetrahydrodeoxycortisol GC-MS (3 TMS) - 70eV, Positive | splash10-0udi-1014290000-45f9340b322c9f38f64a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Tetrahydrodeoxycortisol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | 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 - Tetrahydrodeoxycortisol 10V, Positive-QTOF | splash10-0f89-0029000000-2dafef0c1c57c19d1617 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetrahydrodeoxycortisol 20V, Positive-QTOF | splash10-00lu-0098000000-04fb94b06295b11c2c4b | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetrahydrodeoxycortisol 40V, Positive-QTOF | splash10-00fs-0491000000-808f4214bb9c8457d0ca | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetrahydrodeoxycortisol 10V, Negative-QTOF | splash10-0002-0019000000-f2cfd2cd5c4f89708bc9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetrahydrodeoxycortisol 20V, Negative-QTOF | splash10-05v4-3089000000-b615dbc2d0bb4012fa7a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetrahydrodeoxycortisol 40V, Negative-QTOF | splash10-0a4i-6093000000-32c633b5606b6e86a566 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetrahydrodeoxycortisol 10V, Negative-QTOF | splash10-00kb-0009000000-38d3f733587d36806d7a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetrahydrodeoxycortisol 20V, Negative-QTOF | splash10-0ldi-3029000000-63d6bbd371d07c340a6c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetrahydrodeoxycortisol 40V, Negative-QTOF | splash10-007c-0091000000-66ecef0bf396b725ea44 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetrahydrodeoxycortisol 10V, Positive-QTOF | splash10-0ue9-0009000000-de8ae4e2139ee50b1b49 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetrahydrodeoxycortisol 20V, Positive-QTOF | splash10-0002-0902000000-f8e993eaaffa04db0419 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tetrahydrodeoxycortisol 40V, Positive-QTOF | splash10-0002-2920000000-a342bcadbf94f1bae402 | 2021-09-22 | Wishart Lab | View Spectrum |
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General References | - Keavney B, Mayosi B, Gaukrodger N, Imrie H, Baker M, Fraser R, Ingram M, Watkins H, Farrall M, Davies E, Connell J: Genetic variation at the locus encompassing 11-beta hydroxylase and aldosterone synthase accounts for heritability in cortisol precursor (11-deoxycortisol) urinary metabolite excretion. J Clin Endocrinol Metab. 2005 Feb;90(2):1072-7. Epub 2004 Nov 2. [PubMed:15522937 ]
- Imrie H, Freel M, Mayosi BM, Davies E, Fraser R, Ingram M, Cordell HJ, Farrall M, Avery PJ, Watkins H, Keavney B, Connell JM: Association between aldosterone production and variation in the 11beta-hydroxylase (CYP11B1) gene. J Clin Endocrinol Metab. 2006 Dec;91(12):5051-6. Epub 2006 Sep 19. [PubMed:16984984 ]
- Kennon B, Ingram MC, Friel EC, Anderson NH, MacKenzie SM, Davies E, Shakerdi L, Wallace AM, Fraser R, Connell JM: Aldosterone synthase gene variation and adrenocortical response to sodium status, angiotensin II and ACTH in normal male subjects. Clin Endocrinol (Oxf). 2004 Aug;61(2):174-81. [PubMed:15272911 ]
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