Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-05-22 18:26:21 UTC |
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Update Date | 2022-03-07 02:49:30 UTC |
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HMDB ID | HMDB0006227 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 1-a,24R,25-Trihydroxyvitamin D2 |
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Description | 1-alpha,24R,25-Trihydroxyvitamin D2 is a metabolite of vitamin D2 produced in vitro by perfusing isolated rat kidneys with 1,25-dihydroxyvitamin D2. It has been well established that 1,25-dihydroxyvitamin D3 is converted into various further metabolites in the kidney as a result of chemical reactions such as C-23, C-24, and C-26 hydroxylations, C-24 ketonization, and C-23:C-26 lactonization. (PMID: 3490274 ). |
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Structure | [H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C)[C@H](C)\C=C\[C@@](C)(O)C(C)(C)O InChI=1S/C28H44O4/c1-18(13-15-28(6,32)26(3,4)31)23-11-12-24-20(8-7-14-27(23,24)5)9-10-21-16-22(29)17-25(30)19(21)2/h9-10,13,15,18,22-25,29-32H,2,7-8,11-12,14,16-17H2,1,3-6H3/b15-13+,20-9+,21-10-/t18-,22-,23-,24+,25+,27-,28-/m1/s1 |
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Synonyms | Value | Source |
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(24R)-1alpha,24,25-Trihydroxyergocalciferol | HMDB | (24R)-1alpha,24,25-Trihydroxyvitamin D2 | HMDB | (5Z,7E,22E)-(1S,3R,24R)-9,10-Seco-5,7,10(19),22-ergostatetraene-1,3,24,25-tetrol | HMDB | 1-alpha,24R,25-Trihydroxyvitamin D2 | HMDB | 1,24,25-Trihydroxyergocalciferol | HMDB | 1,24,25-Trihydroxyvitamin D2 | HMDB | (24R)-1a,24,25-Trihydroxyvitamin D2 / (24R)-1a,24,25-trihydroxyergocalciferol | HMDB | (24R)-1Α,24,25-trihydroxyvitamin D2 / (24R)-1α,24,25-trihydroxyergocalciferol | HMDB |
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Chemical Formula | C28H44O4 |
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Average Molecular Weight | 444.6466 |
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Monoisotopic Molecular Weight | 444.323959896 |
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IUPAC Name | (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dihydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol |
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Traditional Name | (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dihydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol |
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CAS Registry Number | Not Available |
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SMILES | C[C@H](\C=C\[C@@](C)(O)C(C)(O)C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C |
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InChI Identifier | InChI=1S/C28H44O4/c1-18(13-15-28(6,32)26(3,4)31)23-11-12-24-20(8-7-14-27(23,24)5)9-10-21-16-22(29)17-25(30)19(21)2/h9-10,13,15,18,22-25,29-32H,2,7-8,11-12,14,16-17H2,1,3-6H3/b15-13+,20-9+,21-10-/t18-,22-,23-,24+,25+,27-,28-/m1/s1 |
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InChI Key | KRGCLKZOZQUAFK-ABEKVIRTSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. |
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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 | Vitamin D and derivatives |
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Direct Parent | Vitamin D and derivatives |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- 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 | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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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 | | 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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1-a,24R,25-Trihydroxyvitamin D2,1TMS,isomer #1 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C)C(C)(C)O)C[C@@H](O)C[C@@H]1O | 3667.7 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,1TMS,isomer #2 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O[Si](C)(C)C)C[C@@H](O)C[C@@H]1O | 3650.5 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,1TMS,isomer #3 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O)C[C@@H](O[Si](C)(C)C)C[C@@H]1O | 3603.7 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,1TMS,isomer #4 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O)C[C@@H](O)C[C@@H]1O[Si](C)(C)C | 3597.1 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,2TMS,isomer #1 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C)C(C)(C)O[Si](C)(C)C)C[C@@H](O)C[C@@H]1O | 3683.5 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,2TMS,isomer #2 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C)C(C)(C)O)C[C@@H](O[Si](C)(C)C)C[C@@H]1O | 3575.8 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,2TMS,isomer #3 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C)C(C)(C)O)C[C@@H](O)C[C@@H]1O[Si](C)(C)C | 3562.9 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,2TMS,isomer #4 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O | 3572.3 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,2TMS,isomer #5 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O[Si](C)(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C | 3562.5 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,2TMS,isomer #6 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C | 3489.5 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,3TMS,isomer #1 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C)C(C)(C)O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O | 3590.5 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,3TMS,isomer #2 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C)C(C)(C)O[Si](C)(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C | 3566.4 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,3TMS,isomer #3 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C)C(C)(C)O)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C | 3480.9 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,3TMS,isomer #4 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C | 3478.4 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,4TMS,isomer #1 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C)C(C)(C)O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C | 3496.4 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,1TBDMS,isomer #1 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)O)C[C@@H](O)C[C@@H]1O | 3899.3 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,1TBDMS,isomer #2 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O[Si](C)(C)C(C)(C)C)C[C@@H](O)C[C@@H]1O | 3885.7 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,1TBDMS,isomer #3 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O | 3809.4 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,1TBDMS,isomer #4 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3789.2 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,2TBDMS,isomer #1 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)O[Si](C)(C)C(C)(C)C)C[C@@H](O)C[C@@H]1O | 4154.9 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,2TBDMS,isomer #2 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)O)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O | 4025.8 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,2TBDMS,isomer #3 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)O)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3992.7 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,2TBDMS,isomer #4 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O | 4024.0 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,2TBDMS,isomer #5 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O[Si](C)(C)C(C)(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3991.7 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,2TBDMS,isomer #6 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3888.8 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,3TBDMS,isomer #1 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O | 4291.9 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,3TBDMS,isomer #2 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)O[Si](C)(C)C(C)(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 4245.8 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,3TBDMS,isomer #3 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)O)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C | 4123.7 | Semi standard non polar | 33892256 | 1-a,24R,25-Trihydroxyvitamin D2,3TBDMS,isomer #4 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@](C)(O)C(C)(C)O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C | 4121.2 | 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 - 1-a,24R,25-Trihydroxyvitamin D2 GC-MS (Non-derivatized) - 70eV, Positive | splash10-056u-7029800000-43c6234d3e656296a1b6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 GC-MS (3 TMS) - 70eV, Positive | splash10-000t-4500239000-0e3ca1deb7889de812d2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 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 - 1-a,24R,25-Trihydroxyvitamin D2 10V, Positive-QTOF | splash10-056r-0103900000-067d5d23ea26f466bf5d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 20V, Positive-QTOF | splash10-0a6r-0429500000-69efc694ba58cb419b89 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 40V, Positive-QTOF | splash10-0629-2869300000-930214312165d85c4365 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 10V, Negative-QTOF | splash10-0006-0000900000-110d72ce2473020c6e5b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 20V, Negative-QTOF | splash10-016u-0009500000-81a9ee0dd2187b54fac2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 40V, Negative-QTOF | splash10-0f79-9606400000-89f03acf9363d9fc866b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 10V, Positive-QTOF | splash10-05p9-0190500000-d24d16d15f07a8f79302 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 20V, Positive-QTOF | splash10-014r-0192200000-cd17b1d2f071ca718665 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 40V, Positive-QTOF | splash10-000i-3982000000-8ec0ccf910b01083d65d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 10V, Negative-QTOF | splash10-0006-0000900000-acb02db005364f8f10b0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 20V, Negative-QTOF | splash10-0f6x-4905800000-e3d866c123903cdcb502 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-a,24R,25-Trihydroxyvitamin D2 40V, Negative-QTOF | splash10-014i-1319400000-8f896636eeaea36b25ab | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane
- Mitochondria
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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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 | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB112230 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 7826193 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | 2290317 |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 9547253 |
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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 | 1A2425THVITD2 |
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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 | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Reddy GS, Tserng KY: Isolation and identification of 1,24,25-trihydroxyvitamin D2, 1,24,25,28-tetrahydroxyvitamin D2, and 1,24,25,26-tetrahydroxyvitamin D2: new metabolites of 1,25-dihydroxyvitamin D2 produced in rat kidney. Biochemistry. 1986 Sep 9;25(18):5328-36. [PubMed:3490274 ]
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