Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-07-11 15:20:21 UTC |
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Update Date | 2022-03-07 02:49:32 UTC |
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HMDB ID | HMDB0006720 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 23S,25-dihydroxyvitamin D3 |
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Description | 23S,25-dihydroxyvitamin D3 (23S,25-(OH)2D3) is a circulating metabolite of vitamin D3 during vitamin D excess. During hypocalcemia or hypovitaminosis D, 25-OH-D3 is 1alpha-hydroxylated, primarily in kidney, to produce 1,25-(OH)2D3. 1,25-(OH)2D3 is a hormonally active form of vitamin D3 that enhances intestinal calcium transport and promotes mobilization of calcium from bone. In states of vitamin D excess, other pathways of 25-OH-D3 metabolism emerge as alternatives to 1-and 24-hydroxylation. Recently, 25-hydroxyvitamin D3-26,23-lactone (lactone) was identified as a major plasma metabolite in animals receiving large doses of vitamin D. Although the function of the lactone is not known, its 5-fold greater potency of binding to the plasma vitamin D carrier protein, relative to 25-OH-D3, suggests that it may, perhaps indirectly, contribute to vitamin D toxicity. This indicates the existence of an alternate route to lactone formation through a new 25-OH-D3 metabolite, 23,25-(OH)2D3. (PMID: 6286629 ). |
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Structure | OC(C[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1\C[C@H](O)CCC1=C)CC(O)(C)C InChI=1S/C27H44O3/c1-18-8-11-22(28)16-21(18)10-9-20-7-6-14-27(5)24(12-13-25(20)27)19(2)15-23(29)17-26(3,4)30/h9-10,19,22-25,28-30H,1,6-8,11-17H2,2-5H3/b20-9+,21-10-/t19-,22-,23?,24-,25?,27-/m1/s1 |
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Synonyms | Value | Source |
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(3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,23,25-triol | HMDB | 23,25-Dihydroxycholecalciferol | HMDB | 23,25-Dihydroxyvitamin D3 | HMDB | 23S,25-Dihydroxyvitamin D | HMDB | 23,25-Dihydroxyvitamin D3, (3beta,5Z,7E,23R)-isomer | MeSH, HMDB | 23S, 25 Dihydroxyvitamin D | MeSH, HMDB | 23,25-Dihydroxyvitamin D3, (3beta,5Z,7E,23S)-isomer | MeSH, HMDB | 23S,25-Dihydroxyvitamin D3 | MeSH |
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Chemical Formula | C27H44O3 |
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Average Molecular Weight | 416.6365 |
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Monoisotopic Molecular Weight | 416.329045274 |
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IUPAC Name | (6R)-6-[(1R,4E,7aR)-4-{2-[(1Z,5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,4-diol |
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Traditional Name | 23,25-dihydroxyvitamin d3 |
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CAS Registry Number | 77733-16-5 |
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SMILES | OC(C[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1\C[C@H](O)CCC1=C)CC(O)(C)C |
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InChI Identifier | InChI=1S/C27H44O3/c1-18-8-11-22(28)16-21(18)10-9-20-7-6-14-27(5)24(12-13-25(20)27)19(2)15-23(29)17-26(3,4)30/h9-10,19,22-25,28-30H,1,6-8,11-17H2,2-5H3/b20-9+,21-10-/t19-,22-,23?,24-,25?,27-/m1/s1 |
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InChI Key | JVBPQHSRTHJMLM-UXHBOMOISA-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 | Not Available |
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Ontology |
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Physiological effect | Not Available |
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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 | | 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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23S,25-dihydroxyvitamin D3,1TMS,isomer #1 | C=C1CC[C@@H](O)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O)O[Si](C)(C)C | 3417.7 | Semi standard non polar | 33892256 | 23S,25-dihydroxyvitamin D3,1TMS,isomer #2 | C=C1CC[C@@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(O)CC(C)(C)O | 3427.4 | Semi standard non polar | 33892256 | 23S,25-dihydroxyvitamin D3,1TMS,isomer #3 | C=C1CC[C@@H](O)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(O)CC(C)(C)O[Si](C)(C)C | 3498.9 | Semi standard non polar | 33892256 | 23S,25-dihydroxyvitamin D3,2TMS,isomer #1 | C=C1CC[C@@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O)O[Si](C)(C)C | 3365.7 | Semi standard non polar | 33892256 | 23S,25-dihydroxyvitamin D3,2TMS,isomer #2 | C=C1CC[C@@H](O)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C | 3472.8 | Semi standard non polar | 33892256 | 23S,25-dihydroxyvitamin D3,2TMS,isomer #3 | C=C1CC[C@@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(O)CC(C)(C)O[Si](C)(C)C | 3473.5 | Semi standard non polar | 33892256 | 23S,25-dihydroxyvitamin D3,3TMS,isomer #1 | C=C1CC[C@@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C | 3460.9 | Semi standard non polar | 33892256 | 23S,25-dihydroxyvitamin D3,1TBDMS,isomer #1 | C=C1CC[C@@H](O)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O)O[Si](C)(C)C(C)(C)C | 3655.5 | Semi standard non polar | 33892256 | 23S,25-dihydroxyvitamin D3,1TBDMS,isomer #2 | C=C1CC[C@@H](O[Si](C)(C)C(C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(O)CC(C)(C)O | 3632.2 | Semi standard non polar | 33892256 | 23S,25-dihydroxyvitamin D3,1TBDMS,isomer #3 | C=C1CC[C@@H](O)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(O)CC(C)(C)O[Si](C)(C)C(C)(C)C | 3725.1 | Semi standard non polar | 33892256 | 23S,25-dihydroxyvitamin D3,2TBDMS,isomer #1 | C=C1CC[C@@H](O[Si](C)(C)C(C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O)O[Si](C)(C)C(C)(C)C | 3815.5 | Semi standard non polar | 33892256 | 23S,25-dihydroxyvitamin D3,2TBDMS,isomer #2 | C=C1CC[C@@H](O)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3951.3 | Semi standard non polar | 33892256 | 23S,25-dihydroxyvitamin D3,2TBDMS,isomer #3 | C=C1CC[C@@H](O[Si](C)(C)C(C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(O)CC(C)(C)O[Si](C)(C)C(C)(C)C | 3929.2 | Semi standard non polar | 33892256 | 23S,25-dihydroxyvitamin D3,3TBDMS,isomer #1 | C=C1CC[C@@H](O[Si](C)(C)C(C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4175.7 | 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 - 23S,25-dihydroxyvitamin D3 GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4j-4029200000-3128bb61534e2a427697 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 23S,25-dihydroxyvitamin D3 GC-MS (3 TMS) - 70eV, Positive | splash10-014i-1312129000-e13f5e28078d0804d5fd | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 23S,25-dihydroxyvitamin D3 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 - 23S,25-dihydroxyvitamin D3 10V, Positive-QTOF | splash10-001j-0009100000-725d99dd1a03900a439e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 20V, Positive-QTOF | splash10-003v-2239000000-a0d3af884fa9abdf21db | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 40V, Positive-QTOF | splash10-05j1-3297000000-75bac1132fc7efc86430 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 10V, Negative-QTOF | splash10-014i-1009800000-18157637f9387fd32fbf | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 20V, Negative-QTOF | splash10-00r2-3009200000-f2b1c6855bc0131956df | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 40V, Negative-QTOF | splash10-00di-9002000000-7f4b7d1cf6b42ba1dfd6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 10V, Positive-QTOF | splash10-00ke-0239300000-d4abedc6c1157555a1b3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 20V, Positive-QTOF | splash10-00di-1395000000-21974a8e6168517fbdfd | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 40V, Positive-QTOF | splash10-05fs-1961000000-b05c3941e9ab3a0a43a9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 10V, Negative-QTOF | splash10-014i-0002900000-742f0877fc75cd43c6a5 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 20V, Negative-QTOF | splash10-00kb-1109200000-08d969be5480c95cb00c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 40V, Negative-QTOF | splash10-03g0-1329400000-acc5b6dbb606ad5a7880 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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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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| Not Available |
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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 | FDB024038 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 35016021 |
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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 | Not Available |
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PubChem Compound | 13072270 |
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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 | CE2201 |
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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 | - Napoli JL, Pramanik BC, Partridge JJ, Uskokovic MR, Horst RL: 23S,25-dihydroxyvitamin D3 as a circulating metabolite of vitamin D3. Its role in 25-hydroxyvitamin D3-26,23-lactone biosynthesis. J Biol Chem. 1982 Aug 25;257(16):9634-9. [PubMed:6286629 ]
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