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 15:36:18 UTC |
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Update Date | 2022-03-07 02:49:32 UTC |
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HMDB ID | HMDB0006721 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 5,6-trans-25-Hydroxyvitamin D3 |
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Description | 5,6-trans-25-Hydroxyvitamin D3 is a vitamin D3 derivative, and is found in normal plasma. 5,6-trans-25-Hydroxyvitamin D3 is a 25-hydroxylated metabolite of the secosteroid that is active in inhibiting 3H-thymidine incorporation into cultured normal human keratinocytes. The evidence strongly supports the existence of a heretofore unknown metabolic route in vitamin DS metabolism, namely, the conversion of 5,6-cis compounds to 5,6-trans compounds. The mechanism of this transformation is not clear at present; it could be enzymatic or nonenzymatic. The site of formation of 5,6-trans-25-hydroxyvitamin D3 is unknown. (PMID 6256855 , 10876100 , 6270082 ). |
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Structure | C[C@H](CCCC(O)(C)C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C/C=C1\C[C@H](O)CCC1=C InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11-,22-12+/t20-,23-,24-,25?,27-/m1/s1 |
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Synonyms | Value | Source |
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(3b,5E,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diol | HMDB | (3beta,5E,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diol | HMDB | 25-Hydroxy-5,6-trans-cholecalciferol | HMDB | 25-Hydroxy-5,6-trans-vitamin D3 | HMDB | 5,6-trans-25-Hydroxycholecalciferol | HMDB |
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Chemical Formula | C27H44O2 |
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Average Molecular Weight | 400.6371 |
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Monoisotopic Molecular Weight | 400.334130652 |
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IUPAC Name | (1R,3E)-3-{2-[(1R,4Z,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol |
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Traditional Name | 5,6-trans-25-hydroxyvitamin D3 |
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CAS Registry Number | 36149-00-5 |
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SMILES | C[C@H](CCCC(O)(C)C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C/C=C1\C[C@H](O)CCC1=C |
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InChI Identifier | InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11-,22-12+/t20-,23-,24-,25?,27-/m1/s1 |
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InChI Key | JWUBBDSIWDLEOM-ZMHTYULMSA-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 | 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 | |
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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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5,6-trans-25-Hydroxyvitamin 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)CCCC(C)(C)O[Si](C)(C)C | 3389.6 | Semi standard non polar | 33892256 | 5,6-trans-25-Hydroxyvitamin 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)CCCC(C)(C)O | 3268.4 | Semi standard non polar | 33892256 | 5,6-trans-25-Hydroxyvitamin 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)CCCC(C)(C)O[Si](C)(C)C | 3388.0 | Semi standard non polar | 33892256 | 5,6-trans-25-Hydroxyvitamin 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)CCCC(C)(C)O[Si](C)(C)C(C)(C)C | 3626.3 | Semi standard non polar | 33892256 | 5,6-trans-25-Hydroxyvitamin 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)CCCC(C)(C)O | 3473.9 | Semi standard non polar | 33892256 | 5,6-trans-25-Hydroxyvitamin 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)CCCC(C)(C)O[Si](C)(C)C(C)(C)C | 3857.9 | Semi standard non polar | 33892256 |
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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 - 5,6-trans-25-Hydroxyvitamin D3 GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ab9-3029000000-4c75b5cfbc422ba2a344 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 GC-MS (2 TMS) - 70eV, Positive | splash10-003r-1403290000-a8eb9294a6df1ce864d2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5,6-trans-25-Hydroxyvitamin 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 - 5,6-trans-25-Hydroxyvitamin D3 10V, Positive-QTOF | splash10-00lr-0119100000-c93e02f4cad435f61273 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 20V, Positive-QTOF | splash10-0aw9-1369000000-cbcc10bc94de9ec9da1b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 40V, Positive-QTOF | splash10-05ai-5297000000-3c05eab14ebbc9c770e8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 10V, Negative-QTOF | splash10-0002-0009000000-cc66843e9af0092a8e53 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 20V, Negative-QTOF | splash10-000t-0009000000-3efda332aebefe04f7ed | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 40V, Negative-QTOF | splash10-00si-1129000000-ee8ae09159fb7ba45063 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 10V, Positive-QTOF | splash10-001i-0549100000-7e0d15fb33d297cd7b9d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 20V, Positive-QTOF | splash10-0g4i-5494100000-ac59f398e11b390f5b2d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 40V, Positive-QTOF | splash10-0ab9-1940000000-65e563c113f344b0c1b6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 10V, Negative-QTOF | splash10-0002-0009000000-6962dcfe00557f780ffe | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 20V, Negative-QTOF | splash10-0002-0109000000-479fbd2eb75d5147bbc7 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 40V, Negative-QTOF | splash10-01pk-0339000000-a9adae13919854810a00 | 2021-09-23 | Wishart Lab | View Spectrum |
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