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 18:21:38 UTC |
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Update Date | 2022-03-07 02:49:30 UTC |
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HMDB ID | HMDB0006226 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 24R,25-Dihydroxyvitamin D3 |
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Description | 24R,25-Dihydroxyvitamin D3, also known as 24(R),25(OH)2D3, is a vitamin D metabolite; a dihydroxylated form of the seco-steroid. With the identification of a target cell, the growth plate resting zone (RC) chondrocyte, studies indicate that there are specific membrane-associated signal transduction pathways that mediate both rapid, nongenomic, and genomic responses of RC cells to 24(R),25(OH)2D3. These studies indicate that 24(R),25(OH)2D3 plays an important role in endochondral ossification by regulating less mature chondrocytes and promoting their maturation in the endochondral lineage. 24(R),25(OH)2D3 binds RC chondrocyte membranes with high specificity, increasing protein kinase C (PKC) activity. The effect is stereospecific; 24R,25(OH)2D3, but not 24S,25(OH)2D3, causes the increase, indicating a receptor-mediated response. Phospholipase D-2 (PLD2) activity is increased, resulting in increased production of diacylglycerol (DAG), which in turn activates PKC. 24(R),25(OH)2D3 does not cause translocation of PKC to the plasma membrane but activates existing PKCα. There is a rapid decrease in Ca2+ efflux, and the influx is stimulated. 24(R),25(OH)2D3 also reduces arachidonic acid release by decreasing phospholipase A2 (PLA2) activity, thereby decreasing the available substrate for prostaglandin production via the action of cyclooxygenase-1. PGE2 that is produced acts on the EP1 and EP2 receptors expressed by RC cells to downregulate PKC via protein kinase A, but the reduction in PGE2 decreases this negative feedback mechanism. Both pathways converge on MAP kinase, leading to new gene expression. One consequence of this is the production of new matrix vesicles containing PKCα and PKCγ, and an increase in PKC activity. The chondrocytes also produce 24(R),25(OH)2D3, and the secreted metabolite acts directly on the matrix vesicle membrane. Only PKCγ is directly affected by 24(R),25(OH)2D3 in the matrix vesicles, and activity of this isoform is inhibited. This effect may be involved in the control of matrix maturation and turnover. 24(R),25(OH)2D3 causes RC cells to mature along the endochondral developmental pathway, where they become responsive to 1α,25(OH)2D3 and lose responsiveness to 24(R),25(OH)2D3, a characteristic of more mature growth zone (GC) chondrocytes. 1α,25(OH)2D3 elicits its effects on GC through different signal transduction pathways than those used by 24(R),25(OH)2D3 (PMID: 11179745 ). |
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Structure | [H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)CC[C@@H](O)C(C)(C)O InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22+,23-,24+,25-,27-/m1/s1 |
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Synonyms | Value | Source |
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(24R)-24,25-Dihydroxycholecalciferol | ChEBI | (24R)-24,25-Dihydroxyvitamin D3 | ChEBI | 24(R),25-Dihydroxyvitamin D3 | ChEBI | 24R,25(OH)2D3 | ChEBI | 24R,25-Dihydroxycholecalciferol | ChEBI | Secalciferol | ChEBI | Osteo D | Kegg | 24,25-Dihydroxycholecalciferol | HMDB | 24,25-Dihydroxyvitamin D3 | HMDB | Dihydroxyvitamin D3, 24,25 | HMDB | 24,25 Dihydroxyvitamin D 3 | HMDB | 24,25 Dihydroxyvitamin D3 | HMDB | 24,25-Dihydroxyvitamin D 3, (3beta,5Z,7E,24R)-isomer | HMDB | 24,25 Dihydroxycholecalciferol | HMDB | 24,25-Dihydroxyvitamin D 3 | HMDB | 24R,25 Dihydroxycholecalciferol | HMDB | (24R)-Hydroxycalcidiol | HMDB | (3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,24,25-triol | HMDB | (3Β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,24,25-triol | HMDB | 24(R),25-Dihydroxycholecalciferol | HMDB | 24,25-Dihydroxyvitamin D | HMDB | 24-Hydroxycalcidiol | HMDB | 24(R),25(OH)2D3 | HMDB | 24R,25-Dihydroxyvitamin D3 | ChEBI |
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Chemical Formula | C27H44O3 |
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Average Molecular Weight | 416.646 |
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Monoisotopic Molecular Weight | 416.329045277 |
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IUPAC Name | (3R,6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol |
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Traditional Name | secalciferol |
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CAS Registry Number | 55721-11-4 |
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SMILES | [H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)CC[C@@H](O)C(C)(C)O |
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InChI Identifier | InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22+,23-,24+,25-,27-/m1/s1 |
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InChI Key | FCKJYANJHNLEEP-XRWYNYHCSA-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 | Not Available |
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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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24R,25-Dihydroxyvitamin D3,1TMS,isomer #1 | C=C1CC[C@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O)C(C)(C)O | 3434.0 | Semi standard non polar | 33892256 | 24R,25-Dihydroxyvitamin D3,1TMS,isomer #2 | C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O[Si](C)(C)C)C(C)(C)O | 3482.0 | Semi standard non polar | 33892256 | 24R,25-Dihydroxyvitamin D3,1TMS,isomer #3 | C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O)C(C)(C)O[Si](C)(C)C | 3515.6 | Semi standard non polar | 33892256 | 24R,25-Dihydroxyvitamin D3,2TMS,isomer #1 | C=C1CC[C@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O[Si](C)(C)C)C(C)(C)O | 3435.4 | Semi standard non polar | 33892256 | 24R,25-Dihydroxyvitamin D3,2TMS,isomer #2 | C=C1CC[C@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O)C(C)(C)O[Si](C)(C)C | 3486.0 | Semi standard non polar | 33892256 | 24R,25-Dihydroxyvitamin D3,2TMS,isomer #3 | C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O[Si](C)(C)C)C(C)(C)O[Si](C)(C)C | 3532.1 | Semi standard non polar | 33892256 | 24R,25-Dihydroxyvitamin D3,3TMS,isomer #1 | C=C1CC[C@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O[Si](C)(C)C)C(C)(C)O[Si](C)(C)C | 3503.3 | Semi standard non polar | 33892256 | 24R,25-Dihydroxyvitamin D3,1TBDMS,isomer #1 | C=C1CC[C@H](O[Si](C)(C)C(C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O)C(C)(C)O | 3629.6 | Semi standard non polar | 33892256 | 24R,25-Dihydroxyvitamin D3,1TBDMS,isomer #2 | C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C(C)(C)O | 3709.8 | Semi standard non polar | 33892256 | 24R,25-Dihydroxyvitamin D3,1TBDMS,isomer #3 | C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O)C(C)(C)O[Si](C)(C)C(C)(C)C | 3741.1 | Semi standard non polar | 33892256 | 24R,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)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C(C)(C)O | 3877.9 | Semi standard non polar | 33892256 | 24R,25-Dihydroxyvitamin D3,2TBDMS,isomer #2 | C=C1CC[C@H](O[Si](C)(C)C(C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O)C(C)(C)O[Si](C)(C)C(C)(C)C | 3927.1 | Semi standard non polar | 33892256 | 24R,25-Dihydroxyvitamin D3,2TBDMS,isomer #3 | C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C(C)(C)O[Si](C)(C)C(C)(C)C | 3984.1 | Semi standard non polar | 33892256 | 24R,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)[C@H]1CC[C@@H]2[C@H](C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C(C)(C)O[Si](C)(C)C(C)(C)C | 4180.7 | 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 - 24R,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 - 24R,25-Dihydroxyvitamin D3 10V, Positive-QTOF | splash10-00l2-0119200000-9408ca86b83bf63d853f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 24R,25-Dihydroxyvitamin D3 20V, Positive-QTOF | splash10-0a5a-1469100000-15967532fe6b0b27c09c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 24R,25-Dihydroxyvitamin D3 40V, Positive-QTOF | splash10-0zmi-6396100000-3000f5727d0dad4b2351 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 24R,25-Dihydroxyvitamin D3 10V, Negative-QTOF | splash10-014i-0005900000-c4be780e228f40b4d0fb | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 24R,25-Dihydroxyvitamin D3 20V, Negative-QTOF | splash10-066s-1009300000-fd3202f74d1a84dfae95 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 24R,25-Dihydroxyvitamin D3 40V, Negative-QTOF | splash10-0079-9005000000-fa0288a9145c4ccb232e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 24R,25-Dihydroxyvitamin D3 10V, Positive-QTOF | splash10-00m0-0339300000-e33d06b378a97923b97d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 24R,25-Dihydroxyvitamin D3 20V, Positive-QTOF | splash10-0kml-6494000000-48fa9e19701bee349527 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 24R,25-Dihydroxyvitamin D3 40V, Positive-QTOF | splash10-066u-4961000000-5fb8b17537725cdef3c8 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 24R,25-Dihydroxyvitamin D3 10V, Negative-QTOF | splash10-014j-0006900000-7d1124e362f13b9eb696 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 24R,25-Dihydroxyvitamin D3 20V, Negative-QTOF | splash10-0670-1009400000-968d45c08ce476c37406 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 24R,25-Dihydroxyvitamin D3 40V, Negative-QTOF | splash10-08fr-4623900000-daa2c5a17d980b09964f | 2021-09-24 | Wishart Lab | View Spectrum |
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