Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2020-02-26 21:41:51 UTC |
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HMDB ID | HMDB0015567 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Calcipotriol |
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Description | Calcipotriol is only found in individuals that have used or taken this drug. It is a synthetic derivative of calcitriol or Vitamin D.The precise mechanism of calcipotriol in remitting psoriasis is not well-understood. However, it has been shown to have comparable affinity with calcitriol for the Vitamin D receptor, while being less than 1% as active as the calcitriol in regulating calcium metabolism. The Vitamin D receptor (VDR) belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kindney, and T cells of the immune system. T cells are known to play a role in psoriasis, and it is thought that the binding of calcipotriol to the VDR modulates the T cells gene transcription of cell differentiation and proliferation related genes. |
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Structure | |
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Synonyms | Value | Source |
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Calcipotriene | ChEBI | Daivonex | ChEBI | Dovonex | ChEBI | Bristol-myers squibb brand OF calcipotriene | HMDB | Psorcutan | HMDB | 1,24(OH)2-22-Ene-24-cyclopropyl D3 | HMDB | Leo brand OF calcipotriene | HMDB | Schering brand OF calcipotriene | HMDB | CSL Brand OF calcipotriene | HMDB | Senosiain brand OF calcipotriene | HMDB | Sorilux | HMDB | Farmacusi brand OF calcipotriene | HMDB | Heximar win care | HMDB | Calcipotriol | KEGG | (22E)-(24S)-1a,24-Dihydroxy-26,27-cyclo-22,23-didehydrovitamin D3 / (22E)-(24S)-1a,24-dihydroxy-26,27-cyclo-22,23-didehydrocholecalciferol / calcipotriol | Generator | (22E)-(24S)-1Α,24-dihydroxy-26,27-cyclo-22,23-didehydrovitamin D3 / (22E)-(24S)-1α,24-dihydroxy-26,27-cyclo-22,23-didehydrocholecalciferol / calcipotriol | Generator | Enstilar | MeSH |
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Chemical Formula | C27H40O3 |
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Average Molecular Weight | 412.6047 |
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Monoisotopic Molecular Weight | 412.297745146 |
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IUPAC Name | (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol |
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Traditional Name | calcipotriol |
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CAS Registry Number | 112965-21-6 |
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SMILES | O[C@H](\C=C\[C@@H](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)C1CC1 |
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InChI Identifier | InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1 |
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InChI Key | LWQQLNNNIPYSNX-UROSTWAQSA-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
- 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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Disposition | Source: Route of exposure: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.014 g/L | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00kg-2019000000-25fe74385dfaaadc4f64 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-03di-2200159000-60ddca8d21526e4244de | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002b-0019100000-dd8b67e911e2c011a451 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00fr-3349000000-721114fcaf3ed169df5d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fki-9568000000-c7e61ad61191fce88abe | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0006900000-01ce5bd91cb0ca4dcbec | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ox-2009300000-7f4afaeab87ae0e61d8d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9005000000-075615c00f3c0728d5ed | Spectrum |
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General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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