Record Information |
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Version | 5.0 |
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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 | 2022-03-07 02:52:02 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 | 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 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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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 | (22E)-(24S)-1a,24-Dihydroxy-26,27-cyclo-22,23-didehydrovitamin D3 / (22E)-(24S)-1a,24-dihydroxy-26,27-cyclo-22,23-didehydrocholecalciferol / calcipotriol | HMDB | (22E)-(24S)-1Α,24-dihydroxy-26,27-cyclo-22,23-didehydrovitamin D3 / (22E)-(24S)-1α,24-dihydroxy-26,27-cyclo-22,23-didehydrocholecalciferol / calcipotriol | HMDB | Enstilar | HMDB | Calcipotriol | KEGG |
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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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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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 | 0.014 g/L | 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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Calcipotriol,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@@H](O[Si](C)(C)C)C2CC2)C[C@@H](O)C[C@@H]1O | 3575.0 | Semi standard non polar | 33892256 | Calcipotriol,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@@H](O)C2CC2)C[C@@H](O[Si](C)(C)C)C[C@@H]1O | 3558.0 | Semi standard non polar | 33892256 | Calcipotriol,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@@H](O)C2CC2)C[C@@H](O)C[C@@H]1O[Si](C)(C)C | 3568.1 | Semi standard non polar | 33892256 | Calcipotriol,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@@H](O[Si](C)(C)C)C2CC2)C[C@@H](O[Si](C)(C)C)C[C@@H]1O | 3507.0 | Semi standard non polar | 33892256 | Calcipotriol,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@@H](O[Si](C)(C)C)C2CC2)C[C@@H](O)C[C@@H]1O[Si](C)(C)C | 3504.2 | Semi standard non polar | 33892256 | Calcipotriol,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@@H](O)C2CC2)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C | 3487.0 | Semi standard non polar | 33892256 | Calcipotriol,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@@H](O[Si](C)(C)C)C2CC2)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C | 3439.5 | Semi standard non polar | 33892256 | Calcipotriol,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@@H](O[Si](C)(C)C(C)(C)C)C2CC2)C[C@@H](O)C[C@@H]1O | 3806.0 | Semi standard non polar | 33892256 | Calcipotriol,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@@H](O)C2CC2)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O | 3776.8 | Semi standard non polar | 33892256 | Calcipotriol,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@@H](O)C2CC2)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3773.9 | Semi standard non polar | 33892256 | Calcipotriol,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@@H](O[Si](C)(C)C(C)(C)C)C2CC2)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O | 3960.1 | Semi standard non polar | 33892256 | Calcipotriol,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@@H](O[Si](C)(C)C(C)(C)C)C2CC2)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3933.4 | Semi standard non polar | 33892256 | Calcipotriol,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@@H](O)C2CC2)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3922.1 | Semi standard non polar | 33892256 | Calcipotriol,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@@H](O[Si](C)(C)C(C)(C)C)C2CC2)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C | 4073.2 | Semi standard non polar | 33892256 |
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