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 02:52:00 UTC |
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HMDB ID | HMDB0015504 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Alfacalcidol |
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Description | Alfacalcidol is an active metabolite of Vitamin D, which performs important functions in regulation of the calcium balance and the bone metabolism. Alfacalcidol is Vitamin D-hormone analog which is activated by the enzyme 25-hydroxylase in the liver for systemic and in osteoblasts for local D-hormone actions. It possesses a unique pattern of pleiotropic effects on, e.g. gut, bone, pararthyroids, muscle and brain. Alfacalcidol is superior to plain vitamin D (cholecalciferol) because the final kidney activation of the latter is regulated by a negative feedback mechanism. (PMID:17438884 ,17668216 ). |
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Structure | CC(C)CCC[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 InChI=1S/C27H44O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h11-12,18-19,23-26,28-29H,4,6-10,13-17H2,1-3,5H3/b21-11+,22-12-/t19-,23-,24-,25+,26+,27-/m1/s1 |
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Synonyms | Value | Source |
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(5Z,7E)-9,10-Seco-5,7,10(19)-cholestatrien-1alpha,3beta-diol | ChEBI | 1alpha-Hydroxy-vitamin D3 | ChEBI | 1alpha-Hydroxycholecalciferol | ChEBI | 1alpha-Hydroxyvitamin D3 | ChEBI | 9,10-Secocholesta-5,7,10(19)-triene-1alpha,3beta-diol | ChEBI | Alfacalcidolum | ChEBI | Alsiodol | ChEBI | (5Z,7E)-9,10-Seco-5,7,10(19)-cholestatrien-1a,3b-diol | Generator | (5Z,7E)-9,10-Seco-5,7,10(19)-cholestatrien-1α,3β-diol | Generator | 1a-Hydroxy-vitamin D3 | Generator | 1Α-hydroxy-vitamin D3 | Generator | 1a-Hydroxycholecalciferol | Generator | 1Α-hydroxycholecalciferol | Generator | 1a-Hydroxyvitamin D3 | Generator | 1Α-hydroxyvitamin D3 | Generator | 9,10-Secocholesta-5,7,10(19)-triene-1a,3b-diol | Generator | 9,10-Secocholesta-5,7,10(19)-triene-1α,3β-diol | Generator | 1-Hydroxycholecalciferol | HMDB | 1 alpha-Hydroxycholecalciferol | HMDB | 1-alpha-Oxycholecalciferol | HMDB | 1-Hydroxycholecalciferol, (1alpha,3alpha-(5Z,7E))-isomer | HMDB | 1-Hydroxycholecalciferol, (1beta)-(5Z)-isomer | HMDB | 1alpha-OHD3 | HMDB | AlfaD | HMDB | Oksidevit | HMDB | Un-alfa | HMDB | 1 alpha-Hydroxyvitamin D3 | HMDB | 1-Hydroxycholecalciferol, (1beta,3beta-(5E,7E))-isomer | HMDB | Bondiol | HMDB | Doss brand OF alfacalcidol | HMDB | Alphacalcidol | HMDB | 1-Hydroxycholecalciferol, aluminum salt | HMDB | EinsAlpha | HMDB | Etalpha | HMDB | Eenalfadrie | HMDB | One-Alpha | HMDB | 1a-Hydroxyvitamin D3 / 1a-hydroxycholecalciferol | HMDB | 1Α-hydroxyvitamin D3 / 1α-hydroxycholecalciferol | HMDB | Alfacalcidol | MeSH |
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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,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol |
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Traditional Name | etα |
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CAS Registry Number | 41294-56-8 |
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SMILES | CC(C)CCC[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 |
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InChI Identifier | InChI=1S/C27H44O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h11-12,18-19,23-26,28-29H,4,6-10,13-17H2,1-3,5H3/b21-11+,22-12-/t19-,23-,24-,25+,26+,27-/m1/s1 |
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InChI Key | OFHCOWSQAMBJIW-AVJTYSNKSA-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 | 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 | 136 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0016 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 | | 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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Alfacalcidol,1TMS,isomer #1 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O | 3242.9 | Semi standard non polar | 33892256 | Alfacalcidol,1TMS,isomer #2 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C | 3233.6 | Semi standard non polar | 33892256 | Alfacalcidol,2TMS,isomer #1 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C | 3181.8 | Semi standard non polar | 33892256 | Alfacalcidol,1TBDMS,isomer #1 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O | 3467.4 | Semi standard non polar | 33892256 | Alfacalcidol,1TBDMS,isomer #2 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3446.7 | Semi standard non polar | 33892256 | Alfacalcidol,2TBDMS,isomer #1 | C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C | 3613.6 | 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 - Alfacalcidol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a5l-1019000000-4bbe28a5b3bcf0e3f286 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Alfacalcidol GC-MS (2 TMS) - 70eV, Positive | splash10-004i-7101590000-c90de60556296aeee67c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Alfacalcidol 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 - Alfacalcidol 10V, Positive-QTOF | splash10-0f89-0129200000-ce55736fb60be5e0024f | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alfacalcidol 20V, Positive-QTOF | splash10-00e9-2496000000-6be131b12013c8feea5c | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alfacalcidol 40V, Positive-QTOF | splash10-074j-6395000000-2c39ba62f7c36fc0a44a | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alfacalcidol 10V, Negative-QTOF | splash10-0002-0009000000-cdef64e29d5e6355c8fe | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alfacalcidol 20V, Negative-QTOF | splash10-000t-0009000000-a22d1c4bcbcd6fbeaf2c | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alfacalcidol 40V, Negative-QTOF | splash10-001i-1129000000-91782a773e5f99cf3270 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alfacalcidol 10V, Positive-QTOF | splash10-0ue9-0379600000-d676c4ba59a242f28062 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alfacalcidol 20V, Positive-QTOF | splash10-00rm-4298100000-c624703a1882c35b8975 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alfacalcidol 40V, Positive-QTOF | splash10-03ka-5931000000-5fa16451ff2ca2eab28c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alfacalcidol 10V, Negative-QTOF | splash10-0002-0009000000-dc23ba87137530d83f68 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alfacalcidol 20V, Negative-QTOF | splash10-0002-0309000000-c5c00960affa6353a810 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Alfacalcidol 40V, Negative-QTOF | splash10-002b-0629000000-2b1b864f66e3930d49a0 | 2021-10-11 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01436 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01436 | | details |
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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 | DB01436 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4445376 |
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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 | Alfacalcidol |
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METLIN ID | Not Available |
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PubChem Compound | 5282181 |
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PDB ID | Not Available |
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ChEBI ID | 31186 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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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 | - Galesanu C, Ciubotariu C, Melnic G, Galesanu MR: [Postmenopausal osteoporosis. Digital Rx radiogrammetry in the diagnosis and follow-up of treatment with alfacalcidol]. Rev Med Chir Soc Med Nat Iasi. 2006 Oct-Dec;110(4):833-41. [PubMed:17438884 ]
- Ringe JD, Schacht E: Improving the outcome of established therapies for osteoporosis by adding the active D-hormone analog alfacalcidol. Rheumatol Int. 2007 Dec;28(2):103-11. Epub 2007 Aug 1. [PubMed:17668216 ]
- 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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