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 15:01:37 UTC |
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Update Date | 2021-09-14 15:39:00 UTC |
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HMDB ID | HMDB0014256 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Tafluprost free acid |
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Description | Tafluprost free acid belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Based on a literature review a small amount of articles have been published on Tafluprost free acid. |
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Structure | OC1CC(O)C(\C=C\C(F)(F)COC2=CC=CC=C2)C1C\C=C/CCCC(O)=O InChI=1S/C22H28F2O5/c23-22(24,15-29-16-8-4-3-5-9-16)13-12-18-17(19(25)14-20(18)26)10-6-1-2-7-11-21(27)28/h1,3-6,8-9,12-13,17-20,25-26H,2,7,10-11,14-15H2,(H,27,28)/b6-1-,13-12+ |
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Synonyms | Value | Source |
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(5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoate | HMDB |
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Chemical Formula | C22H28F2O5 |
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Average Molecular Weight | 410.4515 |
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Monoisotopic Molecular Weight | 410.190480416 |
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IUPAC Name | (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoic acid |
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Traditional Name | (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoic acid |
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CAS Registry Number | Not Available |
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SMILES | OC1CC(O)C(\C=C\C(F)(F)COC2=CC=CC=C2)C1C\C=C/CCCC(O)=O |
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InChI Identifier | InChI=1S/C22H28F2O5/c23-22(24,15-29-16-8-4-3-5-9-16)13-12-18-17(19(25)14-20(18)26)10-6-1-2-7-11-21(27)28/h1,3-6,8-9,12-13,17-20,25-26H,2,7,10-11,14-15H2,(H,27,28)/b6-1-,13-12+ |
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InChI Key | KIQXRQVVYTYYAZ-MTNCBHNASA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Eicosanoids |
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Direct Parent | Prostaglandins and related compounds |
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Alternative Parents | |
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Substituents | - Prostaglandin skeleton
- Long-chain fatty acid
- Phenoxy compound
- Phenol ether
- Alkyl aryl ether
- Halogenated fatty acid
- Hydroxy fatty acid
- Monocyclic benzene moiety
- Fatty acid
- Benzenoid
- Unsaturated fatty acid
- Cyclopentanol
- Cyclic alcohol
- Secondary alcohol
- Ether
- Carboxylic acid
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Organohalogen compound
- Organofluoride
- Organooxygen compound
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Alkyl halide
- Alkyl fluoride
- Organic oxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | Not Available |
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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 | | 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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Tafluprost free acid,1TMS,isomer #1 | C[Si](C)(C)OC1CC(O)C(/C=C/C(F)(F)COC2=CC=CC=C2)C1C/C=C\CCCC(=O)O | 2946.5 | Semi standard non polar | 33892256 | Tafluprost free acid,1TMS,isomer #2 | C[Si](C)(C)OC1CC(O)C(C/C=C\CCCC(=O)O)C1/C=C/C(F)(F)COC1=CC=CC=C1 | 2938.1 | Semi standard non polar | 33892256 | Tafluprost free acid,1TMS,isomer #3 | C[Si](C)(C)OC(=O)CCC/C=C\CC1C(O)CC(O)C1/C=C/C(F)(F)COC1=CC=CC=C1 | 2939.9 | Semi standard non polar | 33892256 | Tafluprost free acid,2TMS,isomer #1 | C[Si](C)(C)OC1CC(O[Si](C)(C)C)C(C/C=C\CCCC(=O)O)C1/C=C/C(F)(F)COC1=CC=CC=C1 | 2921.5 | Semi standard non polar | 33892256 | Tafluprost free acid,2TMS,isomer #2 | C[Si](C)(C)OC(=O)CCC/C=C\CC1C(O[Si](C)(C)C)CC(O)C1/C=C/C(F)(F)COC1=CC=CC=C1 | 2888.1 | Semi standard non polar | 33892256 | Tafluprost free acid,2TMS,isomer #3 | C[Si](C)(C)OC(=O)CCC/C=C\CC1C(O)CC(O[Si](C)(C)C)C1/C=C/C(F)(F)COC1=CC=CC=C1 | 2879.4 | Semi standard non polar | 33892256 | Tafluprost free acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)CCC/C=C\CC1C(O[Si](C)(C)C)CC(O[Si](C)(C)C)C1/C=C/C(F)(F)COC1=CC=CC=C1 | 2837.7 | Semi standard non polar | 33892256 | Tafluprost free acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1CC(O)C(/C=C/C(F)(F)COC2=CC=CC=C2)C1C/C=C\CCCC(=O)O | 3181.3 | Semi standard non polar | 33892256 | Tafluprost free acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1CC(O)C(C/C=C\CCCC(=O)O)C1/C=C/C(F)(F)COC1=CC=CC=C1 | 3169.3 | Semi standard non polar | 33892256 | Tafluprost free acid,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC1C(O)CC(O)C1/C=C/C(F)(F)COC1=CC=CC=C1 | 3197.2 | Semi standard non polar | 33892256 | Tafluprost free acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1CC(O[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O)C1/C=C/C(F)(F)COC1=CC=CC=C1 | 3339.4 | Semi standard non polar | 33892256 | Tafluprost free acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC1C(O[Si](C)(C)C(C)(C)C)CC(O)C1/C=C/C(F)(F)COC1=CC=CC=C1 | 3339.8 | Semi standard non polar | 33892256 | Tafluprost free acid,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC1C(O)CC(O[Si](C)(C)C(C)(C)C)C1/C=C/C(F)(F)COC1=CC=CC=C1 | 3332.9 | Semi standard non polar | 33892256 | Tafluprost free acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\CC1C(O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C1/C=C/C(F)(F)COC1=CC=CC=C1 | 3470.7 | 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 - Tafluprost free acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-014r-1219000000-8e1ec65ae01361e172d1 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Tafluprost free acid GC-MS (3 TMS) - 70eV, Positive | splash10-03di-5500489000-95bafbabe02fb2fdaf57 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Tafluprost free acid 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 - Tafluprost free acid 10V, Positive-QTOF | splash10-002g-1029100000-204ed18144108c4fbbb2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tafluprost free acid 20V, Positive-QTOF | splash10-002e-1229000000-25077f9e4ce508bf95e3 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tafluprost free acid 40V, Positive-QTOF | splash10-000b-9260000000-076c2111abf02e5ae67b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tafluprost free acid 10V, Negative-QTOF | splash10-0006-9002200000-c00792117fdb4db5e3ef | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tafluprost free acid 20V, Negative-QTOF | splash10-0006-9001000000-08fd3ce154d6769f5222 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tafluprost free acid 40V, Negative-QTOF | splash10-0006-9110000000-0e95f48713dae3d60241 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tafluprost free acid 10V, Negative-QTOF | splash10-0006-9001300000-7aec5b4ddcff3ac3f0c2 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tafluprost free acid 20V, Negative-QTOF | splash10-0006-9000000000-08485aaf085c13d5129a | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tafluprost free acid 40V, Negative-QTOF | splash10-0006-9000000000-08485aaf085c13d5129a | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tafluprost free acid 10V, Positive-QTOF | splash10-004l-0049100000-6ef9a55a21ae3bd86e51 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tafluprost free acid 20V, Positive-QTOF | splash10-00nr-2289000000-5abc56977aad023ef4d0 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tafluprost free acid 40V, Positive-QTOF | splash10-00pu-9232000000-28994a5f3f961fcc7dbc | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | |
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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 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry | | 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 | Not Available |
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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 | 21467507 |
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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 | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 131750728 |
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PDB ID | Not Available |
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ChEBI ID | 176015 |
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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 | - 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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