Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-06-16 13:14:51 UTC |
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Update Date | 2022-03-07 02:51:23 UTC |
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HMDB ID | HMDB0012329 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4-Oxoretinol |
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Description | 4-oxo-retinol, a metabolite of retinol synthesized in mouse embryonal carcinoma F9 cells,is active in inducing differentiation of these cells. It also functions as a ligand of retinoic acid receptors and a transcriptional activator of reporter. genes.[PMID: 9110564 ]. 4-Oxoretinol is a metabolite of retinol in the human promyelocytic leukemia cell line NB4 which induces cell growth arrest and granulocytic differentiation.[PMID: 9581846 ]. |
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Structure | C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C InChI=1S/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-12+ |
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Synonyms | Value | Source |
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4-Ketoretinol | ChEBI | 4-oxo-ROL | ChEBI | 3,7-Dimethyl-9-(3-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraen-1-ol | HMDB | 4-Ketovitamin a(1) | HMDB | 4-Ketovitamin-a-alcohol | HMDB | 4-Ketovitamin-alpha-alcohol | HMDB | 4-oxo-Retinol | HMDB | 4-OxoROL | HMDB | 4-Oxovitamin a1 | HMDB | 4-Oxovitamin-a-alcohol | HMDB | 4-Oxovitamin-alpha-alcohol | HMDB | 4OVA1 | HMDB | all-trans-4-Oxoretinol | HMDB, ChEBI | OXR | HMDB |
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Chemical Formula | C20H28O2 |
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Average Molecular Weight | 300.4351 |
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Monoisotopic Molecular Weight | 300.20893014 |
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IUPAC Name | 3-[(1E,3E,5E,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one |
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Traditional Name | 4-oxoretinol |
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CAS Registry Number | 62702-55-0 |
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SMILES | C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C |
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InChI Identifier | InChI=1S/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-12+ |
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InChI Key | PLIUCYCUYQIBDZ-RMWYGNQTSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Retinoids |
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Direct Parent | Retinoids |
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Alternative Parents | |
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Substituents | - Retinoid skeleton
- Diterpenoid
- Fatty alcohol
- Cyclohexenone
- Fatty acyl
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic 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 | |
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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 | 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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4-Oxoretinol,1TMS,isomer #1 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CCC1=O | 2742.7 | Semi standard non polar | 33892256 | 4-Oxoretinol,1TMS,isomer #2 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO)C(C)(C)CC=C1O[Si](C)(C)C | 2706.6 | Semi standard non polar | 33892256 | 4-Oxoretinol,2TMS,isomer #1 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C | 2771.7 | Semi standard non polar | 33892256 | 4-Oxoretinol,2TMS,isomer #1 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C | 2563.6 | Standard non polar | 33892256 | 4-Oxoretinol,2TMS,isomer #1 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C | 2709.7 | Standard polar | 33892256 | 4-Oxoretinol,1TBDMS,isomer #1 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CCC1=O | 2937.6 | Semi standard non polar | 33892256 | 4-Oxoretinol,1TBDMS,isomer #2 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C | 2917.7 | Semi standard non polar | 33892256 | 4-Oxoretinol,2TBDMS,isomer #1 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C | 3219.4 | Semi standard non polar | 33892256 | 4-Oxoretinol,2TBDMS,isomer #1 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C | 2956.5 | Standard non polar | 33892256 | 4-Oxoretinol,2TBDMS,isomer #1 | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C | 2911.5 | Standard 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 - 4-Oxoretinol GC-MS (Non-derivatized) - 70eV, Positive | splash10-000i-1290000000-4649d7f3ab4f61c01faf | 2017-08-28 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Oxoretinol GC-MS (1 TMS) - 70eV, Positive | splash10-0a4i-2129000000-ba7d9fd4931eaf6b6927 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Oxoretinol 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 - 4-Oxoretinol 10V, Positive-QTOF | splash10-0f89-0593000000-fac47a7263b1f70432a3 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Oxoretinol 20V, Positive-QTOF | splash10-0f7k-2960000000-e6ecb0d2ae19b738762b | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Oxoretinol 40V, Positive-QTOF | splash10-1000-8920000000-f526453f90130e118ba0 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Oxoretinol 10V, Negative-QTOF | splash10-0002-0090000000-c06dba726fc1a33b336f | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Oxoretinol 20V, Negative-QTOF | splash10-014j-0090000000-13c1ec01c1d802584537 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Oxoretinol 40V, Negative-QTOF | splash10-0frx-3490000000-ca40eaf3790e425d4408 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Oxoretinol 10V, Negative-QTOF | splash10-014i-0090000000-d04e40563394d4c84f5d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Oxoretinol 20V, Negative-QTOF | splash10-066s-0190000000-f4b17a8c6d2a8521525a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Oxoretinol 40V, Negative-QTOF | splash10-0udi-0590000000-35e8dfa966822e3e2574 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Oxoretinol 10V, Positive-QTOF | splash10-0fsr-0792000000-1526d46586ab5fe6ae7d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Oxoretinol 20V, Positive-QTOF | splash10-00lb-1930000000-c9e30f5fc51a908c8495 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Oxoretinol 40V, Positive-QTOF | splash10-002f-3900000000-eefd04e3e622ffcc6615 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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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 | DB02699 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB028948 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4451124 |
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KEGG Compound ID | C16683 |
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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 | 5289090 |
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PDB ID | OXR |
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ChEBI ID | 44597 |
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Food Biomarker Ontology | Not Available |
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VMH ID | M01032 |
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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 | - Ross SA, De Luca LM: A new metabolite of retinol: all-trans-4-oxo-retinol as a receptor activator and differentiation agent. Nutr Rev. 1996 Nov;54(11 Pt 1):355-6. [PubMed:9110564 ]
- Faria TN, Rivi R, Derguini F, Pandolfi PP, Gudas LJ: 4-Oxoretinol, a metabolite of retinol in the human promyelocytic leukemia cell line NB4, induces cell growth arrest and granulocytic differentiation. Cancer Res. 1998 May 1;58(9):2007-13. [PubMed:9581846 ]
- 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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