Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-12 02:40:30 UTC |
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Update Date | 2022-03-07 02:56:51 UTC |
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HMDB ID | HMDB0041037 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 8-Deoxy-11-hydroxy-13-chlorogrosheimin |
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Description | 8-Deoxy-11-hydroxy-13-chlorogrosheimin belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Based on a literature review a small amount of articles have been published on 8-Deoxy-11-hydroxy-13-chlorogrosheimin. |
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Structure | CC1C2C(CC1=O)C(=C)CCC1C2OC(=O)C1(O)CCl InChI=1S/C15H19ClO4/c1-7-3-4-10-13(20-14(18)15(10,19)6-16)12-8(2)11(17)5-9(7)12/h8-10,12-13,19H,1,3-6H2,2H3 |
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Synonyms | Not Available |
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Chemical Formula | C15H19ClO4 |
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Average Molecular Weight | 298.762 |
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Monoisotopic Molecular Weight | 298.097186803 |
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IUPAC Name | 3-(chloromethyl)-3-hydroxy-9-methyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione |
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Traditional Name | 3-(chloromethyl)-3-hydroxy-9-methyl-6-methylidene-octahydroazuleno[4,5-b]furan-2,8-dione |
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CAS Registry Number | 83551-02-4 |
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SMILES | CC1C2C(CC1=O)C(=C)CCC1C2OC(=O)C1(O)CCl |
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InChI Identifier | InChI=1S/C15H19ClO4/c1-7-3-4-10-13(20-14(18)15(10,19)6-16)12-8(2)11(17)5-9(7)12/h8-10,12-13,19H,1,3-6H2,2H3 |
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InChI Key | RXUIKPFKVDKIDO-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. |
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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 | Terpene lactones |
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Direct Parent | Guaianolides and derivatives |
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Alternative Parents | |
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Substituents | - Guaianolide-skeleton
- Guaiane sesquiterpenoid
- Sesquiterpenoid
- Gamma butyrolactone
- Tertiary alcohol
- Tetrahydrofuran
- Carboxylic acid ester
- Chlorohydrin
- Halohydrin
- Ketone
- Lactone
- Cyclic ketone
- Monocarboxylic acid or derivatives
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Carbonyl group
- Alkyl halide
- Alkyl chloride
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Organohalogen compound
- Organochloride
- Organooxygen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic 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 | |
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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 | 228 - 230 °C | 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 | |
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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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8-Deoxy-11-hydroxy-13-chlorogrosheimin,1TMS,isomer #1 | C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C)C2C(C)C(=O)CC12 | 2345.8 | Semi standard non polar | 33892256 | 8-Deoxy-11-hydroxy-13-chlorogrosheimin,1TMS,isomer #2 | C=C1CCC2C(OC(=O)C2(O)CCl)C2C(C)=C(O[Si](C)(C)C)CC12 | 2344.3 | Semi standard non polar | 33892256 | 8-Deoxy-11-hydroxy-13-chlorogrosheimin,1TMS,isomer #3 | C=C1CCC2C(OC(=O)C2(O)CCl)C2C(C)C(O[Si](C)(C)C)=CC12 | 2266.7 | Semi standard non polar | 33892256 | 8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TMS,isomer #1 | C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C)C2C(C)=C(O[Si](C)(C)C)CC12 | 2439.4 | Semi standard non polar | 33892256 | 8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TMS,isomer #1 | C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C)C2C(C)=C(O[Si](C)(C)C)CC12 | 2317.4 | Standard non polar | 33892256 | 8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TMS,isomer #2 | C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C)C2C(C)C(O[Si](C)(C)C)=CC12 | 2353.2 | Semi standard non polar | 33892256 | 8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TMS,isomer #2 | C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C)C2C(C)C(O[Si](C)(C)C)=CC12 | 2275.2 | Standard non polar | 33892256 | 8-Deoxy-11-hydroxy-13-chlorogrosheimin,1TBDMS,isomer #1 | C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C(C)(C)C)C2C(C)C(=O)CC12 | 2582.0 | Semi standard non polar | 33892256 | 8-Deoxy-11-hydroxy-13-chlorogrosheimin,1TBDMS,isomer #2 | C=C1CCC2C(OC(=O)C2(O)CCl)C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC12 | 2560.3 | Semi standard non polar | 33892256 | 8-Deoxy-11-hydroxy-13-chlorogrosheimin,1TBDMS,isomer #3 | C=C1CCC2C(OC(=O)C2(O)CCl)C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC12 | 2494.6 | Semi standard non polar | 33892256 | 8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TBDMS,isomer #1 | C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C(C)(C)C)C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC12 | 2891.9 | Semi standard non polar | 33892256 | 8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TBDMS,isomer #1 | C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C(C)(C)C)C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC12 | 2771.8 | Standard non polar | 33892256 | 8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TBDMS,isomer #2 | C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C(C)(C)C)C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC12 | 2815.1 | Semi standard non polar | 33892256 | 8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TBDMS,isomer #2 | C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C(C)(C)C)C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC12 | 2633.9 | Standard non polar | 33892256 |
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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 - 8-Deoxy-11-hydroxy-13-chlorogrosheimin GC-MS (Non-derivatized) - 70eV, Positive | splash10-008c-2920000000-44ae0b69be8d75a2a187 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin GC-MS (1 TMS) - 70eV, Positive | splash10-004i-4902000000-50f17b549f2e6e7f90b4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 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 - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 10V, Positive-QTOF | splash10-002b-0890000000-40f6f688c2acce1d1184 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 20V, Positive-QTOF | splash10-009t-0390000000-08991e47ab6812ec5ab4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 40V, Positive-QTOF | splash10-014i-5900000000-8b89b2cc6d7b62e09711 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 10V, Negative-QTOF | splash10-0002-0090000000-47a20af26bd64262e0c1 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 20V, Negative-QTOF | splash10-0002-0090000000-e826cd39455497d2dccd | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 40V, Negative-QTOF | splash10-03xr-3900000000-7666c2778dae979efc5c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 10V, Positive-QTOF | splash10-0002-0090000000-714a78dc20d5d6ba33e8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 20V, Positive-QTOF | splash10-000t-0090000000-570bd856dcf23ec3ece3 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 40V, Positive-QTOF | splash10-05di-2930000000-92a37ea277bcf8d701f9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 10V, Negative-QTOF | splash10-0002-0090000000-86aef986368eb478dde3 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 20V, Negative-QTOF | splash10-0002-1090000000-c3e577c87e0a2ce70497 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 40V, Negative-QTOF | splash10-001l-4290000000-d45be43cfe8adaedd5c9 | 2021-09-25 | Wishart Lab | View 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 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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