Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 18:21:12 UTC |
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Update Date | 2022-03-07 02:53:47 UTC |
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HMDB ID | HMDB0033606 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Artemoin C |
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Description | Artemoin C belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Based on a literature review a small amount of articles have been published on Artemoin C. |
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Structure | CCCCCCCCCCCCCCC(O)C(O)CCCCCCCCCCCCCCC1=CC(C)OC1=O InChI=1S/C35H66O4/c1-3-4-5-6-7-8-9-13-16-19-22-25-28-33(36)34(37)29-26-23-20-17-14-11-10-12-15-18-21-24-27-32-30-31(2)39-35(32)38/h30-31,33-34,36-37H,3-29H2,1-2H3 |
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Synonyms | Value | Source |
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3-(15,16-Dihydroxytriacontyl)-5-methyl-2(5H)-furanone | ChEBI |
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Chemical Formula | C35H66O4 |
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Average Molecular Weight | 550.8961 |
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Monoisotopic Molecular Weight | 550.4961106 |
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IUPAC Name | 3-(15,16-dihydroxytriacontyl)-5-methyl-2,5-dihydrofuran-2-one |
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Traditional Name | 3-(15,16-dihydroxytriacontyl)-5-methyl-5H-furan-2-one |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCCCCCC(O)C(O)CCCCCCCCCCCCCCC1=CC(C)OC1=O |
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InChI Identifier | InChI=1S/C35H66O4/c1-3-4-5-6-7-8-9-13-16-19-22-25-28-33(36)34(37)29-26-23-20-17-14-11-10-12-15-18-21-24-27-32-30-31(2)39-35(32)38/h30-31,33-34,36-37H,3-29H2,1-2H3 |
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InChI Key | MBDVKGSWKNHBQZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. |
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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 | Fatty alcohols |
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Direct Parent | Annonaceous acetogenins |
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Alternative Parents | |
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Substituents | - Annonaceae acetogenin skeleton
- Long chain fatty alcohol
- 2-furanone
- Dihydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Lactone
- 1,2-diol
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organoheterocyclic compound
- Oxacycle
- Alcohol
- Organooxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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 | 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 | |
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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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Artemoin C,1TMS,isomer #1 | CCCCCCCCCCCCCCC(O[Si](C)(C)C)C(O)CCCCCCCCCCCCCCC1=CC(C)OC1=O | 4187.4 | Semi standard non polar | 33892256 | Artemoin C,1TMS,isomer #2 | CCCCCCCCCCCCCCC(O)C(CCCCCCCCCCCCCCC1=CC(C)OC1=O)O[Si](C)(C)C | 4187.4 | Semi standard non polar | 33892256 | Artemoin C,2TMS,isomer #1 | CCCCCCCCCCCCCCC(O[Si](C)(C)C)C(CCCCCCCCCCCCCCC1=CC(C)OC1=O)O[Si](C)(C)C | 4118.9 | Semi standard non polar | 33892256 | Artemoin C,1TBDMS,isomer #1 | CCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(O)CCCCCCCCCCCCCCC1=CC(C)OC1=O | 4444.9 | Semi standard non polar | 33892256 | Artemoin C,1TBDMS,isomer #2 | CCCCCCCCCCCCCCC(O)C(CCCCCCCCCCCCCCC1=CC(C)OC1=O)O[Si](C)(C)C(C)(C)C | 4444.8 | Semi standard non polar | 33892256 | Artemoin C,2TBDMS,isomer #1 | CCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(CCCCCCCCCCCCCCC1=CC(C)OC1=O)O[Si](C)(C)C(C)(C)C | 4626.5 | Semi 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 - Artemoin C GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-4394110000-5db1a8084c298f2dc7fe | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin C GC-MS (2 TMS) - 70eV, Positive | splash10-0f92-8723908000-29af7ad8f8730c212328 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin C GC-MS ("Artemoin C,1TMS,#1" TMS) - 70eV, Positive | Not Available | 2021-10-14 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin C GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin C GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin C GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin C GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Artemoin C GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-10-15 | 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 - Artemoin C 10V, Positive-QTOF | splash10-0udi-0000190000-474aaada1ba26a9060c9 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin C 20V, Positive-QTOF | splash10-0005-3941240000-ae345e3e476c7dde163e | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin C 40V, Positive-QTOF | splash10-0a4m-5960200000-b0617e00161948441cdf | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin C 10V, Negative-QTOF | splash10-0002-0000090000-6f02dd1783a193decbcf | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin C 20V, Negative-QTOF | splash10-052b-1173090000-60d6de7c29d5351b53d3 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin C 40V, Negative-QTOF | splash10-0a4i-2093010000-2745c89ffd98f04db4e2 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin C 10V, Positive-QTOF | splash10-0159-1011190000-e499d2c40d7391a95222 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin C 20V, Positive-QTOF | splash10-0f89-2000190000-92f8104e8c5535d3bfa8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin C 40V, Positive-QTOF | splash10-052f-9101100000-d0c94abf0c377eb4bcfe | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin C 10V, Negative-QTOF | splash10-0002-0003090000-6fd15fecca2722ef289c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin C 20V, Negative-QTOF | splash10-0002-2043090000-3615e929b4bcb20bd413 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Artemoin C 40V, Negative-QTOF | splash10-05fr-5339010000-02a2895d13983d7402ea | 2021-09-22 | 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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