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 17:33:48 UTC |
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Update Date | 2022-03-07 02:52:22 UTC |
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HMDB ID | HMDB0029958 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Asitribin |
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Description | Asitribin 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 Asitribin. |
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Structure | CCCCCCC(O)CCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O InChI=1S/C37H66O7/c1-3-4-5-15-19-30(38)20-17-22-32(40)34-24-26-36(44-34)35-25-23-33(43-35)31(39)21-16-13-11-9-7-6-8-10-12-14-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3 |
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Synonyms | Not Available |
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Chemical Formula | C37H66O7 |
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Average Molecular Weight | 622.9157 |
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Monoisotopic Molecular Weight | 622.480854466 |
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IUPAC Name | 3-(13-{5-[5-(1,5-dihydroxyundecyl)oxolan-2-yl]oxolan-2-yl}-13-hydroxytridecyl)-5-methyl-2,5-dihydrofuran-2-one |
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Traditional Name | 3-(13-{5-[5-(1,5-dihydroxyundecyl)oxolan-2-yl]oxolan-2-yl}-13-hydroxytridecyl)-5-methyl-5H-furan-2-one |
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CAS Registry Number | 168113-64-2 |
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SMILES | CCCCCCC(O)CCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O |
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InChI Identifier | InChI=1S/C37H66O7/c1-3-4-5-15-19-30(38)20-17-22-32(40)34-24-26-36(44-34)35-25-23-33(43-35)31(39)21-16-13-11-9-7-6-8-10-12-14-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3 |
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InChI Key | DAEFUOXKPZLQMM-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
- Tetrahydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Organoheterocyclic compound
- Oxacycle
- Organooxygen compound
- Hydrocarbon derivative
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- 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 | 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 | 71 - 72 °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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Asitribin,1TMS,isomer #1 | CCCCCCC(CCCC(O)C1CCC(C2CCC(C(O)CCCCCCCCCCCCC3=CC(C)OC3=O)O2)O1)O[Si](C)(C)C | 4785.2 | Semi standard non polar | 33892256 | Asitribin,1TMS,isomer #2 | CCCCCCC(O)CCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(O)CCCCCCCCCCCCC3=CC(C)OC3=O)O2)O1 | 4766.7 | Semi standard non polar | 33892256 | Asitribin,1TMS,isomer #3 | CCCCCCC(O)CCCC(O)C1CCC(C2CCC(C(CCCCCCCCCCCCC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O1 | 4757.4 | Semi standard non polar | 33892256 | Asitribin,2TMS,isomer #1 | CCCCCCC(CCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(O)CCCCCCCCCCCCC3=CC(C)OC3=O)O2)O1)O[Si](C)(C)C | 4711.1 | Semi standard non polar | 33892256 | Asitribin,2TMS,isomer #2 | CCCCCCC(CCCC(O)C1CCC(C2CCC(C(CCCCCCCCCCCCC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O1)O[Si](C)(C)C | 4712.1 | Semi standard non polar | 33892256 | Asitribin,2TMS,isomer #3 | CCCCCCC(O)CCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(CCCCCCCCCCCCC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O1 | 4719.5 | Semi standard non polar | 33892256 | Asitribin,3TMS,isomer #1 | CCCCCCC(CCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(CCCCCCCCCCCCC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O1)O[Si](C)(C)C | 4657.3 | Semi standard non polar | 33892256 | Asitribin,1TBDMS,isomer #1 | CCCCCCC(CCCC(O)C1CCC(C2CCC(C(O)CCCCCCCCCCCCC3=CC(C)OC3=O)O2)O1)O[Si](C)(C)C(C)(C)C | 4998.2 | Semi standard non polar | 33892256 | Asitribin,1TBDMS,isomer #2 | CCCCCCC(O)CCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C2CCC(C(O)CCCCCCCCCCCCC3=CC(C)OC3=O)O2)O1 | 4979.6 | Semi standard non polar | 33892256 | Asitribin,1TBDMS,isomer #3 | CCCCCCC(O)CCCC(O)C1CCC(C2CCC(C(CCCCCCCCCCCCC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O1 | 4971.5 | Semi standard non polar | 33892256 | Asitribin,2TBDMS,isomer #1 | CCCCCCC(CCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C2CCC(C(O)CCCCCCCCCCCCC3=CC(C)OC3=O)O2)O1)O[Si](C)(C)C(C)(C)C | 5141.1 | Semi standard non polar | 33892256 | Asitribin,2TBDMS,isomer #2 | CCCCCCC(CCCC(O)C1CCC(C2CCC(C(CCCCCCCCCCCCC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O1)O[Si](C)(C)C(C)(C)C | 5141.8 | Semi standard non polar | 33892256 | Asitribin,2TBDMS,isomer #3 | CCCCCCC(O)CCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C2CCC(C(CCCCCCCCCCCCC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O1 | 5157.8 | 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 - Asitribin GC-MS (Non-derivatized) - 70eV, Positive | splash10-00kr-0976653000-b9807c67331dbc00eb17 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS (1 TMS) - 70eV, Positive | splash10-07e0-2349517000-9e9872c3298358b1e3ea | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS (TMS_3_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitribin GC-MS ("Asitribin,1TMS,#1" TMS) - 70eV, Positive | Not Available | 2021-11-02 | 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 - Asitribin 10V, Positive-QTOF | splash10-0ab9-0111039000-3a14308df04ecbff3cfb | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitribin 20V, Positive-QTOF | splash10-0a4r-5970363000-d685651b22f2bc7eeb55 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitribin 40V, Positive-QTOF | splash10-00mx-9654230000-935e1cee5163252812b5 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitribin 10V, Negative-QTOF | splash10-00di-0000039000-2f0e1d4f7250c6ba81fc | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitribin 20V, Negative-QTOF | splash10-0umr-2444239000-2faa5a767143f8cbf323 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitribin 40V, Negative-QTOF | splash10-0705-2393230000-a10aa84d11015ef194cd | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitribin 10V, Positive-QTOF | splash10-052r-0000195000-4d8dd82b574e41448141 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitribin 20V, Positive-QTOF | splash10-0adr-1000196000-84eff765d3d5ebdd6566 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitribin 40V, Positive-QTOF | splash10-0007-9500000000-8de5e424dcac470db749 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitribin 10V, Negative-QTOF | splash10-00di-0000009000-d75fc29eaef399def629 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitribin 20V, Negative-QTOF | splash10-00di-2122229000-bcbb886d8626e1aa3904 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitribin 40V, Negative-QTOF | splash10-00kr-7447904000-6189de5367f81a748c9d | 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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