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 | HMDB0029959 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Asiminenin A |
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Description | Asiminenin A 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 Asiminenin A. |
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Structure | CCCCCCCCCC\C=C/CCC(O)C1CCC(O1)C(O)CCCCCCCCCCC(O)CC1=CC(C)OC1=O InChI=1S/C37H66O6/c1-3-4-5-6-7-8-9-10-11-15-18-21-24-33(39)35-26-27-36(43-35)34(40)25-22-19-16-13-12-14-17-20-23-32(38)29-31-28-30(2)42-37(31)41/h15,18,28,30,32-36,38-40H,3-14,16-17,19-27,29H2,1-2H3/b18-15- |
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Synonyms | Not Available |
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Chemical Formula | C37H66O6 |
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Average Molecular Weight | 606.9163 |
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Monoisotopic Molecular Weight | 606.485939844 |
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IUPAC Name | 3-(2,13-dihydroxy-13-{5-[(4Z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}tridecyl)-5-methyl-2,5-dihydrofuran-2-one |
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Traditional Name | 3-(2,13-dihydroxy-13-{5-[(4Z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}tridecyl)-5-methyl-5H-furan-2-one |
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CAS Registry Number | 168075-11-4 |
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SMILES | CCCCCCCCCC\C=C/CCC(O)C1CCC(O1)C(O)CCCCCCCCCCC(O)CC1=CC(C)OC1=O |
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InChI Identifier | InChI=1S/C37H66O6/c1-3-4-5-6-7-8-9-10-11-15-18-21-24-33(39)35-26-27-36(43-35)34(40)25-22-19-16-13-12-14-17-20-23-32(38)29-31-28-30(2)42-37(31)41/h15,18,28,30,32-36,38-40H,3-14,16-17,19-27,29H2,1-2H3/b18-15- |
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InChI Key | OZWNHDYKRQUFSF-SDXDJHTJSA-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 | 58 - 59 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 7.1e-07 mg/L @ 25 °C (est) | The Good Scents Company Information System | 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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Asiminenin A,1TMS,isomer #1 | CCCCCCCCCC/C=C\CCC(O[Si](C)(C)C)C1CCC(C(O)CCCCCCCCCCC(O)CC2=CC(C)OC2=O)O1 | 4664.9 | Semi standard non polar | 33892256 | Asiminenin A,1TMS,isomer #2 | CCCCCCCCCC/C=C\CCC(O)C1CCC(C(CCCCCCCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4661.6 | Semi standard non polar | 33892256 | Asiminenin A,1TMS,isomer #3 | CCCCCCCCCC/C=C\CCC(O)C1CCC(C(O)CCCCCCCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4687.0 | Semi standard non polar | 33892256 | Asiminenin A,2TMS,isomer #1 | CCCCCCCCCC/C=C\CCC(O[Si](C)(C)C)C1CCC(C(CCCCCCCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4589.7 | Semi standard non polar | 33892256 | Asiminenin A,2TMS,isomer #2 | CCCCCCCCCC/C=C\CCC(O[Si](C)(C)C)C1CCC(C(O)CCCCCCCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4587.8 | Semi standard non polar | 33892256 | Asiminenin A,2TMS,isomer #3 | CCCCCCCCCC/C=C\CCC(O)C1CCC(C(CCCCCCCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4584.4 | Semi standard non polar | 33892256 | Asiminenin A,3TMS,isomer #1 | CCCCCCCCCC/C=C\CCC(O[Si](C)(C)C)C1CCC(C(CCCCCCCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4518.3 | Semi standard non polar | 33892256 | Asiminenin A,1TBDMS,isomer #1 | CCCCCCCCCC/C=C\CCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(O)CCCCCCCCCCC(O)CC2=CC(C)OC2=O)O1 | 4881.3 | Semi standard non polar | 33892256 | Asiminenin A,1TBDMS,isomer #2 | CCCCCCCCCC/C=C\CCC(O)C1CCC(C(CCCCCCCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 4881.1 | Semi standard non polar | 33892256 | Asiminenin A,1TBDMS,isomer #3 | CCCCCCCCCC/C=C\CCC(O)C1CCC(C(O)CCCCCCCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 4912.0 | Semi standard non polar | 33892256 | Asiminenin A,2TBDMS,isomer #1 | CCCCCCCCCC/C=C\CCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(CCCCCCCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 5034.4 | Semi standard non polar | 33892256 | Asiminenin A,2TBDMS,isomer #2 | CCCCCCCCCC/C=C\CCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(O)CCCCCCCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 5045.5 | Semi standard non polar | 33892256 | Asiminenin A,2TBDMS,isomer #3 | CCCCCCCCCC/C=C\CCC(O)C1CCC(C(CCCCCCCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1 | 5048.4 | 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 - Asiminenin A GC-MS (Non-derivatized) - 70eV, Positive | splash10-000t-1597330000-6ca41454084244107540 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS (1 TMS) - 70eV, Positive | splash10-0g02-2492433000-2f08aa896dec6d41ab0b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS (TMS_3_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asiminenin A GC-MS ("Asiminenin A,1TMS,#1" TMS) - 70eV, Positive | Not Available | 2021-10-20 | 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 - Asiminenin A 10V, Positive-QTOF | splash10-052r-0111093000-6a05d4aa9e4e28f8a0e4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asiminenin A 20V, Positive-QTOF | splash10-01ow-1941340000-1f4884ab5d777c001aea | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asiminenin A 40V, Positive-QTOF | splash10-01ow-4942030000-798933ff35d7a79086b4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asiminenin A 10V, Negative-QTOF | splash10-0a4i-1110069000-55477bbf8ba778f3dc8b | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asiminenin A 20V, Negative-QTOF | splash10-0002-9232131000-8e132fcdcbc584d66eec | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asiminenin A 40V, Negative-QTOF | splash10-01b9-5198130000-3250751e892f10c44668 | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asiminenin A 10V, Negative-QTOF | splash10-0a4i-2100009000-c627267bd6065d41b4eb | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asiminenin A 20V, Negative-QTOF | splash10-0bt9-5677559000-c39bab3e51d8397ba4c2 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asiminenin A 40V, Negative-QTOF | splash10-02t9-9233020000-36d202d0c5873ac7629a | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asiminenin A 10V, Positive-QTOF | splash10-00dr-1121491000-72047383c900d9b4135e | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asiminenin A 20V, Positive-QTOF | splash10-00y0-6101291000-52eb110ff22b52cc3c35 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asiminenin A 40V, Positive-QTOF | splash10-0006-9101000000-6f4a3e00e67c86517ef8 | 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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