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 22:21:37 UTC |
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Update Date | 2022-03-07 02:55:11 UTC |
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HMDB ID | HMDB0037117 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Neoannonin B |
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Description | Neoannonin B 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 Neoannonin B. |
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Structure | CCCCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCC1=CC(C)OC1=O InChI=1S/C37H66O6/c1-3-4-5-6-7-8-9-13-16-19-22-31(38)33-24-26-35(42-33)36-27-25-34(43-36)32(39)23-20-17-14-11-10-12-15-18-21-30-28-29(2)41-37(30)40/h28-29,31-36,38-39H,3-27H2,1-2H3 |
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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-(11-hydroxy-11-{5-[5-(1-hydroxytridecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-5-methyl-2,5-dihydrofuran-2-one |
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Traditional Name | 3-(11-hydroxy-11-{5-[5-(1-hydroxytridecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-5-methyl-5H-furan-2-one |
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CAS Registry Number | 170312-94-4 |
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SMILES | CCCCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCC1=CC(C)OC1=O |
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InChI Identifier | InChI=1S/C37H66O6/c1-3-4-5-6-7-8-9-13-16-19-22-31(38)33-24-26-35(42-33)36-27-25-34(43-36)32(39)23-20-17-14-11-10-12-15-18-21-30-28-29(2)41-37(30)40/h28-29,31-36,38-39H,3-27H2,1-2H3 |
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InChI Key | SOAPDULPHQDKCM-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 | |
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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 | 4.5e-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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Neoannonin B,1TMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(O)CCCCCCCCCCC3=CC(C)OC3=O)O2)O1 | 4580.5 | Semi standard non polar | 33892256 | Neoannonin B,1TMS,isomer #2 | CCCCCCCCCCCCC(O)C1CCC(C2CCC(C(CCCCCCCCCCC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O1 | 4580.5 | Semi standard non polar | 33892256 | Neoannonin B,2TMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(CCCCCCCCCCC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O1 | 4525.0 | Semi standard non polar | 33892256 | Neoannonin B,1TBDMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C2CCC(C(O)CCCCCCCCCCC3=CC(C)OC3=O)O2)O1 | 4799.6 | Semi standard non polar | 33892256 | Neoannonin B,1TBDMS,isomer #2 | CCCCCCCCCCCCC(O)C1CCC(C2CCC(C(CCCCCCCCCCC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O1 | 4799.6 | Semi standard non polar | 33892256 | Neoannonin B,2TBDMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C2CCC(C(CCCCCCCCCCC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O1 | 4969.9 | 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 - Neoannonin B GC-MS (Non-derivatized) - 70eV, Positive | splash10-03y0-0649320000-8644119696b489143c5e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neoannonin B GC-MS (1 TMS) - 70eV, Positive | splash10-03dr-4038923000-2f97c3ac6231fddab5fd | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neoannonin B GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neoannonin B GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neoannonin B GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neoannonin B GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neoannonin B GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Neoannonin B GC-MS ("Neoannonin B,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 - Neoannonin B 10V, Positive-QTOF | splash10-0a4r-0133098000-9f7de3b5f9ab685881d7 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neoannonin B 20V, Positive-QTOF | splash10-00kr-1931140000-a6ee684cedfa8920dc53 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neoannonin B 40V, Positive-QTOF | splash10-014i-4932010000-57830c75af441fad8793 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neoannonin B 10V, Negative-QTOF | splash10-0a4i-1000049000-99dea8b81b848f7a392f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neoannonin B 20V, Negative-QTOF | splash10-052r-1555293000-24570c04bef3f84bdad0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neoannonin B 40V, Negative-QTOF | splash10-07vu-2249030000-3015b9005c2f76548289 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neoannonin B 10V, Positive-QTOF | splash10-059i-1001193000-2b5d422f71e3240d0dc5 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neoannonin B 20V, Positive-QTOF | splash10-052r-3000091000-1560d8dc70ab7b57dd1f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neoannonin B 40V, Positive-QTOF | splash10-0006-9000100000-c148762775975148561a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neoannonin B 10V, Negative-QTOF | splash10-0a4i-0000109000-849a958c634ee7f4923e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neoannonin B 20V, Negative-QTOF | splash10-0a4i-4132349000-f46fac416a2db57bbce3 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Neoannonin B 40V, Negative-QTOF | splash10-0ap0-9337631000-c522b57aeee9beea1bca | 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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