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 18:22:36 UTC |
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Update Date | 2022-03-07 02:53:47 UTC |
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HMDB ID | HMDB0033628 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Asitrilobin B |
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Description | Asitrilobin B, also known as annonacin, 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 Asitrilobin B. |
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Structure | CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCC(O)CCCCCC(O)CC1=CC(C)OC1=O InChI=1S/C35H64O7/c1-3-4-5-6-7-8-9-10-11-15-21-31(38)33-23-24-34(42-33)32(39)22-17-16-19-29(36)18-13-12-14-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3 |
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Synonyms | Value | Source |
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Annonacin | HMDB | Asitrilobin b | MeSH |
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Chemical Formula | C35H64O7 |
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Average Molecular Weight | 596.8785 |
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Monoisotopic Molecular Weight | 596.465204402 |
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IUPAC Name | 5-methyl-3-{2,8,13-trihydroxy-13-[5-(1-hydroxytridecyl)oxolan-2-yl]tridecyl}-2,5-dihydrofuran-2-one |
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Traditional Name | annonacin |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCC(O)CCCCCC(O)CC1=CC(C)OC1=O |
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InChI Identifier | InChI=1S/C35H64O7/c1-3-4-5-6-7-8-9-10-11-15-21-31(38)33-23-24-34(42-33)32(39)22-17-16-19-29(36)18-13-12-14-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3 |
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InChI Key | XNODZYPOIPVPRF-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
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Oxacycle
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Polyol
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Alcohol
- 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 | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 65.3 - 68.4 °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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Asitrilobin B,1TMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(O)CCCCC(O)CCCCCC(O)CC2=CC(C)OC2=O)O1 | 4654.9 | Semi standard non polar | 33892256 | Asitrilobin B,1TMS,isomer #2 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCC(O)CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4651.8 | Semi standard non polar | 33892256 | Asitrilobin B,1TMS,isomer #3 | CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4677.4 | Semi standard non polar | 33892256 | Asitrilobin B,1TMS,isomer #4 | CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4671.0 | Semi standard non polar | 33892256 | Asitrilobin B,2TMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(CCCCC(O)CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4618.0 | Semi standard non polar | 33892256 | Asitrilobin B,2TMS,isomer #2 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(O)CCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4612.2 | Semi standard non polar | 33892256 | Asitrilobin B,2TMS,isomer #3 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(O)CCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4608.9 | Semi standard non polar | 33892256 | Asitrilobin B,2TMS,isomer #4 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4609.6 | Semi standard non polar | 33892256 | Asitrilobin B,2TMS,isomer #5 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4606.0 | Semi standard non polar | 33892256 | Asitrilobin B,2TMS,isomer #6 | CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCC(CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4609.3 | Semi standard non polar | 33892256 | Asitrilobin B,3TMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(CCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4545.2 | Semi standard non polar | 33892256 | Asitrilobin B,3TMS,isomer #2 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(CCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4528.5 | Semi standard non polar | 33892256 | Asitrilobin B,3TMS,isomer #3 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(O)CCCCC(CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4516.2 | Semi standard non polar | 33892256 | Asitrilobin B,3TMS,isomer #4 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCC(CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4513.2 | Semi standard non polar | 33892256 | Asitrilobin B,4TMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(CCCCC(CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4437.3 | Semi standard non polar | 33892256 | Asitrilobin B,1TBDMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(O)CCCCC(O)CCCCCC(O)CC2=CC(C)OC2=O)O1 | 4877.9 | Semi standard non polar | 33892256 | Asitrilobin B,1TBDMS,isomer #2 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCC(O)CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 4875.9 | Semi standard non polar | 33892256 | Asitrilobin B,1TBDMS,isomer #3 | CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 4898.9 | Semi standard non polar | 33892256 | Asitrilobin B,1TBDMS,isomer #4 | CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 4898.3 | Semi standard non polar | 33892256 | Asitrilobin B,2TBDMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(CCCCC(O)CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 5060.0 | Semi standard non polar | 33892256 | Asitrilobin B,2TBDMS,isomer #2 | CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(O)CCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 5065.5 | Semi standard non polar | 33892256 | Asitrilobin B,2TBDMS,isomer #3 | CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(O)CCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 5065.6 | Semi standard non polar | 33892256 | Asitrilobin B,2TBDMS,isomer #4 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1 | 5062.6 | Semi standard non polar | 33892256 | Asitrilobin B,2TBDMS,isomer #5 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1 | 5063.4 | Semi standard non polar | 33892256 | Asitrilobin B,2TBDMS,isomer #6 | CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCC(CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1 | 5086.1 | 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 - Asitrilobin B GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ftk-3279340000-416a6f6afa628e4830f6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (1 TMS) - 70eV, Positive | splash10-0zmm-3029214000-cf325db24233c55a1956 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_2_6) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_3_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_3_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_3_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_3_4) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TMS_4_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TBDMS_1_4) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TBDMS_2_4) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Asitrilobin B GC-MS (TBDMS_2_5) - 70eV, Positive | Not Available | 2021-10-16 | 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 - Asitrilobin B 10V, Positive-QTOF | splash10-01t9-0000090000-3acdde40f72cf72f2086 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 20V, Positive-QTOF | splash10-040r-3951560000-269cdc8d34f72edde3fe | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 40V, Positive-QTOF | splash10-02t9-6942140000-1c8d9333362adf5aac4f | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 10V, Positive-QTOF | splash10-01t9-0000090000-3acdde40f72cf72f2086 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 20V, Positive-QTOF | splash10-040r-3951560000-269cdc8d34f72edde3fe | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 40V, Positive-QTOF | splash10-02t9-6942140000-1c8d9333362adf5aac4f | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 10V, Positive-QTOF | splash10-01t9-0000090000-3acdde40f72cf72f2086 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 20V, Positive-QTOF | splash10-040r-3951560000-269cdc8d34f72edde3fe | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 40V, Positive-QTOF | splash10-02t9-6942140000-1c8d9333362adf5aac4f | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 10V, Negative-QTOF | splash10-0002-0000090000-21572a657e5fbb661d22 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 20V, Negative-QTOF | splash10-0002-9321250000-84bb563b738e56501d19 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 40V, Negative-QTOF | splash10-002g-5395320000-91b1426da0a339a6db09 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 10V, Negative-QTOF | splash10-0002-0000090000-21572a657e5fbb661d22 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 20V, Negative-QTOF | splash10-0002-9321250000-84bb563b738e56501d19 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 40V, Negative-QTOF | splash10-002g-5395320000-91b1426da0a339a6db09 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 10V, Negative-QTOF | splash10-0002-0000090000-21572a657e5fbb661d22 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 20V, Negative-QTOF | splash10-0002-9321250000-84bb563b738e56501d19 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 40V, Negative-QTOF | splash10-002g-5395320000-91b1426da0a339a6db09 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 10V, Positive-QTOF | splash10-03di-1012290000-1db640798e3561a4e675 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 20V, Positive-QTOF | splash10-03dr-3102390000-fb99925543431a1244f0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 40V, Positive-QTOF | splash10-0536-9101100000-b2d6b89332d0a7422825 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 10V, Negative-QTOF | splash10-0002-2000190000-e1c5072df45d46a9ab09 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 20V, Negative-QTOF | splash10-002b-2527690000-0b895604e4309d2f50eb | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Asitrilobin B 40V, Negative-QTOF | splash10-00n0-9377420000-6aa863e1e47c9bfa6142 | 2021-09-23 | Wishart Lab | View Spectrum |
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