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 17:45:11 UTC |
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Update Date | 2022-03-07 02:53:06 UTC |
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HMDB ID | HMDB0031749 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Annomutacin |
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Description | Annomutacin 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 Annomutacin. |
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Structure | CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCCC(O)CCCCCC(O)CC1=CC(C)OC1=O InChI=1S/C37H68O7/c1-3-4-5-6-7-8-9-10-11-18-23-33(40)35-25-26-36(44-35)34(41)24-19-13-12-15-20-31(38)21-16-14-17-22-32(39)28-30-27-29(2)43-37(30)42/h27,29,31-36,38-41H,3-26,28H2,1-2H3 |
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Synonyms | Value | Source |
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cis-Annomontacin | MeSH, HMDB | Annomutacin | MeSH | Annomontacin | MeSH |
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Chemical Formula | C37H68O7 |
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Average Molecular Weight | 624.9316 |
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Monoisotopic Molecular Weight | 624.49650453 |
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IUPAC Name | 5-methyl-3-{2,8,15-trihydroxy-15-[5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-2,5-dihydrofuran-2-one |
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Traditional Name | 5-methyl-3-{2,8,15-trihydroxy-15-[5-(1-hydroxytridecyl)oxolan-2-yl]pentadecyl}-5H-furan-2-one |
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CAS Registry Number | 170900-29-5 |
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SMILES | CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCCC(O)CCCCCC(O)CC1=CC(C)OC1=O |
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InChI Identifier | InChI=1S/C37H68O7/c1-3-4-5-6-7-8-9-10-11-18-23-33(40)35-25-26-36(44-35)34(41)24-19-13-12-15-20-31(38)21-16-14-17-22-32(39)28-30-27-29(2)43-37(30)42/h27,29,31-36,38-41H,3-26,28H2,1-2H3 |
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InChI Key | ALYPJDVVTYTPDW-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 | 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 | 7.3e-06 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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Annomutacin,1TMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(O)CCCCCCC(O)CCCCCC(O)CC2=CC(C)OC2=O)O1 | 4850.2 | Semi standard non polar | 33892256 | Annomutacin,1TMS,isomer #2 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCCCC(O)CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4850.7 | Semi standard non polar | 33892256 | Annomutacin,1TMS,isomer #3 | CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4879.4 | Semi standard non polar | 33892256 | Annomutacin,1TMS,isomer #4 | CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4865.8 | Semi standard non polar | 33892256 | Annomutacin,2TMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(CCCCCCC(O)CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4808.5 | Semi standard non polar | 33892256 | Annomutacin,2TMS,isomer #2 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(O)CCCCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4812.1 | Semi standard non polar | 33892256 | Annomutacin,2TMS,isomer #3 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(O)CCCCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O1 | 4796.2 | Semi standard non polar | 33892256 | Annomutacin,2TMS,isomer #4 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4812.8 | Semi standard non polar | 33892256 | Annomutacin,2TMS,isomer #5 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4797.0 | Semi standard non polar | 33892256 | Annomutacin,2TMS,isomer #6 | CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCCCC(CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4811.1 | Semi standard non polar | 33892256 | Annomutacin,3TMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(CCCCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4748.4 | Semi standard non polar | 33892256 | Annomutacin,3TMS,isomer #2 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(CCCCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4719.9 | Semi standard non polar | 33892256 | Annomutacin,3TMS,isomer #3 | CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(O)CCCCCCC(CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4712.0 | Semi standard non polar | 33892256 | Annomutacin,3TMS,isomer #4 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCCCC(CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O1 | 4712.7 | Semi standard non polar | 33892256 | Annomutacin,1TBDMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(O)CCCCCCC(O)CCCCCC(O)CC2=CC(C)OC2=O)O1 | 5071.5 | Semi standard non polar | 33892256 | Annomutacin,1TBDMS,isomer #2 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCCCC(O)CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 5071.5 | Semi standard non polar | 33892256 | Annomutacin,1TBDMS,isomer #3 | CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 5096.1 | Semi standard non polar | 33892256 | Annomutacin,1TBDMS,isomer #4 | CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 5091.7 | Semi standard non polar | 33892256 | Annomutacin,2TBDMS,isomer #1 | CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(CCCCCCC(O)CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 5254.2 | Semi standard non polar | 33892256 | Annomutacin,2TBDMS,isomer #2 | CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(O)CCCCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 5259.6 | Semi standard non polar | 33892256 | Annomutacin,2TBDMS,isomer #3 | CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(O)CCCCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1 | 5253.7 | Semi standard non polar | 33892256 | Annomutacin,2TBDMS,isomer #4 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCCCC(CCCCCC(O)CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1 | 5259.4 | Semi standard non polar | 33892256 | Annomutacin,2TBDMS,isomer #5 | CCCCCCCCCCCCC(O)C1CCC(C(CCCCCCC(O)CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1 | 5253.5 | Semi standard non polar | 33892256 | Annomutacin,2TBDMS,isomer #6 | CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCCCC(CCCCCC(CC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1 | 5282.1 | 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 - Annomutacin GC-MS (Non-derivatized) - 70eV, Positive | splash10-07dk-3385914000-a0952058915a5e081fdd | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (1 TMS) - 70eV, Positive | splash10-00bl-4029325000-fa0e1729e28e84fd8106 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TMS_2_6) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TMS_3_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TMS_3_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TMS_3_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TMS_3_4) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TBDMS_1_4) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TBDMS_2_4) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TBDMS_2_5) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Annomutacin GC-MS (TBDMS_2_6) - 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 - Annomutacin 10V, Positive-QTOF | splash10-0a4r-0001069000-3c5ec96918a2d0286354 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annomutacin 20V, Positive-QTOF | splash10-0a4i-3824192000-3bc6e93bd7706f37050a | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annomutacin 40V, Positive-QTOF | splash10-05n0-4933150000-4628cdccd487c6867481 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annomutacin 10V, Negative-QTOF | splash10-00di-1100039000-5119cd42f16afc07bdbe | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annomutacin 20V, Negative-QTOF | splash10-0002-9321134000-8bb0d1131613f3042351 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annomutacin 40V, Negative-QTOF | splash10-052g-5395160000-4124033bf64bd708b61c | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annomutacin 10V, Positive-QTOF | splash10-000i-1011393000-d1ae008aa199a9d65153 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annomutacin 20V, Positive-QTOF | splash10-000i-2001592000-7ab9e79d0a95fcc7fa92 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annomutacin 40V, Positive-QTOF | splash10-052f-9001400000-f2b04162125f572b80b3 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annomutacin 10V, Negative-QTOF | splash10-00di-2000119000-9a27d6b793774e4c7e21 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annomutacin 20V, Negative-QTOF | splash10-074j-2734739000-0582a650436e4efccb4b | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Annomutacin 40V, Negative-QTOF | splash10-0900-7416920000-99ec6a914f6d4aeb0c6d | 2021-09-23 | Wishart Lab | View Spectrum |
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