Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-11 01:12:56 UTC |
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Update Date | 2021-09-26 22:58:06 UTC |
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HMDB ID | HMDB0248043 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one |
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Description | Aflatoxicol belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Antioxidants such as ellagic acid and inducers of some cytochromes P450, such as indole-3-carbinol, may give a protective effect. Aflatoxicol is an extremely weak basic (essentially neutral) compound (based on its pKa). Aflatoxicol is a potentially toxic compound. Aflatoxicol is a metabolite of aflatoxin B1, one of the mycotoxins from Aspergillus flavus and A. parasiticus. Aflatoxins are metabolized in the liver by the cytochrome P-450-dependent polysubstrate mono-oxygenase system to less toxic metabolites. Singlet oxygen in turn activates them to mutagens and DNA binding species. Protracted exposure to aflatoxins may cause liver damage and necrosis, cholestasis, and hepatomas. Aflatoxins modify the immune system by affecting antibody formation, complement, cell-mediated immunity, and phagocytosis. This compound has been identified in human blood as reported by (PMID: 31557052 ). (3s,7r)-16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | COC1=C2C3=C(C(O)CC3)C(=O)OC2=C2C3C=COC3OC2=C1 InChI=1S/C17H14O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8-9,17-18H,2-3H2,1H3 |
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Synonyms | Value | Source |
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Aflatoxicol, (1R-(1alpha,6aalpha,9aalpha))-isomer | MeSH | Aflatoxin R | MeSH |
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Chemical Formula | C17H14O6 |
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Average Molecular Weight | 314.2895 |
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Monoisotopic Molecular Weight | 314.07903818 |
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IUPAC Name | 16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1,4,9,11,13(17)-pentaen-18-one |
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Traditional Name | 16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1,4,9,11,13(17)-pentaen-18-one |
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CAS Registry Number | Not Available |
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SMILES | COC1=C2C3=C(C(O)CC3)C(=O)OC2=C2C3C=COC3OC2=C1 |
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InChI Identifier | InChI=1S/C17H14O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8-9,17-18H,2-3H2,1H3 |
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InChI Key | WYIWLDSPNDMZIT-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Coumarins and derivatives |
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Sub Class | Furanocoumarins |
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Direct Parent | Angular furanocoumarins |
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Alternative Parents | |
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Substituents | - Angular furanocoumarin
- Benzopyran
- 1-benzopyran
- Coumaran
- Anisole
- Alkyl aryl ether
- Pyranone
- Benzenoid
- Pyran
- Heteroaromatic compound
- Dihydrofuran
- Secondary alcohol
- Lactone
- Acetal
- Oxacycle
- Organoheterocyclic compound
- Ether
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | 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 | 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 IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TMS,isomer #1 | COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C)CC1)C1C=COC1O2 | 2945.1 | Semi standard non polar | 33892256 | (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TMS,isomer #1 | COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C)CC1)C1C=COC1O2 | 2811.1 | Standard non polar | 33892256 | (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TMS,isomer #1 | COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C)CC1)C1C=COC1O2 | 4009.7 | Standard polar | 33892256 | (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TBDMS,isomer #1 | COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C(C)(C)C)CC1)C1C=COC1O2 | 3170.7 | Semi standard non polar | 33892256 | (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TBDMS,isomer #1 | COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C(C)(C)C)CC1)C1C=COC1O2 | 3050.6 | Standard non polar | 33892256 | (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TBDMS,isomer #1 | COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C(C)(C)C)CC1)C1C=COC1O2 | 4064.5 | Standard 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 - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one GC-MS (Non-derivatized) - 70eV, Positive | splash10-00ds-0090000000-3383a3871ef632b3b597 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | 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 - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 10V, Positive-QTOF | splash10-00kb-0095000000-71c58c811fa86c4f350f | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 20V, Positive-QTOF | splash10-00kb-0092000000-25d664ddf6f71729d9c9 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 40V, Positive-QTOF | splash10-07xs-2390000000-d8e7c756bedcdafe8d00 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 10V, Negative-QTOF | splash10-03di-0059000000-7536a2ca78d64e601ad7 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 20V, Negative-QTOF | splash10-03dj-0094000000-bdac8584ca3c38da05b2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 40V, Negative-QTOF | splash10-0gb9-3190000000-f6139c8985207a374eaa | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 10V, Negative-QTOF | splash10-03di-0009000000-7c7169b7540bc9455826 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 20V, Negative-QTOF | splash10-03di-0039000000-cf442be2c6395255469f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 40V, Negative-QTOF | splash10-03xs-0292000000-729af1d7e1ce8cc5d258 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 10V, Positive-QTOF | splash10-014i-0029000000-c8d393f9a78874956ee0 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 20V, Positive-QTOF | splash10-014i-0029000000-c8d393f9a78874956ee0 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 40V, Positive-QTOF | splash10-0a4i-0090000000-6efb3590dae7ff13062b | 2021-10-12 | Wishart Lab | View Spectrum |
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