Showing metabocard for Alternariol-9-methyl ether (MMDBc0001158)
Microbial
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| Version | 1.0 | |||||||||||||||
| Status | Detected and Quantified | |||||||||||||||
| Creation Date | 2021-05-14 18:45:08 UTC | |||||||||||||||
| Update Date | 2022-08-12 19:56:25 UTC | |||||||||||||||
| Metabolite ID | MMDBc0001158 | |||||||||||||||
| Metabolite Identification | ||||||||||||||||
| Common Name | Alternariol-9-methyl ether | |||||||||||||||
| Description | Alternariol methyl ether, also known as AME, belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Alternariol methyl ether is metabolized by microsomes in the liver, preferentially at aromatic positions. It is also demethylated to alternariol. Alternariol methyl ether is an altertoxin, which is a mycotoxin of Alternaria fungi. It has demonstrated DNA-damaging activities such as single-strand and double-strand DNA breaks, DNA-intercalating, and DNA cross-linking, as well as induction of DNA repair synthesis and inhibition of DNA replication. Alternariol methyl ether has been shown to have genotoxic and mutagenic properties. Alternariol methyl ether is an extremely weak basic (essentially neutral) compound (based on its pKa). Alternariol methyl ether is a potentially toxic compound. Studies have shown altertoxins to be toxic, genotoxic, mutagenic, and carcinogenic. These effects are thought to be at least partially due to its ability to bind to the DNA minor groove with high affinity, which inhibits the activity of DNA-acting enzymes such as topoisomerase. The products of aromatic hydroxylation are either catechols or hydroquinones, which may form reactive semiquinones and quinones or undergo redox cycling. | |||||||||||||||
| Structure |  | |||||||||||||||
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| Molecular Formula | C15H12O5 | |||||||||||||||
| Average Mass | 272.2528 | |||||||||||||||
| Monoisotopic Mass | 272.068473494 | |||||||||||||||
| IUPAC Name | Not Available | |||||||||||||||
| Traditional Name | Not Available | |||||||||||||||
| CAS Registry Number | Not Available | |||||||||||||||
| SMILES | Not Available | |||||||||||||||
| InChI Identifier | InChI=1S/C15H12O5/c1-7-3-8(16)4-12-13(7)10-5-9(19-2)6-11(17)14(10)15(18)20-12/h3-6,16-17H,1-2H3 | |||||||||||||||
| InChI Key | LCSDQFNUYFTXMT-UHFFFAOYSA-N | |||||||||||||||
| Chemical Taxonomy | ||||||||||||||||
| Description | Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). | |||||||||||||||
| Kingdom | Organic compounds | |||||||||||||||
| Super Class | Phenylpropanoids and polyketides | |||||||||||||||
| Class | Coumarins and derivatives | |||||||||||||||
| Sub Class | Not Available | |||||||||||||||
| Direct Parent | Coumarins and derivatives | |||||||||||||||
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| Substituents |
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| Molecular Framework | Aromatic heteropolycyclic compounds | |||||||||||||||
| External Descriptors | Not Available | |||||||||||||||
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| Physical Properties | ||||||||||||||||
| State | Expected Solid | |||||||||||||||
| Predicted Properties | Not Available | |||||||||||||||
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| Cellular Locations | Not Available | |||||||||||||||
| Biospecimen Locations | Not Available | |||||||||||||||
| Tissue Locations | Not Available | |||||||||||||||
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| Pathways | This table shows at most 5 pathways. For the full list of associated pathways: See All Associated Bacterial Pathways
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Reactions This table shows at most 20 reactions. For the full list of associated reactions: See All Associated Reactions
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| HMDB ID | Not Available | |||||||||||||||
| DrugBank ID | Not Available | |||||||||||||||
| Phenol Explorer Compound ID | Not Available | |||||||||||||||
| FooDB ID | Not Available | |||||||||||||||
| KNApSAcK ID | Not Available | |||||||||||||||
| Chemspider ID | Not Available | |||||||||||||||
| KEGG Compound ID | Not Available | |||||||||||||||
| BioCyc ID | Not Available | |||||||||||||||
| BiGG ID | Not Available | |||||||||||||||
| Wikipedia Link | Not Available | |||||||||||||||
| METLIN ID | Not Available | |||||||||||||||
| PubChem Compound | 5360741 | |||||||||||||||
| PDB ID | Not Available | |||||||||||||||
| ChEBI ID | 141315 | |||||||||||||||
| Food Biomarker Ontology | Not Available | |||||||||||||||
| CMMC Knowledgebase | Not Available | |||||||||||||||
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| Synthesis Reference | Not Available | |||||||||||||||
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