Moniliformin
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Basic Info
| Common Name | Moniliformin(F05013) |
| 2D Structure | |
| Description | Moniliformin is a mycotoxin produced by a number of fungi of the Fusarium species. It can by found in contaminated cereal crops and is known to be a lethal food contaminant to fowl as well as a cause of Kashin-Beck disease in humans. (L1969, A3075) |
| FRCD ID | F05013 |
| CAS Number | 71376-34-6 |
| PubChem CID | 40452 |
| Formula | C4H2O3 |
| IUPAC Name | 3-hydroxycyclobut-3-ene-1,2-dione |
| InChI Key | KGPQKNJSZNXOPV-UHFFFAOYSA-N |
| InChI | InChI=1S/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H |
| Canonical SMILES | C1=C(C(=O)C1=O)O |
| Isomeric SMILES | C1=C(C(=O)C1=O)O |
| Wikipedia | Moniliformin |
| Synonyms |
Moniliformin
Semisquaric acid
31876-38-7
Hydroxycyclobutenedione
3-Cyclobutene-1,2-dione, 3-hydroxy-
Cyclobutenedione, hydroxy-
3-Hydroxy-3-cyclobutenedione
CCRIS 4943
1-Hydroxycyclobut-1-ene-3,4-dione
3-Hydroxy-3-cyclobutene-1,2-dione
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Vinylogous acids |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Vinylogous acids |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Vinylogous acid - Cyclic ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 98.057 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Complexity | 166 |
| Monoisotopic Mass | 98 |
| Exact Mass | 98 |
| XLogP | -0.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 7 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8272 |
| Human Intestinal Absorption | HIA+ | 0.9943 |
| Caco-2 Permeability | Caco2+ | 0.5740 |
| P-glycoprotein Substrate | Non-substrate | 0.7643 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7400 |
| Non-inhibitor | 0.9629 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9072 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8100 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8670 |
| CYP450 2D6 Substrate | Non-substrate | 0.9145 |
| CYP450 3A4 Substrate | Non-substrate | 0.7187 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8722 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9394 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9232 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9201 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9454 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9557 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9655 |
| Non-inhibitor | 0.9838 | |
| AMES Toxicity | Non AMES toxic | 0.8635 |
| Carcinogens | Non-carcinogens | 0.7551 |
| Fish Toxicity | High FHMT | 0.5245 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9091 |
| Honey Bee Toxicity | High HBT | 0.8106 |
| Biodegradation | Ready biodegradable | 0.9039 |
| Acute Oral Toxicity | I | 0.7783 |
| Carcinogenicity (Three-class) | Non-required | 0.5231 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.8281 | LogS |
| Caco-2 Permeability | 1.0198 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.3152 | LD50, mol/kg |
| Fish Toxicity | 1.0601 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2499 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Fusarium species and moniliformin occurrence in sorghum grains used as ingredient for animal feed in Argentina. | J Sci Food Agric | 2018 May 23 | 29797405 |
| Effect of Prothioconazole Application Timing on Fusarium Mycotoxin Content in Maize Grain. | J Agric Food Chem | 2018 May 16 | 29681149 |
| A rapid LC-MS/MS method for the determination of moniliformin and occurrence of this mycotoxin in maize products from the Bavarian market. | Mycotoxin Res | 2018 Mar | 28844121 |
| Effects of fusariotoxin co-exposure on THP-1 human immune cells. | Cell Biol Toxicol | 2018 Jun | 28822000 |
| Causal agents of Fusarium head blight of durum wheat (Triticum durum Desf.) in central Italy and their in vitro biosynthesis of secondary metabolites. | Food Microbiol | 2018 Apr | 29173624 |
| Fusarium proliferatum - Causal agent of garlic bulb rot in Spain: Genetic variability and mycotoxin production. | Food Microbiol | 2017 Oct | 28648292 |
| Hepatotoxicity of fusariotoxins, alone and in combination, towards the HepaRG human hepatocyte cell line. | Food Chem Toxicol | 2017 Nov | 28935499 |
| Survey of moniliformin in wheat- and corn-based products using a straightforward analytical method. | Mycotoxin Res | 2017 Nov | 28791630 |
| The effect of fertiliser treatments on the severity of Fusarium head blight and mycotoxin biosynthesis in winter rye. | Arh Hig Rada Toksikol | 2017 Mar 1 | 28365678 |
| Mycotoxin risk assessment for consumers of groundnut in domestic markets in Nigeria. | Int J Food Microbiol | 2017 Jun 19 | 28380344 |
| Emerging Fusarium and Alternaria Mycotoxins: Occurrence, Toxicity and Toxicokinetics. | Toxins (Basel) | 2017 Jul 18 | 28718805 |
| Emerging Mycotoxins: Beyond Traditionally Determined Food Contaminants. | J Agric Food Chem | 2017 Aug 23 | 27599910 |
| Dual effectiveness of Alternaria but not Fusarium mycotoxins against human topoisomerase II and bacterial gyrase. | Arch Toxicol | 2017 Apr | 27682608 |
| Mould and mycotoxin exposure assessment of melon and bush mango seeds, two common soup thickeners consumed in Nigeria. | Int J Food Microbiol | 2016 Nov 21 | 27543818 |
| Effect of Fusarium-Derived Metabolites on the Barrier Integrity of Differentiated Intestinal Porcine Epithelial Cells (IPEC-J2). | Toxins (Basel) | 2016 Nov 19 | 27869761 |
| Four-locus phylogeny of Fusarium avenaceum and related species and theirspecies-specific identification based on partial phosphate permease genesequences. | Int J Food Microbiol | 2016 May 16 | 26974249 |
| Wildly Growing Asparagus (Asparagus officinalis L.) Hosts Pathogenic Fusarium Species and Accumulates Their Mycotoxins. | Microb Ecol | 2016 May | 26687343 |
| Updated survey of Fusarium species and toxins in Finnish cereal grains. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2016 May | 27002810 |
| Production of the Fusarium Mycotoxin Moniliformin by Penicillium melanoconidium. | J Agric Food Chem | 2016 Jun 8 | 27195914 |
| Relationship between Fusarium spp. diversity and mycotoxin contents of mature grains in southern Belgium. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2016 Jul | 27181458 |
Targets
- General Function:
- Glyceraldehyde oxidoreductase activity
- Specific Function:
- Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
- Gene Name:
- AKR1B1
- Uniprot ID:
- P15121
- Molecular Weight:
- 35853.125 Da
- Mechanism of Action:
- Moniliformin has been shown to interfere with carbohydrate metabolism by inhibiting transketolase and aldose reductase.
References
- Jestoi M: Emerging fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin: a review. Crit Rev Food Sci Nutr. 2008 Jan;48(1):21-49. doi: 10.1080/10408390601062021. [18274964 ]
- General Function:
- Thiamine pyrophosphate binding
- Specific Function:
- The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
- Gene Name:
- OGDH
- Uniprot ID:
- Q02218
- Molecular Weight:
- 115934.37 Da
- Mechanism of Action:
- Moniliformin reversibly inhibits the enzymes pyruvate dehydrogenase and alpha-ketoglutarate dehydrogenase by competing for the binding site of pyruvate. This interferes with the tricarboxylic acid cycle by preventing the necessary incorporation of pyruvate and oxidation of the alpha-ketoglutarate intermediate.
References
- Jestoi M: Emerging fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin: a review. Crit Rev Food Sci Nutr. 2008 Jan;48(1):21-49. doi: 10.1080/10408390601062021. [18274964 ]
- General Function:
- Pyruvate dehydrogenase activity
- Specific Function:
- The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
- Gene Name:
- PDHA1
- Uniprot ID:
- P08559
- Molecular Weight:
- 43295.255 Da
- Mechanism of Action:
- Moniliformin reversibly inhibits the enzymes pyruvate dehydrogenase and alpha-ketoglutarate dehydrogenase by competing for the binding site of pyruvate. This interferes with the tricarboxylic acid cycle by preventing the necessary incorporation of pyruvate and oxidation of the alpha-ketoglutarate intermediate.
References
- Jestoi M: Emerging fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin: a review. Crit Rev Food Sci Nutr. 2008 Jan;48(1):21-49. doi: 10.1080/10408390601062021. [18274964 ]
- General Function:
- Pyruvate dehydrogenase (acetyl-transferring) activity
- Specific Function:
- The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
- Gene Name:
- PDHA2
- Uniprot ID:
- P29803
- Molecular Weight:
- 42932.855 Da
- Mechanism of Action:
- Moniliformin reversibly inhibits the enzymes pyruvate dehydrogenase and alpha-ketoglutarate dehydrogenase by competing for the binding site of pyruvate. This interferes with the tricarboxylic acid cycle by preventing the necessary incorporation of pyruvate and oxidation of the alpha-ketoglutarate intermediate.
References
- Jestoi M: Emerging fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin: a review. Crit Rev Food Sci Nutr. 2008 Jan;48(1):21-49. doi: 10.1080/10408390601062021. [18274964 ]
- General Function:
- Pyruvate dehydrogenase activity
- Specific Function:
- The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
- Gene Name:
- PDHB
- Uniprot ID:
- P11177
- Molecular Weight:
- 39233.1 Da
- Mechanism of Action:
- Moniliformin reversibly inhibits the enzymes pyruvate dehydrogenase and alpha-ketoglutarate dehydrogenase by competing for the binding site of pyruvate. This interferes with the tricarboxylic acid cycle by preventing the necessary incorporation of pyruvate and oxidation of the alpha-ketoglutarate intermediate.
References
- Jestoi M: Emerging fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin: a review. Crit Rev Food Sci Nutr. 2008 Jan;48(1):21-49. doi: 10.1080/10408390601062021. [18274964 ]
- General Function:
- Transketolase activity
- Specific Function:
- Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
- Gene Name:
- TKT
- Uniprot ID:
- P29401
- Molecular Weight:
- 67876.95 Da
- Mechanism of Action:
- Moniliformin has been shown to interfere with carbohydrate metabolism by inhibiting transketolase and aldose reductase.
References
- Jestoi M: Emerging fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin: a review. Crit Rev Food Sci Nutr. 2008 Jan;48(1):21-49. doi: 10.1080/10408390601062021. [18274964 ]