Fusarenon-X
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Basic Info
| Common Name | Fusarenon-X(F04954) |
| 2D Structure | |
| Description | Fusarenon-X is a trichothecene. Trichothecenes are a very large family of chemically related mycotoxins produced by various species of Fusarium, Myrothecium, Trichoderma, Trichothecium, Cephalosporium, Verticimonosporium, and Stachybotrys. The most important structural features causing the biological activities of trichothecenes are: the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. They are produced on many different grains like wheat, oats or maize by various Fusarium species such as F. graminearum, F. sporotrichioides, F. poae and F. equiseti. Some molds that produce trichothecene mycotoxins, such as Stachybotrys chartarum, can grow in damp indoor environments and may contribute to health problems among building occupants. (L1948) |
| FRCD ID | F04954 |
| CAS Number | 23255-69-8 |
| PubChem CID | 304599 |
| Formula | C17H22O8 |
| IUPAC Name | None |
| InChI Key | XGCUCFKWVIWWNW-CAYGJDLQSA-N |
| InChI | InChI=1S/C17H22O8/c1-7-4-9-16(5-18,12(22)10(7)20)15(3)13(24-8(2)19)11(21)14(25-9)17(15)6-23-17/h4,9,11-14,18,21-22H,5-6H2,1-3H3/t9-,11-,12-,13-,14-,15-,16-,17+/m1/s1 |
| Canonical SMILES | CC1=CC2C(C(C1=O)O)(C3(C(C(C(C34CO4)O2)O)OC(=O)C)C)CO |
| Isomeric SMILES | CC1=C[C@@H]2[C@]([C@@H](C1=O)O)([C@]3([C@@H]([C@H]([C@H]([C@@]34CO4)O2)O)OC(=O)C)C)CO |
| Synonyms |
FUSARENON X
Fusarenone X
Fusarenon-X
UNII-0CV8D1DR96
Fusarenon
23255-69-8
0CV8D1DR96
Nivalenol monoacetate
NSC197211
Nivalenol-4-O-acetate
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Sesquiterpenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Trichothecenes |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Trichothecene skeleton - Cyclohexenone - Oxepane - Oxane - Cyclic alcohol - Carboxylic acid ester - Ketone - Cyclic ketone - Secondary alcohol - Carboxylic acid derivative - Dialkyl ether - Oxirane - Ether - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Carbonyl group - Alcohol - Hydrocarbon derivative - Organic oxygen compound - Organooxygen compound - Organic oxide - Primary alcohol - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 354.355 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 3 |
| Complexity | 688 |
| Monoisotopic Mass | 354.131 |
| Exact Mass | 354.131 |
| XLogP | -1.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 25 |
| Defined Atom Stereocenter Count | 8 |
| 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+ | 0.5271 |
| Human Intestinal Absorption | HIA+ | 0.6698 |
| Caco-2 Permeability | Caco2- | 0.8239 |
| P-glycoprotein Substrate | Substrate | 0.8060 |
| P-glycoprotein Inhibitor | Inhibitor | 0.5204 |
| Non-inhibitor | 0.6862 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7962 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6442 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8138 |
| CYP450 2D6 Substrate | Non-substrate | 0.8614 |
| CYP450 3A4 Substrate | Substrate | 0.6121 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8588 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8346 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9249 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8473 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9405 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7805 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9885 |
| Non-inhibitor | 0.7423 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.9452 |
| Fish Toxicity | High FHMT | 0.9345 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9386 |
| Honey Bee Toxicity | High HBT | 0.8622 |
| Biodegradation | Not ready biodegradable | 0.9973 |
| Acute Oral Toxicity | I | 0.8112 |
| Carcinogenicity (Three-class) | Non-required | 0.7700 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.9501 | LogS |
| Caco-2 Permeability | 0.1080 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.9155 | LD50, mol/kg |
| Fish Toxicity | 0.6304 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5421 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Determination of multiple mycotoxins in feedstuffs by combined use of UPLC-MS/MS and UPLC-QTOF-MS. | Food Chem | 2018 Nov 30 | 29934148 |
| First study on trichothecene and zearalenone exposure of the Romanian population through wheat-based products consumption. | Food Chem Toxicol | 2018 Nov | 30213551 |
| Liquid chromatography - high resolution mass spectrometry method for monitoring of 17 mycotoxins in human plasma for exposure studies. | J Chromatogr A | 2018 May 4 | 29576275 |
| UDP-Glucosyltransferases from Rice, Brachypodium, and Barley: Substrate Specificities and Synthesis of Type A and B Trichothecene-3-O-β-d-glucosides. | Toxins (Basel) | 2018 Mar 6 | 29509722 |
| Evaluation of Mycotoxin Residues on Ready-to-Eat Food by Chromatographic Methods Coupled to Mass Spectrometry in Tandem. | Toxins (Basel) | 2018 Jun 15 | 29914055 |
| Mycotoxin contamination of sorghum and its contribution to human dietary exposure in four sub-Saharan countries. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018 Jul | 29912638 |
| Short communication: Analysis of mycotoxins in Spanish milk. | J Dairy Sci | 2018 Jan | 29055539 |
| Multiple mycotoxin analysis in nut products: Occurrence and risk characterization. | Food Chem Toxicol | 2018 Apr | 29458161 |
| Determination of Fusarium toxins in functional vegetable milks applying salting-out-assisted liquid-liquid extraction combined with ultra-high-performance liquid chromatography tandem mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2017 Nov | 28820044 |
| In silico analysis sheds light on the structural basis underlying the ribotoxicity of trichothecenes-A tool for supporting the hazard identification process. | Toxicol Lett | 2017 Mar 15 | 28216416 |
| Multi-Mycotoxin Analysis in Durum Wheat Pasta by Liquid Chromatography Coupled to Quadrupole Orbitrap Mass Spectrometry. | Toxins (Basel) | 2017 Feb 9 | 28208797 |
| Intestinal toxicity of the type B trichothecene mycotoxin fusarenon-X: wholetranscriptome profiling reveals new signaling pathways. | Sci Rep | 2017 Aug 8 | 28790326 |
| Occurrence of Fusarium Mycotoxins in Cereal Crops and Processed Products (Ogi) from Nigeria. | Toxins (Basel) | 2016 Nov 18 | 27869703 |
| Fungal biotransformation of chlorogenic and caffeic acids by Fusarium graminearum: New insights in the contribution of phenolic acids to resistance to deoxynivalenol accumulation in cereals. | Int J Food Microbiol | 2016 Mar 16 | 26812586 |
| Development and Validation of an Ultra-High Performance Liquid Chromatography-Tandem Mass Spectrometry Method for Simultaneous Determination of Four Type B Trichothecenes and Masked Deoxynivalenol in Various Feed Products. | Molecules | 2016 Jun 8 | 27338321 |
| Fusarenon-X-induced apoptosis in the liver, kidney, and spleen of mice. | J Toxicol Pathol | 2016 Jul | 27559248 |
| Multi-mycotoxin stable isotope dilution LC-MS/MS method for Fusarium toxins in cereals. | Anal Bioanal Chem | 2016 Jan | 26514672 |
| Multimycotoxin analysis in water and fish plasma by liquid chromatography-tandem mass spectrometry. | Chemosphere | 2016 Feb | 26694790 |
| Modeling the emetic potencies of food-borne trichothecenes by benchmark dose methodology. | Food Chem Toxicol | 2016 Aug | 27292944 |
| Analysis of trichothecenes in laboratory rat feed by gas chromatography-tandem mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2016 | 26616914 |
Targets
- General Function:
- Structural constituent of ribosome
- Gene Name:
- MRPS5
- Uniprot ID:
- P82675
- Molecular Weight:
- 48006.135 Da
- Mechanism of Action:
- Trichothecenes move freely across the plasma membrane and bind specifically to ribosomes with high-affinity. Specifically, they interfere with the active site of peptidyl transferase at the 3'-end of large 28S ribosomal RNA and inhibit the initiation, elongation or termination step of protein synthesis, as well as cause polyribosomal disaggregation. Trichothecenes are cytotoxic because protein synthesis is an essential function in all tissues. Additionally, binding to ribosomes is thought to activate proteins in downstream signalling events related to immune response and apoptosis, such as mitogen-activated protein kinases. This is known as ribotoxic stress response.
References
- Pestka JJ: Mechanisms of deoxynivalenol-induced gene expression and apoptosis. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2008 Sep;25(9):1128-40. [19238623 ]
- General Function:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]