Acetyldeoxynivalenol
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Basic Info
| Common Name | Acetyldeoxynivalenol(F04947) |
| 2D Structure | |
| Description | Acetyldeoxynivalenol is found in cereals and cereal products. Toxin from infected barley Acetyldeoxynivalenol belongs to the family of Trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzoyran derivative with a variant number of hydroxyl, acetly, or other substituents [1]. (Reference: [1] http://www.inchem.org/documents/ehc/ehc/ehc105.htm). |
| FRCD ID | F04947 |
| CAS Number | 50722-38-8 |
| PubChem CID | 104759 |
| Formula | C17H22O7 |
| IUPAC Name | None |
| InChI Key | ADFIQZBYNGPCGY-UHFFFAOYSA-N |
| InChI | InChI=1S/C17H22O7/c1-8-4-11-16(6-18,13(21)12(8)20)15(3)5-10(23-9(2)19)14(24-11)17(15)7-22-17/h4,10-11,13-14,18,21H,5-7H2,1-3H3 |
| Canonical SMILES | CC1=CC2C(C(C1=O)O)(C3(CC(C(C34CO4)O2)OC(=O)C)C)CO |
| Isomeric SMILES | CC1=CC2C(C(C1=O)O)(C3(CC(C(C34CO4)O2)OC(=O)C)C)CO |
| Synonyms |
3-Acetyldeoxynivalenol
3-Acetyl don
Deoxynivalenol monoacetate
Dehydronivalenol monoacetate
Acetyldeoxynivalenol
NSC267036
NSC 267036
AC1Q6OAD
AC1L2XG2
ADFIQZBYNGPCGY-UHFFFAOYSA-N
|
| 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 - Oxepane - Cyclohexenone - Oxane - Carboxylic acid ester - Ketone - Secondary alcohol - Cyclic ketone - Monocarboxylic acid or derivatives - Ether - Oxirane - Dialkyl ether - Carboxylic acid derivative - Organoheterocyclic compound - Oxacycle - Carbonyl group - Primary alcohol - Organic oxide - Organic oxygen compound - Organooxygen compound - Alcohol - Hydrocarbon derivative - 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 | 338.356 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 3 |
| Complexity | 657 |
| Monoisotopic Mass | 338.137 |
| Exact Mass | 338.137 |
| XLogP | -0.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 24 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 7 |
| 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+ | 0.6662 |
| Human Intestinal Absorption | HIA+ | 0.6799 |
| Caco-2 Permeability | Caco2- | 0.8922 |
| P-glycoprotein Substrate | Substrate | 0.8518 |
| P-glycoprotein Inhibitor | Inhibitor | 0.6664 |
| Non-inhibitor | 0.7010 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8114 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6986 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8370 |
| CYP450 2D6 Substrate | Non-substrate | 0.8706 |
| CYP450 3A4 Substrate | Substrate | 0.6865 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8867 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8414 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9460 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8894 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8704 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8857 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9844 |
| Non-inhibitor | 0.5787 | |
| AMES Toxicity | Non AMES toxic | 0.9163 |
| Carcinogens | Non-carcinogens | 0.9467 |
| Fish Toxicity | High FHMT | 0.9531 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9899 |
| Honey Bee Toxicity | High HBT | 0.8395 |
| Biodegradation | Not ready biodegradable | 0.9973 |
| Acute Oral Toxicity | I | 0.7797 |
| Carcinogenicity (Three-class) | Non-required | 0.6975 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.8318 | LogS |
| Caco-2 Permeability | -0.0625 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.5674 | LD50, mol/kg |
| Fish Toxicity | 0.8383 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.8179 | 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 |
| Regional differences in the composition of Fusarium Head Blight pathogens and mycotoxins associated with wheat in Mexico. | Int J Food Microbiol | 2018 May 20 | 29554557 |
| Deoxynivalenol and its acetyl derivatives in bread and biscuits in Shandong province of China. | Food Addit Contam Part B Surveill | 2018 Mar | 29125057 |
| Clinical impact of deoxynivalenol, 3-acetyl-deoxynivalenol and 15-acetyl-deoxynivalenol on the severity of an experimental Mycoplasma hyopneumoniae infection in pigs. | BMC Vet Res | 2018 Jun 18 | 29914486 |
| The prevalence of deoxynivalenol and its derivatives in the spring wheat grain from different agricultural production systems in Lithuania. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018 Jun | 29337657 |
| Short communication: Analysis of mycotoxins in Spanish milk. | J Dairy Sci | 2018 Jan | 29055539 |
| Species composition, toxigenic potential and aggressiveness of Fusarium isolates causing Head Blight of barley in Uruguay. | Food Microbiol | 2018 Dec | 30166170 |
| Mycobiota and co-occurrence of mycotoxins in South African maize-based opaque beer. | Int J Food Microbiol | 2018 Apr 2 | 29453120 |
| 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 |
| Multiple metabolic pathways for metabolism of l-tryptophan in Fusarium graminearum. | Can J Microbiol | 2017 Nov | 28926717 |
| Multi-mycotoxin stable isotope dilution LC-MS/MS method for Fusarium toxins in beer. | Food Chem | 2017 Mar 1 | 27719934 |
| Fate of Fusarium Toxins during Brewing. | J Agric Food Chem | 2017 Jan 11 | 27931101 |
| Comparative in vitro cytotoxicity of modified deoxynivalenol on porcine intestinal epithelial cells. | Food Chem Toxicol | 2016 Sep | 27338712 |
| Indole-3-acetic acid in Fusarium graminearum: Identification of biosynthetic pathways and characterization of physiological effects. | Fungal Biol | 2016 Sep | 27567719 |
| Endocrine activity of mycotoxins and mycotoxin mixtures. | Food Chem Toxicol | 2016 Oct | 27481073 |
| Effect of preceding crop on Fusarium species and mycotoxin contamination of wheat grains. | J Sci Food Agric | 2016 Oct | 26867679 |
| Temporal dynamics, population characterization and mycotoxins accumulation of Fusarium graminearum in Eastern China. | Sci Rep | 2016 Nov 17 | 27853184 |
| Occurrence of 26 Mycotoxins in the Grain of Cereals Cultivated in Poland. | Toxins (Basel) | 2016 May 25 | 27231939 |
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 ]