T2 Toxin
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Basic Info
| Common Name | T2 Toxin(F04916) |
| 2D Structure | |
| Description | T2 Toxin is isolated from Fusarium species and Trichoderma lignorum. T2 Toxin is an important mycotoxin occurring naturally in various agricultural products. |
| FRCD ID | F04916 |
| CAS Number | 21259-20-1 |
| PubChem CID | 529495 |
| Formula | C24H34O9 |
| IUPAC Name | None |
| InChI Key | BXFOFFBJRFZBQZ-UHFFFAOYSA-N |
| InChI | InChI=1S/C24H34O9/c1-12(2)7-18(27)32-16-9-23(10-29-14(4)25)17(8-13(16)3)33-21-19(28)20(31-15(5)26)22(23,6)24(21)11-30-24/h8,12,16-17,19-21,28H,7,9-11H2,1-6H3 |
| Canonical SMILES | CC1=CC2C(CC1OC(=O)CC(C)C)(C3(C(C(C(C34CO4)O2)O)OC(=O)C)C)COC(=O)C |
| Isomeric SMILES | CC1=CC2C(CC1OC(=O)CC(C)C)(C3(C(C(C(C34CO4)O2)O)OC(=O)C)C)COC(=O)C |
| Wikipedia | T2 Toxin |
| Synonyms |
MLS002703014
Epoxytrichothecene
T-2 TOXIN
SMR001566822
Insariotoxin
Fusariotoxin T2
T-2 mycotoxin
Fusariotoxin T 2
T 2 Toxin
Toxin T 2
|
| 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 - Tricarboxylic acid or derivatives - Fatty acid ester - Oxepane - Oxane - Fatty acyl - Cyclic alcohol - Secondary alcohol - Carboxylic acid ester - Oxacycle - Ether - Oxirane - Dialkyl ether - Carboxylic acid derivative - Organoheterocyclic compound - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organic oxygen compound - Alcohol - Carbonyl group - 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 | 466.527 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 9 |
| Complexity | 881 |
| Monoisotopic Mass | 466.22 |
| Exact Mass | 466.22 |
| XLogP | 0.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 33 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 8 |
| 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+ | 0.8033 |
| Human Intestinal Absorption | HIA+ | 0.8456 |
| Caco-2 Permeability | Caco2- | 0.6652 |
| P-glycoprotein Substrate | Substrate | 0.7872 |
| P-glycoprotein Inhibitor | Inhibitor | 0.8650 |
| Non-inhibitor | 0.6687 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7811 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7597 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8152 |
| CYP450 2D6 Substrate | Non-substrate | 0.8649 |
| CYP450 3A4 Substrate | Substrate | 0.7052 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8665 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8234 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9236 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8354 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9361 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8690 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9893 |
| Non-inhibitor | 0.8854 | |
| AMES Toxicity | AMES toxic | 0.5900 |
| Carcinogens | Non-carcinogens | 0.9264 |
| Fish Toxicity | High FHMT | 0.9886 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9971 |
| Honey Bee Toxicity | High HBT | 0.8670 |
| Biodegradation | Not ready biodegradable | 0.9973 |
| Acute Oral Toxicity | I | 0.8239 |
| Carcinogenicity (Three-class) | Non-required | 0.6552 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.1129 | LogS |
| Caco-2 Permeability | 0.7474 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 5.2072 | LD50, mol/kg |
| Fish Toxicity | -0.0671 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.9871 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Plasma-Based Degradation of Mycotoxins Produced by Fusarium, Aspergillus and Alternaria Species. | Toxins (Basel) | 2017 Mar 10 | 28287436 |
| Multi-mycotoxin stable isotope dilution LC-MS/MS method for Fusarium toxins in beer. | Food Chem | 2017 Mar 1 | 27719934 |
| Development of a nanoarray capable of the rapid and simultaneous detection of zearalenone, T2-toxin and fumonisin. | Talanta | 2017 Mar 1 | 28107943 |
| Multi-mycotoxin stable isotope dilution LC-MS/MS method for Fusarium toxins in cereals. | Anal Bioanal Chem | 2016 Jan | 26514672 |
| T-2 toxin regulates steroid hormone secretion of rat ovarian granulosa cells through cAMP-PKA pathway. | Toxicol Lett | 2015 Feb 3 | 25542145 |
| Real-time loop-mediated isothermal amplification (LAMP) assay for group specific detection of important trichothecene producing Fusarium species in wheat. | Int J Food Microbiol | 2014 May 2 | 24631635 |
| Nanoparticle-based pseudo hapten for target-responsive cargo release from a magnetic mesoporous silica nanocontainer. | Chem Commun (Camb) | 2014 Jun 14 | 24788827 |
| Modeling the effects of environmental conditions on HT2 and T2 toxin accumulation in field oat grains. | Phytopathology | 2014 Jan | 23883158 |
| Novel multiplex fluorescent immunoassays based on quantum dot nanolabels for mycotoxins determination. | Biosens Bioelectron | 2014 Dec 15 | 24976152 |
| 6-Plex microsphere immunoassay with imaging planar array detection for mycotoxins in barley. | Analyst | 2014 Aug 21 | 24919458 |
| Mycotoxins and mycotoxigenic fungi in poultry feed for food-producing animals. | ScientificWorldJournal | 2014 | 25126610 |
| Novel electrochemical immunoassay for quantitative monitoring of biotoxin using target-responsive cargo release from mesoporous silica nanocontainers. | Anal Chem | 2013 Oct 1 | 23998398 |
| Development and application of a method for the analysis of 9 mycotoxins in maize by HPLC-MS/MS. | J Food Sci | 2013 Nov | 24245893 |
| Development and application of salting-out assisted liquid/liquid extraction for multi-mycotoxin biomarkers analysis in pig urine with high performance liquid chromatography/tandem mass spectrometry. | J Chromatogr A | 2013 May 31 | 23177157 |
| Displacement-type quartz crystal microbalance immunosensing platform for ultrasensitive monitoring of small molecular toxins. | Anal Chem | 2013 Jul 16 | 23789727 |
| Occurrence of mycotoxins in livestock feeds and feed stuffs of Tamil Nadu. | J Environ Biol | 2013 Jul | 24640264 |
| Medical aspects of bio-terrorism. | Toxicon | 2013 Jul | 23339855 |
| Mycotoxin-degradation profile of Rhodococcus strains. | Int J Food Microbiol | 2013 Aug 16 | 23891865 |
| Determination of fusarium mycotoxins in wheat, maize and animal feed using on-line clean-up with high resolution mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2013 | 23078086 |
| Multi-mycotoxin determination in cereals and derived products marketed in Tunisia using ultra-high performance liquid chromatography coupled to triple quadrupole mass spectrometry. | Food Chem Toxicol | 2012 Jul | 22579994 |
Targets
- 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 ]
- General Function:
- Ubiquinone binding
- Specific Function:
- Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
- Gene Name:
- SDHD
- Uniprot ID:
- O14521
- Molecular Weight:
- 17042.82 Da
- Mechanism of Action:
- T-2 Toxin inhibits electron transport activity by inhibiting the succinic dehydrogenase enzyme.
References
- Rocha O, Ansari K, Doohan FM: Effects of trichothecene mycotoxins on eukaryotic cells: a review. Food Addit Contam. 2005 Apr;22(4):369-78. [16019807 ]
- General Function:
- Succinate dehydrogenase activity
- Specific Function:
- Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Can act as a tumor suppressor.
- Gene Name:
- SDHA
- Uniprot ID:
- P31040
- Molecular Weight:
- 72690.975 Da
- Mechanism of Action:
- T-2 Toxin inhibits electron transport activity by inhibiting the succinic dehydrogenase enzyme.
References
- Rocha O, Ansari K, Doohan FM: Effects of trichothecene mycotoxins on eukaryotic cells: a review. Food Addit Contam. 2005 Apr;22(4):369-78. [16019807 ]
- General Function:
- Ubiquinone binding
- Specific Function:
- Iron-sulfur protein (IP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
- Gene Name:
- SDHB
- Uniprot ID:
- P21912
- Molecular Weight:
- 31629.365 Da
- Mechanism of Action:
- T-2 Toxin inhibits electron transport activity by inhibiting the succinic dehydrogenase enzyme.
References
- Rocha O, Ansari K, Doohan FM: Effects of trichothecene mycotoxins on eukaryotic cells: a review. Food Addit Contam. 2005 Apr;22(4):369-78. [16019807 ]
- General Function:
- Succinate dehydrogenase activity
- Specific Function:
- Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
- Gene Name:
- SDHC
- Uniprot ID:
- Q99643
- Molecular Weight:
- 18610.03 Da
- Mechanism of Action:
- T-2 Toxin inhibits electron transport activity by inhibiting the succinic dehydrogenase enzyme.
References
- Rocha O, Ansari K, Doohan FM: Effects of trichothecene mycotoxins on eukaryotic cells: a review. Food Addit Contam. 2005 Apr;22(4):369-78. [16019807 ]
- 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 ]