Monoacetoxyscirpenol
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Basic Info
| Common Name | Monoacetoxyscirpenol(F04946) |
| 2D Structure | |
| Description | Monoacetoxyscirpenol is a mycotoxin from Fusarium roseum and Fusarium sulphureum Monoacetoxyscirpenol 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 | F04946 |
| CAS Number | 2623-22-5 |
| PubChem CID | 429922 |
| Formula | C17H24O6 |
| IUPAC Name | None |
| InChI Key | IRXDUBNENLKYTC-UHFFFAOYSA-N |
| InChI | InChI=1S/C17H24O6/c1-9-4-5-16(7-21-10(2)18)11(6-9)23-14-12(19)13(20)15(16,3)17(14)8-22-17/h6,11-14,19-20H,4-5,7-8H2,1-3H3 |
| Canonical SMILES | CC1=CC2C(CC1)(C3(C(C(C(C34CO4)O2)O)O)C)COC(=O)C |
| Isomeric SMILES | CC1=CC2C(CC1)(C3(C(C(C(C34CO4)O2)O)O)C)COC(=O)C |
| Synonyms |
Desacetylanguidine
Deacetylanguidin
Monoacetoxyscirpenol
15-Acetoxyscirpenol
4-Deacetylanguidin
15-Acetylscirpenetriol
15-O-Acetylscirpenetriol
15-Mono-O-acetylscirpenol
15-Acetoxyscirpen-3,4-diol
NSC 267030
|
| 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 - Oxane - Cyclic alcohol - 1,2-diol - Carboxylic acid ester - Secondary alcohol - Monocarboxylic acid or derivatives - Ether - Oxirane - Dialkyl ether - Carboxylic acid derivative - Oxacycle - 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 | 324.373 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 3 |
| Complexity | 588 |
| Monoisotopic Mass | 324.157 |
| Exact Mass | 324.157 |
| XLogP | -0.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 23 |
| 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+ | 0.7045 |
| Human Intestinal Absorption | HIA+ | 0.5330 |
| Caco-2 Permeability | Caco2- | 0.7600 |
| P-glycoprotein Substrate | Substrate | 0.8803 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.5053 |
| Non-inhibitor | 0.5761 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7545 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7414 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8342 |
| CYP450 2D6 Substrate | Non-substrate | 0.8513 |
| CYP450 3A4 Substrate | Substrate | 0.7286 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7064 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7981 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9137 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7934 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9587 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8799 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9733 |
| Inhibitor | 0.5700 | |
| AMES Toxicity | Non AMES toxic | 0.8995 |
| Carcinogens | Non-carcinogens | 0.9533 |
| Fish Toxicity | High FHMT | 0.9893 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9972 |
| Honey Bee Toxicity | High HBT | 0.8389 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | I | 0.7590 |
| Carcinogenicity (Three-class) | Non-required | 0.6356 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.3361 | LogS |
| Caco-2 Permeability | 0.2158 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.9952 | LD50, mol/kg |
| Fish Toxicity | 0.5782 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.0137 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Development of a liquid chromatography-tandem mass spectrometry with ultrasound-assisted extraction and auto solid-phase clean-up method for the determination of Fusarium toxins in animal derived foods. | J Chromatogr A | 2013 Oct 11 | 24011505 |
| Detection of type A trichothecene di-glucosides produced in corn by high-resolution liquid chromatography-Orbitrap mass spectrometry. | Toxins (Basel) | 2013 Mar 22 | 23524332 |
| Occurrence and distribution of 13 trichothecene toxins in naturally contaminated maize plants in Germany. | Toxins (Basel) | 2012 Oct | 23162697 |
| Pathogenicity, symptom development, and mycotoxin formation in wheat by Fusarium species frequently isolated from sugar beet. | Phytopathology | 2011 Nov | 21635142 |
| Metabolic pathways of trichothecenes. | Drug Metab Rev | 2010 May | 19678805 |
| Determination of trichothecenes in wheat grain without sample cleanup using comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry. | J Chromatogr A | 2008 Dec 26 | 19036380 |
| Fusarium toxins of the scirpentriol subgroup: a review. | Mycopathologia | 2007 Sep | 17610049 |
| Occurrence of Fusarium species and trichothecenes in Nigerian maize. | Int J Food Microbiol | 2007 May 30 | 17412440 |
| Natural occurrence of Fusarium toxins in soy food marketed in Germany. | Int J Food Microbiol | 2007 Jan 25 | 16854487 |
| Degradation of trichothecene mycotoxins by chicken intestinal microbes. | Food Chem Toxicol | 2007 Jan | 17011105 |
| Occurrence of type A trichothecenes in conventionally and organically produced oats and oat products. | Mol Nutr Food Res | 2007 Dec | 18030660 |
| Synthesis of four carbon-13-labeled type a trichothecene mycotoxins and their application as internal standards in stable isotope dilution assays. | J Agric Food Chem | 2006 Sep 6 | 16939307 |
| Natural occurrence of 16 fusarium toxins in grains and feedstuffs of plant origin from Germany. | Mycopathologia | 2006 Jan | 16389484 |
| Determination of 12 type A and B trichothecenes in cereals by liquid chromatography-electrospray ionization tandem mass spectrometry. | J Agric Food Chem | 2005 Nov 16 | 16277381 |
| Fusarium toxin contents of maize and maize products purchased in the years 2000 and 2001 in Germany. | Mycotoxin Res | 2005 Mar | 23605202 |
| Determination of mycotoxins in bovine milk by liquid chromatography tandem mass spectrometry. | J Chromatogr B Analyt Technol Biomed Life Sci | 2005 Jun 25 | 15899372 |
| Survey of Fusarium toxins in foodstuffs of plant origin marketed in Germany. | Int J Food Microbiol | 2005 Jan 1 | 15582742 |
| Report from SCOOP task 3.2.10 "collection of occurrence data of Fusarium toxins in food and assessment of dietary intake by the population of EU member states". Subtask: trichothecenes. | Toxicol Lett | 2004 Oct 10 | 15342090 |
| Simultaneous quantification of A-trichothecene mycotoxins in grains using liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. | J Chromatogr A | 2002 Aug 30 | 12236496 |
| [The metabolism of trichothecenes in swine]. | Dtsch Tierarztl Wochenschr | 1995 Jan | 7781540 |
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:
- 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 ]