CHEBI:10022 - deoxynivalenol

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ChEBI Name deoxynivalenol ChEBI ID CHEBI:10022 Definition A trichothecene mycotoxin produced by Fusarium to which wheat, barley, maize (corn) and their products are susceptible to contamination. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information ChemicalBook:CB0391546, eMolecules:26757232, eMolecules:474372, ZINC000005457778 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License Vomitoxin, also known as deoxynivalenol (DON), is a type B trichothecene, an epoxy-sesquiterpenoid. This mycotoxin occurs predominantly in grains such as wheat, barley, oats, rye, and corn, and less often in rice, sorghum, and triticale. The occurrence of deoxynivalenol is associated primarily with Fusarium graminearum (Gibberella zeae) and F. culmorum, both of which are important plant pathogens which cause fusarium head blight in wheat and gibberella or fusarium ear blight in corn. The incidence of fusarium head blight is strongly associated with moisture at the time of flowering (anthesis), and the timing of rainfall, rather than the amount, is the most critical factor. However, increased amount of moisture towards harvest time has been associated with lower amount of vomitoxin in wheat grain due to leaching of toxins. Furthermore, deoxynivalenol contents are significantly affected by the susceptibility of cultivars towards Fusarium species, previous crop, tillage practices, and fungicide use. It occurs abundantly in grains in Norway due to heavy rainfall. F. graminearum grows optimally at a temperature of 25 °C and at a water activity above 0.88. F. culmorum grows optimally at 21 °C and at a water activity above 0.87. The geographical distribution of the two species appears to be related to temperature, F. graminearum being the more common species occurring in warmer climates. Deoxynivalenol has been implicated in incidents of mycotoxicoses in both humans and farm animals. Read full article at Wikipedia Formula C15H20O6 Net Charge 0 Average Mass 296.319 Monoisotopic Mass 296.12599 InChI InChI=1S/C15H20O6/c1-7-3-9-14(5-16,11(19)10(7)18)13(2)4-8(17)12(21-9)15(13)6-20-15/h3,8-9,11-12,16-17,19H,4-6H2,1-2H3/t8-,9-,11-,12-,13-,14-,15+/m1/s1 InChIKey LINOMUASTDIRTM-QGRHZQQGSA-N SMILES [H][C@@]12O[C@]3([H])C=C(C)C(=O)[C@@H](O)[C@]3(CO)[C@@](C)(C[C@H]1O)[C@]21CO1 Metabolite of Species Details Fusarium (NCBI:txid5506) See: PubMed Roles Classification Biological Role(s): mycotoxin Poisonous substance produced by fungi. (via trichothecene ) View more via ChEBI Ontology ChEBI Ontology Outgoing deoxynivalenol (CHEBI:10022) has role mycotoxin (CHEBI:25442) deoxynivalenol (CHEBI:10022) is a cyclic ketone (CHEBI:3992) deoxynivalenol (CHEBI:10022) is a enone (CHEBI:51689) deoxynivalenol (CHEBI:10022) is a primary alcohol (CHEBI:15734) deoxynivalenol (CHEBI:10022) is a secondary α-hydroxy ketone (CHEBI:2468) deoxynivalenol (CHEBI:10022) is a trichothecene (CHEBI:55517) deoxynivalenol (CHEBI:10022) is a triol (CHEBI:27136) Incoming 15-acetyldeoxynivalenol (CHEBI:146194) has functional parent deoxynivalenol (CHEBI:10022) 3-acetyldeoxynivalenol (CHEBI:146195) has functional parent deoxynivalenol (CHEBI:10022) DON-10-gamma-glutamylcysteine (CHEBI:149450) has functional parent deoxynivalenol (CHEBI:10022) DON-10-glutathione (CHEBI:149452) has functional parent deoxynivalenol (CHEBI:10022) DON-10-isoleucine (CHEBI:149454) has functional parent deoxynivalenol (CHEBI:10022) DON-10-leucine (CHEBI:149456) has functional parent deoxynivalenol (CHEBI:10022) DON-10-phenylalanine (CHEBI:149457) has functional parent deoxynivalenol (CHEBI:10022) DON-10-S-cysteine (CHEBI:149447) has functional parent deoxynivalenol (CHEBI:10022) DON-10-tyrosine (CHEBI:149459) has functional parent deoxynivalenol (CHEBI:10022) DON-13-S-cysteine (CHEBI:149448) has functional parent deoxynivalenol (CHEBI:10022) DON-15-penicillin G (CHEBI:149460) has functional parent deoxynivalenol (CHEBI:10022) DON-15-sulfate (CHEBI:149455) has functional parent deoxynivalenol (CHEBI:10022) DON-3-sulfate (CHEBI:149449) has functional parent deoxynivalenol (CHEBI:10022) DON-sulfonate 1 (CHEBI:149440) has functional parent deoxynivalenol (CHEBI:10022) DON-sulfonate 2 (CHEBI:149442) has functional parent deoxynivalenol (CHEBI:10022) DON-sulfonate 3 (CHEBI:149446) has functional parent deoxynivalenol (CHEBI:10022) IUPAC Name 3α,7α,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one Synonyms Sources 3α,7α,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one ChemIDplus 4-Deoxynivalenol ChemIDplus 4-Desoxynivalenol ChemIDplus Dehydronivalenol ChemIDplus Desoxynivalenol ChemIDplus DON KEGG COMPOUND Vomitoxin KEGG COMPOUND Manual Xrefs Databases 36584 ChemSpider C00003201 KNApSAcK C09747 KEGG COMPOUND LMPR0103180002 LIPID MAPS Vomitoxin Wikipedia View more database links Registry Number Type Source 51481-10-8 CAS Registry Number ChemIDplus Citations Last Modified 23 November 2020