Compound: DEOXYNIVALENOL
SMILES: O=C1C(=C[C@H]2O[C@H]3[C@@]4([C@@]([C@]2([C@@H]1O)CO)(C[C@H]3O)C)OC4)C
InChIKey: LINOMUASTDIRTM-QGRHZQQGSA-N
Synonyms: DEOXYNIVALENOL, 51481-10-8, 4-Deoxynivalenol, Dehydronivalenol, 4-Desoxynivalenol, Desoxynivalenol, CCRIS 7801, Rd toxin, NSC 269144, JT37HYP23V, 3alpha,7alpha,15-Trihydroxy-12,13-epoxytrichothec-9-en-8-one, CHEBI:10022, 12,13-Epoxy-3-alpha,7-alpha,15-trihydroxy-9-trichothecen-8-one, NSC-269144, Trichothec-9-en-8-one, 12,13-epoxy-3,7,15-trihydroxy-, (3-alpha,7-alpha)-, (1R,2R,3S,7R,9R,10R,12S)-3,10-dihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one, (1R,2R,3S,7R,9R,10R,12S)-3,10-dihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro(8-oxatricyclo(7.2.1.02,7)dodec-5-ene-12,2'-oxirane)-4-one, 3-epi-DON, RefChem:131974, 3 alpha,7 alpha,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one, 3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro(oxirane-2,12'-tricyclo(7.2.1.02,7)dodecan)-5'-en-4'-one, 610-668-0, MFCD09039270, Trichothec-9-en-8-one, 12,13-epoxy-3,7,15-trihydroxy-, (3a,7a)-, (3beta,7alpha)-3,7,15-Trihydroxy-12,13-Epoxytrichothec-9-En-8-One, (3alpha,7alpha)-3,7,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one, Deoxynivalenol 100 microg/mL in Acetonitrile, HSDB 7245, UNII-JT37HYP23V, DEOXYNIVALENOL?, VOMITOXIN [MI], Epitope ID:910166, DEOXYNIVALENOL [HSDB], CHEMBL513300, orb1707387, SCHEMBL2694361, MSK7213, Deoxynivalenol, reference material, EX-A5479, HY-N6684, MSK7213-100A, Maize flour - Deoxynivalenol (blank), AKOS024457908, 20 - Fusarium mycotoxins in maize oil, CS-W012154, FD63586, AC-35348, AS-75858, DA-62777, Wheat flour - Deoxynivalenol (DON) blank, NS00000120, Deoxynivalenol Quality Control Sample,From wheat, Deoxynivalenol Quality Control Sample ,From wheat, Q420518, Deoxynivalenol(DON) Solution in Acetonitrile, 100ug/mL, 4-Deoxynivalenol Calibration Solution Certified Reference Material, 3.ALPHA.,7.ALPHA.,15-TRIHYDROXY-12,13-EPOXYTRICHOTHEC-9-EN-8-ONE, 4-Deoxynivalenol in acetonitrile, IRMM(R) certified Reference Material, 12,13-EPOXY-3-.ALPHA.,7-.ALPHA.,15-TRIHYDROXY-9-TRICHOTHECEN-8- ONE, Trichothec-9-en-8-one, 12,13-epoxy-3,7,15-trihydroxy-, (2?,3?,6?,7?,11?,12?)-, (1'R,2S,2'R,3'S,7'R,9'R,10'R)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0?,?]dodecan]-5'-en-4'-one, (1R,2R,3S,7R,9R,10R,12S)-3,10-dihydroxy-2-(hydroxymethyl)-1,5-dimethyl-spiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one, (2R,2'S,3R,5R,5aR,6S,9aR)-3,6-dihydroxy-5a-(hydroxymethyl)-5,8-dimethyl-2,3,4,5,5a,6-hexahydrospiro[2,5-methanobenzo[b]oxepine-10,2'-oxiran]-7(9aH)-one, (2S,2'R,3'R,5'R,5a'R,6'S,9a'R)-3',6'-dihydroxy-5a'-(hydroxymethyl)-5',8'-dimethyl-2',3',4',5',5a',9a'-hexahydrospiro[oxirane-2,10'-[2,5]methanobenzo[b]oxepin]-7'(6'H)-one, 3J6, TRICHOTHEC-9-EN-8-ONE, 12,13-EPOXY-3,7,15-TRIHYDROXY-, (3- .ALPHA.,7-.ALPHA.)-
Theoretical properties:
molecular_formula: C15H20O6
molecular_weight: 296.31 g/mol
exact_mass: 296.12598835 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 1
heavy_atom_count: 21
topological_polar_surface_area: 99.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Fine needles from ethyl acetate + petroleum ether
color: Fine needles from ethyl acetate + petroleum ether
melting_point: 151-153 °C
solubility: Soluble to 30 nM in ethanol
Descriptions:
{"pubchem": "Deoxynivalenol is a trichothecene mycotoxin produced by Fusarium to which wheat, barley, maize (corn) and their products are susceptible to contamination. It has a role as a mycotoxin. It is a primary alcohol, a secondary alpha-hydroxy ketone, a triol, a cyclic ketone, an enone and a trichothecene.", "chebi": "A trichothecene mycotoxin produced by <em>Fusarium</em> to which wheat, barley, maize (corn) and their products are susceptible to contamination.", "chembl": "DEOXYNIVALENOL is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "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.\nF. graminearum grows optimally at a temperature of 25 \u00b0C and at a water activity above 0.88. F. culmorum grows optimally at 21 \u00b0C 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."}