15-acetyldeoxynivalenol : A trichothecene mycotoxin that is deoxynivalenol acetylated on the oxygen at C-15. A skin and eye irritant, along with its 3-acetyl regioisomer and its parent deoxynivalenol it is considered among the most commonly and widely distributed cereal contaminants. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 10382483 |
| CHEMBL ID | 468823 |
| CHEBI ID | 146194 |
| MeSH ID | M0135344 |
| Synonym |
|---|
| 15-o-acetyl-4-deoxynivalenol from fusarium graminearum |
| trichothec-9-en-8-one, 15-(acetyloxy)-12,13-epoxy-3,7-dihydroxy-, (3-alpha,7-alpha)- |
| 15-acetyldeoxynivalenol |
| 15-acetylvomitoxin |
| 15-acetyl deoxynivalenol |
| 15-monoacetyldeoxynivalenol |
| CHEMBL468823 |
| 3alpha,7alpha-dihydroxy-8-oxo-12,13-epoxytrichothec-9-en-15-yl acetate |
| 15-acetyl-deoxynivalenol |
| 15-(acetyloxy)-12,13-epoxy-3alpha,7alpha-dihydroxytrichothec-9-en-8-one |
| 88337-96-6 |
| 15-acdon |
| 15-acetyl-don |
| (3alpha,7alpha)-15-(acetyloxy)-12,13-epoxy-3,7-dihydroxytrichothec-9-en-8-one |
| CHEBI:146194 |
| 0430x4r3z1 , |
| unii-0430x4r3z1 |
| 15-o-acetyl-4-deoxynivalenol |
| deoxynivalenol 15-acetate |
| AKOS015913371 |
| vomitoxin 15-acetate |
| 3.alpha.,7.alpha.)-15-(acetyloxy)-12,13-epoxy-3,7-dihydroxytrichothec-9-en-8-one |
| 15-acetyldeoxynivalenol, reference material |
| DTXSID20891851 |
| 15-acetyl-deoxynivalenol 99% |
| Q26840875 |
| 15-acetoxy-3alpha,7alpha-dihydroxy-12,13-epoxytrichothec-9-en-8-one |
| HY-N6683 |
| CS-0099690 |
| [(1r,2r,3s,7r,9r,10r,12s)-3,10-dihydroxy-1,5-dimethyl-4-oxospiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-2-yl]methyl acetate |
| 15-acetyl-deoxynivalenol 100 microg/ml in acetonitrile |
| 15-acetyl deoxynivalenol (~90%) |
| acetyldeoxynivalenol, 15- |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Trichothecene mycotoxins, toxic natural products of fungi from the family Hypocreaceae, are potent inhibitors of protein synthesis." | ( 3D QSAR study of the toxicity of trichothecene mycotoxins. Lin, A; Rodarte, CB; Steinmetz, WE, 2009) | 0.35 |
| " On proliferating cells, 3-ADON was less toxic than DON, which was less toxic than 15-ADON." | ( Toxicity of deoxynivalenol and its acetylated derivatives on the intestine: differential effects on morphology, barrier function, tight junction proteins, and mitogen-activated protein kinases. Bracarense, AP; Callu, P; Grosjean, F; Kolf-Clauw, M; Laffitte, J; Lucioli, J; Lyazhri, F; Oswald, IP; Pinton, P; Tsybulskyy, D, 2012) | 0.38 |
| " These results indicate that the simultaneous presence of low doses of mycotoxins in food commodities and diet may be more toxic than predicted from the mycotoxins alone." | ( New insights into mycotoxin mixtures: the toxicity of low doses of Type B trichothecenes on intestinal epithelial cells is synergistic. Abiola, FA; Abrami, R; Alassane-Kpembi, I; Gauthier, T; Kolf-Clauw, M; Oswald, IP; Puel, O, 2013) | 0.39 |
| " Among all three mycotoxins assayed, deoxynivalenol (DON) derivated presented the highest toxic potential." | ( Cytotoxic effects and degradation products of three mycotoxins: alternariol, 3-acetyl-deoxynivalenol and 15-acetyl-deoxynivalenol in liver hepatocellular carcinoma cells. Juan, C; Juan-García, A; König, S; Ruiz, MJ, 2015) | 0.42 |
| " In the present work it is determined and evaluated the toxic effects of binary and tertiary combination treatment of HepG2 cells with AOH, 3-ADON and 15-ADON, by using the MTT assay (3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide), to subsequently apply the isobologram method and elucidate if the mixtures of these mycotoxins produced synergism, antagonism or additive effect; and lastly, to analyze mycotoxins conversion into metabolites produced and released by HepG2 cells after applying the treatment conditions by liquid chromatography tandem mass spectrometry (LC-MS/MS) equipment and extracted from culture media." | ( Binary and tertiary combination of alternariol, 3-acetyl-deoxynivalenol and 15-acetyl-deoxynivalenol on HepG2 cells: Toxic effects and evaluation of degradation products. Juan, C; Juan-García, A; Manyes, L; Ruiz, MJ, 2016) | 0.43 |
| " The data reported here support the hypothesis that QUE rescues the toxic effects of DON or 15ADON due to the similar mechanisms of DON and 15ADON toxicity." | ( Metabolomic profiling reveals similar cytotoxic effects and protective functions of quercetin during deoxynivalenol- and 15-acetyl deoxynivalenol-induced cell apoptosis. Jia, BX; Liu, N; Wu, A; Yang, YX; Yu, S, 2020) | 0.56 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " For pigs receiving 15-ADON and DON ip, increased dosage was associated with decreased average time to vomition, increased duration of emesis and increased average number of vomitions." | ( Emetic activity of the trichothecene 15-acetyldeoxynivalenol in swine. Lin, WS; Miller, ER; Pestka, JJ, 1987) | 0.55 |
| " While emesis induced by intraperitoneally dosed to DON in the mink has been related to plasma up-grading of 5-hydroxytryptamine (5-HT) and neurotransmitters peptide YY (PYY), the impact of oral dosing with DON or its four congeners on secretion of these chemical substances have not been established." | ( Emesis to trichothecene deoxynivalenol and its congeners correspond to secretion of peptide YY and 5-HT. Guo, X; Kuca, K; Qin, Z; Wei, B; Wu, Q; Wu, W; Xiao, H; Xu, B, 2023) | 0.91 |
| Role | Description |
|---|---|
| epitope | The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds. |
| mycotoxin | Poisonous substance produced by fungi. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| trichothecene | Any one of a large family of chemically related mycotoxins with a structure based on a sesquiterpene skeleton. The most important structural features causing the biological activities of trichothecenes are a 12,13-epoxy ring, the presence of hydroxy or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID467615 | Cytotoxicity against yeast cells relative to Tetraol | 2009 | European journal of medicinal chemistry, Nov, Volume: 44, Issue:11 | 3D QSAR study of the toxicity of trichothecene mycotoxins. |
| AID382888 | Toxicity in mouse CD4+ T cells assessed as induction of IL5 at 500 ng/ml | 2008 | Journal of natural products, Apr, Volume: 71, Issue:4 | Structure and conformational dynamics of trichothecene mycotoxins. |
| AID1090742 | Phytotoxicity against Arabidopsis thaliana Col-4 leaves assessed as induction of chlorosis, shriveling or death of leaves after 7 weeks post compound application by detached leaf assay | 2007 | Journal of agricultural and food chemistry, Aug-08, Volume: 55, Issue:16 | Structure-activity relationships of trichothecene toxins in an Arabidopsis thaliana leaf assay. |
| AID467617 | Cytotoxicity against yeast cells assessed as logarithm of ratio of toxicity of test compound to Tetraol | 2009 | European journal of medicinal chemistry, Nov, Volume: 44, Issue:11 | 3D QSAR study of the toxicity of trichothecene mycotoxins. |
| AID1090743 | Phytotoxicity against Arabidopsis thaliana Col-4 leaves assessed as induction of leaf death after 7 weeks post compound application by detached leaf assay | 2007 | Journal of agricultural and food chemistry, Aug-08, Volume: 55, Issue:16 | Structure-activity relationships of trichothecene toxins in an Arabidopsis thaliana leaf assay. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 5 (4.95) | 18.7374 |
| 1990's | 2 (1.98) | 18.2507 |
| 2000's | 13 (12.87) | 29.6817 |
| 2010's | 62 (61.39) | 24.3611 |
| 2020's | 19 (18.81) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (21.35) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 4 (3.85%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 100 (96.15%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||