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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term:alternariol
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Accession:CHEBI:64983 term browser browse the term
Definition:A benzochromenone that is 6H-benzo[c]chromen-6-one which is substituted by a methyl group at position 1 and by hydroxy groups at positions 3, 7, and 9. It is the most important mycotoxin produced by the black mould Alternaria species, which are the most common mycoflora infecting small grain cereals worldwide.
Synonyms:exact_synonym: 3,7,9-trihydroxy-1-methyl-6H-benzo[c]chromen-6-one
 related_synonym: 3,4',5-trihydroxy-6'-methyldibenzo-alpha-pyrone;   3,4,4'-trihydroxy-6'-methyl-2-biphenylcarboxylic acid gamma-lactone;   3,7,9-trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one;   AOH;   Formula=C14H10O5;   InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3;   InChIKey=CEBXXEKPIIDJHL-UHFFFAOYSA-N;   SMILES=Cc1cc(O)cc2oc(=O)c3c(O)cc(O)cc3c12
 xref: CAS:641-38-3;   KEGG:C16838;   KNApSAcK:C00023663;   KNApSAcK:C00023664
 xref_mesh: MESH:C005197
 xref: PMID:15822993;   PMID:16464542;   PMID:18727009;   PMID:19530709;   PMID:20687560;   PMID:21351248;   PMID:21534631;   PMID:21579450;   PMID:22120949;   PMID:22289771;   PMID:22406678;   PMID:22510154;   PMID:22542754;   PMID:22613072;   PMID:34941720;   PMID:3899714;   PMID:4406099;   PMID:7986060;   Reaxys:244839;   Wikipedia:Alternariol


show annotations for term's descendants           Sort by:
alternariol term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G AHR aryl hydrocarbon receptor affects response to substance
multiple interactions		 ISO
EXP		 AHR protein affects the susceptibility to alternariol
[alternariol co-treated with altertoxin II co-treated with 2-methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazophenyl)amide] affects the localization of AHR protein; [alternariol co-treated with altertoxin II] promotes the reaction [IL1B protein affects the localization of AHR protein]; alternariol inhibits the reaction [altertoxin II affects the localization of AHR protein]; alternariol promotes the reaction [IL1B protein affects the localization of AHR protein]
AHR protein affects the reaction [alternariol results in increased expression of CYP1A1 protein]		 CTD PMID:22120949 PMID:35405071 NCBI chr 7:17,298,652...17,346,147
Ensembl chr 7:16,916,359...17,346,152 		JBrowse link
G ALPP alkaline phosphatase, placental increases expression EXP alternariol results in increased expression of ALPP mRNA CTD PMID:32328700 NCBI chr 2:232,378,751...232,382,889
Ensembl chr 2:232,378,724...232,382,889 		JBrowse link
G AR androgen receptor decreases activity EXP alternariol results in decreased activity of AR protein CTD PMID:27481073 NCBI chr  X:67,544,021...67,730,619
Ensembl chr  X:67,544,021...67,730,619 		JBrowse link
G ARNT aryl hydrocarbon receptor nuclear translocator multiple interactions
affects response to substance		 ISO ARNT protein affects the reaction [alternariol results in increased expression of CYP1A1 protein]
ARNT protein affects the susceptibility to alternariol		 CTD PMID:22120949 NCBI chr 1:150,809,713...150,876,599
Ensembl chr 1:150,809,713...150,876,708 		JBrowse link
G CASP3 caspase 3 increases activity EXP alternariol results in increased activity of CASP3 protein CTD PMID:22542754 NCBI chr 4:184,627,696...184,649,447
Ensembl chr 4:184,627,696...184,650,062 		JBrowse link
G CASP9 caspase 9 increases activity EXP alternariol results in increased activity of CASP9 protein CTD PMID:22542754 NCBI chr 1:15,491,401...15,524,912
Ensembl chr 1:15,490,832...15,526,534 		JBrowse link
G CCND1 cyclin D1 multiple interactions
increases expression		 ISO 6-isopropoxy-9-oxoxanthene-2-carboxylic acid inhibits the reaction [alternariol results in increased expression of CCND1 protein]; butaprost promotes the reaction [alternariol results in increased expression of CCND1 protein] CTD PMID:30503586 NCBI chr11:69,641,156...69,654,474
Ensembl chr11:69,641,156...69,654,474 		JBrowse link
G CD68 CD68 molecule increases expression EXP alternariol results in increased expression of CD68 protein CTD PMID:26341179 NCBI chr17:7,579,638...7,582,111
Ensembl chr17:7,579,491...7,582,111 		JBrowse link
G CD83 CD83 molecule increases expression EXP
ISO		 alternariol results in increased expression of CD83 protein CTD PMID:26341179 NCBI chr 6:14,117,256...14,136,918
Ensembl chr 6:14,117,256...14,136,918 		JBrowse link
G CD86 CD86 molecule increases expression EXP
ISO		 alternariol results in increased expression of CD86 protein CTD PMID:26341179 NCBI chr 3:122,055,362...122,121,136
Ensembl chr 3:122,055,362...122,121,139 		JBrowse link
G CREB1 cAMP responsive element binding protein 1 increases expression
multiple interactions		 ISO alternariol results in increased expression of CREB1 protein modified form
6-isopropoxy-9-oxoxanthene-2-carboxylic acid inhibits the reaction [alternariol results in increased expression of CREB1 protein modified form]; N-(2-(4-bromocinnamylamino)ethyl)-5-isoquinolinesulfonamide inhibits the reaction [alternariol results in increased expression of CREB1 protein modified form]		 CTD PMID:30503586 NCBI chr 2:207,529,962...207,605,988
Ensembl chr 2:207,529,737...207,605,988 		JBrowse link
G CSNK2A1 casein kinase 2 alpha 1 decreases activity EXP alternariol results in decreased activity of CSNK2A1 protein CTD PMID:32328700 NCBI chr20:472,498...543,790
Ensembl chr20:472,498...543,835 		JBrowse link
G CXCL8 C-X-C motif chemokine ligand 8 multiple interactions EXP [altertoxin II co-treated with alternariol] affects the reaction [IL1B protein affects the expression of CXCL8 mRNA]; alternariol affects the reaction [altertoxin II affects the reaction [IL1B protein affects the secretion of CXCL8 protein]]; alternariol affects the reaction [IL1B protein affects the expression of CXCL8 mRNA]; alternariol affects the reaction [IL1B protein affects the secretion of CXCL8 protein]; altertoxin II affects the reaction [alternariol affects the reaction [IL1B protein affects the secretion of CXCL8 protein]] CTD PMID:35405071 NCBI chr 4:73,740,569...73,743,716
Ensembl chr 4:73,740,519...73,743,716 		JBrowse link
G CYP11B2 cytochrome P450 family 11 subfamily B member 2 increases expression EXP alternariol results in increased expression of CYP11B2 mRNA CTD PMID:23665424 NCBI chr 8:142,910,559...142,917,843
Ensembl chr 8:142,910,559...142,917,843 		JBrowse link
G CYP17A1 cytochrome P450 family 17 subfamily A member 1 increases expression EXP alternariol results in increased expression of CYP17A1 mRNA CTD PMID:23665424 NCBI chr10:102,830,531...102,837,413
Ensembl chr10:102,830,531...102,837,472 		JBrowse link
G CYP19A1 cytochrome P450 family 19 subfamily A member 1 increases expression EXP alternariol results in increased expression of CYP19A1 mRNA CTD PMID:23665424 NCBI chr15:51,208,057...51,338,596
Ensembl chr15:51,208,057...51,338,601 		JBrowse link
G CYP1A1 cytochrome P450 family 1 subfamily A member 1 multiple interactions
affects expression
affects activity
increases expression		 ISO
EXP		 AHR protein affects the reaction [alternariol results in increased expression of CYP1A1 protein]; ARNT protein affects the reaction [alternariol results in increased expression of CYP1A1 protein]
alternariol affects the expression of CYP1A1 mRNA
alternariol affects the activity of CYP1A1 protein
alternariol results in increased expression of CYP1A1 mRNA		 CTD PMID:22120949 PMID:23665424 PMID:26474839 NCBI chr15:74,719,542...74,725,528
Ensembl chr15:74,719,542...74,725,536 		JBrowse link
G GSR glutathione-disulfide reductase decreases activity EXP alternariol results in decreased activity of GSR protein CTD PMID:25827405 NCBI chr 8:30,678,066...30,727,846
Ensembl chr 8:30,678,066...30,727,846 		JBrowse link
G GSTA1 glutathione S-transferase alpha 1 affects localization EXP alternariol affects the localization of GSTA1 mRNA CTD PMID:23154127 NCBI chr 6:52,791,371...52,803,816
Ensembl chr 6:52,791,371...52,803,860 		JBrowse link
G GSTA2 glutathione S-transferase alpha 2 affects localization EXP alternariol affects the localization of GSTA2 mRNA CTD PMID:23154127 NCBI chr 6:52,750,087...52,763,475
Ensembl chr 6:52,750,087...52,763,475 		JBrowse link
G H2AX H2A.X variant histone increases expression EXP alternariol results in increased expression of H2AX protein modified form CTD PMID:26341179 NCBI chr11:119,093,874...119,095,465
Ensembl chr11:119,093,874...119,095,465 		JBrowse link
G HSD3B2 hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 2 increases expression EXP alternariol results in increased expression of HSD3B2 mRNA CTD PMID:23665424 NCBI chr 1:119,414,931...119,423,034
Ensembl chr 1:119,414,931...119,423,035 		JBrowse link
G IL1B interleukin 1 beta multiple interactions EXP 2-methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazophenyl)amide affects the reaction [[alternariol co-treated with altertoxin II] affects the reaction [IL1B protein affects the expression of ITGB1 mRNA]]; 2-methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazophenyl)amide affects the reaction [alternariol affects the reaction [IL1B protein affects the expression of ITGB1 mRNA]]; [alternariol co-treated with altertoxin II] affects the reaction [IL1B protein affects the expression of ITGB1 mRNA]; [alternariol co-treated with altertoxin II] affects the reaction [IL1B protein affects the expression of MMP9 mRNA]; [alternariol co-treated with altertoxin II] affects the reaction [IL1B protein affects the expression of TJP1 mRNA]; [alternariol co-treated with altertoxin II] affects the reaction [IL1B protein affects the expression of TJP1 protein]; [alternariol co-treated with altertoxin II] promotes the reaction [IL1B protein affects the localization of AHR protein]; [altertoxin II co-treated with alternariol] affects the reaction [IL1B protein affects the expression of CXCL8 mRNA]; [altertoxin II co-treated with alternariol] affects the reaction [IL1B protein affects the expression of TNF mRNA]; alternariol affects the reaction [altertoxin II affects the reaction [IL1B protein affects the secretion of CXCL8 protein]]; alternariol affects the reaction [IL1B protein affects the expression of CXCL8 mRNA]; alternariol affects the reaction [IL1B protein affects the expression of ITGB1 mRNA]; alternariol affects the reaction [IL1B protein affects the expression of MMP2 mRNA]; alternariol affects the reaction [IL1B protein affects the expression of MMP9 mRNA]; alternariol affects the reaction [IL1B protein affects the expression of TNF mRNA]; alternariol affects the reaction [IL1B protein affects the secretion of CXCL8 protein]; alternariol inhibits the reaction [IL1B protein affects the localization of RELA protein]; alternariol promotes the reaction [IL1B protein affects the localization of AHR protein]; altertoxin II affects the reaction [alternariol affects the reaction [IL1B protein affects the expression of MMP2 mRNA]]; altertoxin II affects the reaction [alternariol affects the reaction [IL1B protein affects the secretion of CXCL8 protein]] CTD PMID:35405071 NCBI chr 2:112,829,751...112,836,779
Ensembl chr 2:112,829,751...112,836,816 		JBrowse link
G IL6 interleukin 6 increases expression
increases secretion		 ISO
EXP		 alternariol results in increased expression of IL6 mRNA
alternariol results in increased secretion of IL6 protein		 CTD PMID:26341179 NCBI chr 7:22,727,200...22,731,998
Ensembl chr 7:22,725,884...22,732,002 		JBrowse link
G ITGAM integrin subunit alpha M increases expression ISO alternariol results in increased expression of ITGAM protein CTD PMID:26341179 NCBI chr16:31,259,975...31,332,877
Ensembl chr16:31,259,967...31,332,892 		JBrowse link
G ITGB1 integrin subunit beta 1 multiple interactions EXP 2-methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazophenyl)amide affects the reaction [[alternariol co-treated with altertoxin II] affects the reaction [IL1B protein affects the expression of ITGB1 mRNA]]; 2-methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazophenyl)amide affects the reaction [alternariol affects the reaction [IL1B protein affects the expression of ITGB1 mRNA]]; [alternariol co-treated with altertoxin II] affects the reaction [IL1B protein affects the expression of ITGB1 mRNA]; alternariol affects the reaction [IL1B protein affects the expression of ITGB1 mRNA] CTD PMID:35405071 NCBI chr10:32,900,318...32,958,230
Ensembl chr10:32,887,273...33,005,792 		JBrowse link
G MC2R melanocortin 2 receptor increases expression EXP alternariol results in increased expression of MC2R mRNA CTD PMID:23665424 NCBI chr18:13,882,044...13,915,707
Ensembl chr18:13,882,044...13,915,707 		JBrowse link
G MIR192 microRNA 192 multiple interactions EXP [altertoxin II co-treated with alternariol] results in decreased expression of MIR192 mRNA CTD PMID:28007639 NCBI chr11:64,891,137...64,891,246
Ensembl chr11:64,891,137...64,891,246 		JBrowse link
G MIR224 microRNA 224 multiple interactions EXP [altertoxin II co-treated with alternariol] results in increased expression of MIR224 mRNA CTD PMID:28007639 NCBI chr  X:151,958,578...151,958,658
Ensembl chr  X:151,958,578...151,958,658 		JBrowse link
G MIR29A microRNA 29a increases expression EXP alternariol results in increased expression of MIR29A mRNA CTD PMID:28007639 NCBI chr 7:130,876,747...130,876,810
Ensembl chr 7:130,876,747...130,876,810 		JBrowse link
G MIR4654 microRNA 4654 increases expression EXP alternariol results in increased expression of MIR4654 mRNA CTD PMID:28007639 NCBI chr 1:162,157,107...162,157,182
Ensembl chr 1:162,157,107...162,157,182 		JBrowse link
G MIR4715 microRNA 4715 increases expression EXP alternariol results in increased expression of MIR4715 mRNA CTD PMID:28007639 NCBI chr15:25,848,747...25,848,825
Ensembl chr15:25,848,747...25,848,825 		JBrowse link
G MIR6720 microRNA 6720 increases expression EXP alternariol results in increased expression of MIR6720 mRNA CTD PMID:28007639 NCBI chr 6:1,390,314...1,390,411
Ensembl chr 6:1,390,314...1,390,411 		JBrowse link
G MMP2 matrix metallopeptidase 2 multiple interactions EXP alternariol affects the reaction [IL1B protein affects the expression of MMP2 mRNA]; altertoxin II affects the reaction [alternariol affects the reaction [IL1B protein affects the expression of MMP2 mRNA]] CTD PMID:35405071 NCBI chr16:55,478,830...55,506,691
Ensembl chr16:55,389,700...55,506,691 		JBrowse link
G MMP9 matrix metallopeptidase 9 multiple interactions EXP [alternariol co-treated with altertoxin II] affects the reaction [IL1B protein affects the expression of MMP9 mRNA]; alternariol affects the reaction [IL1B protein affects the expression of MMP9 mRNA] CTD PMID:35405071 NCBI chr20:46,008,908...46,016,561
Ensembl chr20:46,008,908...46,016,561 		JBrowse link
G MTOR mechanistic target of rapamycin kinase decreases phosphorylation ISO alternariol results in decreased phosphorylation of MTOR protein CTD PMID:25456271 NCBI chr 1:11,106,535...11,262,551
Ensembl chr 1:11,106,535...11,262,556 		JBrowse link
G NFE2L2 NFE2 like bZIP transcription factor 2 affects localization
multiple interactions		 EXP alternariol affects the localization of NFE2L2 protein
2-methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazophenyl)amide inhibits the reaction [[alternariol co-treated with altertoxin II] affects the localization of NFE2L2 protein]; 2-methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazophenyl)amide inhibits the reaction [alternariol affects the localization of NFE2L2 protein]; [alternariol co-treated with altertoxin II] affects the localization of NFE2L2 protein		 CTD PMID:23154127 PMID:35405071 NCBI chr 2:177,230,303...177,264,727
Ensembl chr 2:177,218,667...177,392,756 		JBrowse link
G NR0B1 nuclear receptor subfamily 0 group B member 1 decreases expression EXP alternariol results in decreased expression of NR0B1 mRNA CTD PMID:23665424 NCBI chr  X:30,304,206...30,309,390
Ensembl chr  X:30,304,206...30,309,390 		JBrowse link
G PGR progesterone receptor increases expression
multiple interactions		 EXP alternariol results in increased expression of PGR protein
fulvestrant inhibits the reaction [alternariol results in increased expression of PGR protein]		 CTD PMID:23665424 NCBI chr11:101,029,624...101,129,813
Ensembl chr11:101,029,624...101,129,813 		JBrowse link
G PTGER2 prostaglandin E receptor 2 increases expression
multiple interactions		 ISO alternariol results in increased expression of PTGER2 protein
6-isopropoxy-9-oxoxanthene-2-carboxylic acid inhibits the reaction [alternariol results in increased expression of PTGER2 protein]; butaprost promotes the reaction [alternariol results in increased expression of PTGER2 protein]		 CTD PMID:30503586 NCBI chr14:52,314,312...52,328,598
Ensembl chr14:52,314,305...52,328,598 		JBrowse link
G PTGER4 prostaglandin E receptor 4 multiple interactions
increases expression		 ISO L-161982 inhibits the reaction [alternariol results in increased expression of PTGER4 protein] CTD PMID:30503586 NCBI chr 5:40,679,915...40,746,800
Ensembl chr 5:40,679,915...40,693,735 		JBrowse link
G PTGS2 prostaglandin-endoperoxide synthase 2 increases expression
multiple interactions		 ISO alternariol results in increased expression of PTGS2 protein
6-isopropoxy-9-oxoxanthene-2-carboxylic acid inhibits the reaction [alternariol results in increased expression of PTGS2 protein]; butaprost promotes the reaction [alternariol results in increased expression of PTGS2 protein]		 CTD PMID:30503586 NCBI chr 1:186,671,791...186,680,423
Ensembl chr 1:186,671,791...186,680,922 		JBrowse link
G RELA RELA proto-oncogene, NF-kB subunit multiple interactions EXP alternariol inhibits the reaction [IL1B protein affects the localization of RELA protein] CTD PMID:35405071 NCBI chr11:65,653,601...65,663,857
Ensembl chr11:65,653,599...65,663,090 		JBrowse link
G RPS6KB1 ribosomal protein S6 kinase B1 decreases phosphorylation ISO alternariol results in decreased phosphorylation of RPS6KB1 protein CTD PMID:25456271 NCBI chr17:59,893,121...59,950,574
Ensembl chr17:59,893,046...59,950,574 		JBrowse link
G SESN2 sestrin 2 increases expression ISO alternariol results in increased expression of SESN2 protein CTD PMID:25456271 NCBI chr 1:28,259,518...28,282,491
Ensembl chr 1:28,259,518...28,282,491 		JBrowse link
G TJP1 tight junction protein 1 multiple interactions EXP [alternariol co-treated with altertoxin II] affects the reaction [IL1B protein affects the expression of TJP1 mRNA]; [alternariol co-treated with altertoxin II] affects the reaction [IL1B protein affects the expression of TJP1 protein]; [alternariol co-treated with altertoxin II] results in increased expression of TJP1 protein CTD PMID:35405071 NCBI chr15:29,699,367...29,969,049
Ensembl chr15:29,699,367...29,968,915 		JBrowse link
G TNF tumor necrosis factor increases secretion
multiple interactions
increases expression		 EXP
ISO		 alternariol results in increased secretion of TNF protein
[altertoxin II co-treated with alternariol] affects the reaction [IL1B protein affects the expression of TNF mRNA]; alternariol affects the reaction [IL1B protein affects the expression of TNF mRNA]
alternariol results in increased expression of TNF mRNA		 CTD PMID:26341179 PMID:35405071 NCBI chr 6:31,575,565...31,578,336
Ensembl chr 6:31,575,565...31,578,336 		JBrowse link
G TOP2A DNA topoisomerase II alpha decreases activity EXP alternariol metabolite results in decreased activity of TOP2A protein; alternariol results in decreased activity of TOP2A protein CTD PMID:27422292 PMID:27682608 NCBI chr17:40,388,525...40,417,896
Ensembl chr17:40,388,525...40,417,896 		JBrowse link
G TOP2B DNA topoisomerase II beta decreases activity EXP alternariol metabolite results in decreased activity of TOP2B protein; alternariol results in decreased activity of TOP2B protein CTD PMID:27422292 NCBI chr 3:25,597,905...25,664,907
Ensembl chr 3:25,597,978...25,664,909 		JBrowse link
G TP53 tumor protein p53 increases expression EXP alternariol results in increased expression of TP53 protein CTD PMID:22542754 NCBI chr17:7,668,421...7,687,490
Ensembl chr17:7,661,779...7,687,546 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 26040
    role 25956
      biological role 25935
        biochemical role 25168
          metabolite 25098
            alternariol 50
              alternariol hapten ALa 0
              alternariol hapten ALb 0
              djalonensone 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 26040
    subatomic particle 26015
      composite particle 26015
        hadron 26015
          baryon 26015
            nucleon 26015
              atomic nucleus 26015
                atom 26015
                  main group element atom 25840
                    p-block element atom 25840
                      carbon group element atom 25437
                        carbon atom 25395
                          organic molecular entity 25395
                            organic molecule 25223
                              organic cyclic compound 24277
                                organic heterocyclic compound 22320
                                  organic heteropolycyclic compound 21317
                                    organic heterotricyclic compound 15971
                                      benzochromene 96
                                        benzochromenone 70
                                          alternariol 50
                                            alternariol hapten ALa 0
                                            alternariol hapten ALb 0
                                            djalonensone 0
paths to the root