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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



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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 AHR protein affects the susceptibility to alternariol
AHR protein affects the reaction [alternariol results in increased expression of CYP1A1 protein]
[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]
CTD PMID:22120949 PMID:35405071 NCBI chr 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568
JBrowse link
G Alpp alkaline phosphatase, placental increases expression ISO alternariol results in increased expression of ALPP mRNA CTD PMID:32328700 NCBI chr 9:87,765,846...87,768,606
Ensembl chr 9:87,765,860...87,768,606
JBrowse link
G Ar androgen receptor decreases activity ISO alternariol results in decreased activity of AR protein CTD PMID:27481073 NCBI chr  X:63,104,771...63,273,934
Ensembl chr  X:63,104,771...63,273,925
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 2:182,997,731...183,056,584
Ensembl chr 2:182,997,736...183,056,580
JBrowse link
G Casp3 caspase 3 increases activity ISO alternariol results in increased activity of CASP3 protein CTD PMID:22542754 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp9 caspase 9 increases activity ISO alternariol results in increased activity of CASP9 protein CTD PMID:22542754 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
JBrowse link
G Ccnd1 cyclin D1 increases expression
multiple interactions
ISO alternariol results in increased expression of CCND1 protein
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 chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602
JBrowse link
G Cd68 Cd68 molecule increases expression ISO alternariol results in increased expression of CD68 protein CTD PMID:26341179 NCBI chr10:54,381,814...54,383,693
Ensembl chr10:54,381,815...54,383,697
JBrowse link
G Cd83 CD83 molecule increases expression ISO alternariol results in increased expression of CD83 protein CTD PMID:26341179 NCBI chr17:20,887,309...20,907,009
Ensembl chr17:20,887,309...20,907,083
JBrowse link
G Cd86 CD86 molecule increases expression ISO alternariol results in increased expression of CD86 protein CTD PMID:26341179 NCBI chr11:64,142,193...64,200,816
Ensembl chr11:64,163,828...64,200,818
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 9:65,903,511...65,972,562
Ensembl chr 9:65,903,547...65,970,816
JBrowse link
G Csnk2a1 casein kinase 2 alpha 1 decreases activity ISO alternariol results in decreased activity of CSNK2A1 protein CTD PMID:32328700 NCBI chr 3:140,709,984...140,756,757
Ensembl chr 3:140,709,991...140,756,696
JBrowse link
G Cyp11b3 cytochrome P450, family 11, subfamily b, polypeptide 3 increases expression ISO alternariol results in increased expression of CYP11B2 mRNA CTD PMID:23665424 NCBI chr 7:106,808,559...106,814,048
Ensembl chr 7:106,808,559...106,814,048
JBrowse link
G Cyp17a1 cytochrome P450, family 17, subfamily a, polypeptide 1 increases expression ISO alternariol results in increased expression of CYP17A1 mRNA CTD PMID:23665424 NCBI chr 1:245,535,462...245,543,148
Ensembl chr 1:245,535,462...245,541,573
JBrowse link
G Cyp19a1 cytochrome P450, family 19, subfamily a, polypeptide 1 increases expression ISO alternariol results in increased expression of CYP19A1 mRNA CTD PMID:23665424 NCBI chr 8:54,553,165...54,580,758
Ensembl chr 8:54,553,165...54,580,758
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions
increases expression
affects activity
affects expression
ISO 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 results in increased expression of CYP1A1 mRNA
alternariol affects the activity of CYP1A1 protein
alternariol affects the expression of CYP1A1 mRNA
CTD PMID:22120949 PMID:23665424 PMID:26474839 NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125
JBrowse link
G Gsr glutathione-disulfide reductase decreases activity ISO alternariol results in decreased activity of GSR protein CTD PMID:25827405 NCBI chr16:58,482,209...58,525,256
Ensembl chr16:58,482,505...58,525,661
JBrowse link
G Gsta1 glutathione S-transferase alpha 1 affects localization ISO alternariol affects the localization of GSTA1 mRNA CTD PMID:23154127 NCBI chr 9:23,703,476...23,720,121
Ensembl chr 9:23,703,477...23,720,121
JBrowse link
G Gsta2 glutathione S-transferase alpha 2 affects localization ISO alternariol affects the localization of GSTA2 mRNA CTD PMID:23154127 NCBI chr 8:79,184,535...79,196,827
Ensembl chr 8:79,184,322...79,196,798
JBrowse link
G H2ax H2A.X variant histone increases expression ISO alternariol results in increased expression of H2AX protein modified form CTD PMID:26341179 NCBI chr 8:44,671,927...44,673,257
Ensembl chr 8:44,671,786...44,673,239
JBrowse link
G Hsd3b2 hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 2 increases expression ISO alternariol results in increased expression of HSD3B2 mRNA CTD PMID:23665424 NCBI chr 2:186,095,897...186,105,354
Ensembl chr 2:186,095,897...186,101,852
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO 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 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415
JBrowse link
G Il6 interleukin 6 increases expression
increases secretion
ISO alternariol results in increased expression of IL6 mRNA
alternariol results in increased secretion of IL6 protein
CTD PMID:26341179 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Itgam integrin subunit alpha M increases expression ISO alternariol results in increased expression of ITGAM protein CTD PMID:26341179 NCBI chr 1:182,659,047...182,709,495
Ensembl chr 1:182,659,000...182,709,503
JBrowse link
G Itgb1 integrin subunit beta 1 multiple interactions ISO 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 chr19:56,705,123...56,753,199
Ensembl chr19:56,705,171...56,753,195
JBrowse link
G Mc2r melanocortin 2 receptor increases expression ISO alternariol results in increased expression of MC2R mRNA CTD PMID:23665424 NCBI chr18:62,001,980...62,015,567
Ensembl chr18:62,004,948...62,015,488
JBrowse link
G Mir192 microRNA 192 multiple interactions ISO [altertoxin II co-treated with alternariol] results in decreased expression of MIR192 mRNA CTD PMID:28007639 NCBI chr 1:203,564,946...203,565,055
Ensembl chr 1:203,564,946...203,565,055
JBrowse link
G Mir224 microRNA 224 multiple interactions ISO [altertoxin II co-treated with alternariol] results in increased expression of MIR224 mRNA CTD PMID:28007639 NCBI chr  X:150,065,088...150,065,169
Ensembl chr  X:150,065,088...150,065,169
JBrowse link
G Mir29a microRNA 29a increases expression ISO alternariol results in increased expression of MIR29A mRNA CTD PMID:28007639 NCBI chr 4:59,650,608...59,650,695 JBrowse link
G Mmp2 matrix metallopeptidase 2 multiple interactions ISO 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 chr19:14,154,657...14,182,870
Ensembl chr19:14,154,657...14,182,870
JBrowse link
G Mmp9 matrix metallopeptidase 9 multiple interactions ISO [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 chr 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120
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 5:158,884,856...158,994,311
Ensembl chr 5:158,884,804...158,994,311
JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 affects localization
multiple interactions
ISO 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 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737
JBrowse link
G Nr0b1 nuclear receptor subfamily 0, group B, member 1 decreases expression ISO alternariol results in decreased expression of NR0B1 mRNA CTD PMID:23665424 NCBI chr  X:50,756,886...50,761,014
Ensembl chr  X:50,756,886...50,761,011
JBrowse link
G Pgr progesterone receptor increases expression
multiple interactions
ISO alternariol results in increased expression of PGR protein
fulvestrant inhibits the reaction [alternariol results in increased expression of PGR protein]
CTD PMID:23665424 NCBI chr 8:6,073,216...6,131,552
Ensembl chr 8:6,072,673...6,131,344
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 chr15:18,215,013...18,228,714
Ensembl chr15:18,217,285...18,228,714
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 2:54,330,563...54,347,451
Ensembl chr 2:54,335,424...54,346,670
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions
increases expression
ISO 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 chr13:62,164,080...62,169,770
Ensembl chr13:62,163,932...62,172,188
JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions ISO alternariol inhibits the reaction [IL1B protein affects the localization of RELA protein] CTD PMID:35405071 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484
JBrowse link
G Rps6kb1 ribosomal protein S6 kinase B1 decreases phosphorylation ISO alternariol results in decreased phosphorylation of RPS6KB1 protein CTD PMID:25456271 NCBI chr10:71,323,777...71,367,908
Ensembl chr10:71,323,777...71,367,908
JBrowse link
G Sesn2 sestrin 2 increases expression ISO alternariol results in increased expression of SESN2 protein CTD PMID:25456271 NCBI chr 5:144,702,287...144,721,241
Ensembl chr 5:144,701,530...144,721,260
JBrowse link
G Tjp1 tight junction protein 1 multiple interactions ISO [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 chr 1:118,849,838...119,094,492
Ensembl chr 1:118,849,838...119,094,432
JBrowse link
G Tnf tumor necrosis factor increases secretion
increases expression
multiple interactions
ISO alternariol results in increased secretion of TNF protein
alternariol results in increased expression of TNF mRNA
[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]
CTD PMID:26341179 PMID:35405071 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Top2a DNA topoisomerase II alpha decreases activity ISO alternariol metabolite results in decreased activity of TOP2A protein; alternariol results in decreased activity of TOP2A protein CTD PMID:27422292 PMID:27682608 NCBI chr10:83,946,186...83,975,694
Ensembl chr10:83,945,735...83,976,874
JBrowse link
G Top2b DNA topoisomerase II beta decreases activity ISO alternariol metabolite results in decreased activity of TOP2B protein; alternariol results in decreased activity of TOP2B protein CTD PMID:27422292 NCBI chr15:9,051,661...9,111,220
Ensembl chr15:9,051,341...9,112,085
JBrowse link
G Tp53 tumor protein p53 increases expression ISO alternariol results in increased expression of TP53 protein CTD PMID:22542754 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19740
    role 19713
      biological role 19711
        biochemical role 19429
          metabolite 19416
            alternariol 46
              alternariol hapten ALa 0
              alternariol hapten ALb 0
              djalonensone 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19740
    subatomic particle 19738
      composite particle 19738
        hadron 19738
          baryon 19738
            nucleon 19738
              atomic nucleus 19738
                atom 19738
                  main group element atom 19686
                    p-block element atom 19686
                      carbon group element atom 19631
                        carbon atom 19627
                          organic molecular entity 19627
                            organic molecule 19587
                              organic cyclic compound 19393
                                organic heterocyclic compound 18766
                                  organic heteropolycyclic compound 18254
                                    organic heterotricyclic compound 15619
                                      benzochromene 87
                                        benzochromenone 61
                                          alternariol 46
                                            alternariol hapten ALa 0
                                            alternariol hapten ALb 0
                                            djalonensone 0
paths to the root