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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 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 6:57,961,423...57,998,901
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 9:95,213,763...95,216,509
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:67,135,317...67,304,476
Ensembl chr  X:63,104,771...63,273,925 		JBrowse link
G Arnt aryl hydrocarbon receptor nuclear translocator affects response to substance
multiple interactions		 ISO ARNT protein affects the susceptibility to alternariol
ARNT protein affects the reaction [alternariol results in increased expression of CYP1A1 protein]		 CTD PMID:22120949 NCBI chr 2:185,686,703...185,745,546
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 chr16:52,395,539...52,413,794
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 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 1:209,518,288...209,527,986
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 chr10:54,880,562...54,882,441
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 chr17:21,093,281...21,113,223
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 chr11:77,647,565...77,706,178
Ensembl chr11:64,163,828...64,200,818 		JBrowse link
G Creb1 cAMP responsive element binding protein 1 multiple interactions
increases expression		 ISO 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 9:73,397,333...73,466,339
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 3:161,170,295...161,217,073
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 7:108,689,319...108,694,808
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 1:255,476,861...255,484,547
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 8:63,449,148...63,476,534
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 expression
affects activity		 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 expression of CYP1A1 mRNA
alternariol affects the activity of CYP1A1 protein		 CTD PMID:22120949 PMID:23665424 PMID:26474839 NCBI chr 8:66,991,940...66,998,014
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 chr16:65,185,574...65,228,742
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 9:31,199,887...31,216,606
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 8:88,064,829...88,077,168
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 8:53,568,718...53,570,072
Ensembl chr 8:44,671,786...44,673,239
Ensembl chr 4:44,671,786...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 2:188,784,614...188,812,535
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 3:137,030,200...137,036,581
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Il6 interleukin 6 increases secretion
increases expression		 ISO alternariol results in increased secretion of IL6 protein
alternariol results in increased expression of IL6 mRNA		 CTD PMID:26341179 NCBI chr 4:5,889,999...5,894,575
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 1:192,089,496...192,139,947
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 chr19:73,602,277...73,650,271
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 chr18:64,279,878...64,291,775
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 1:212,994,209...212,994,318
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:155,107,130...155,107,211
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 4:60,617,955...60,618,042 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 chr19:30,327,643...30,355,856
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 3:174,103,474...174,111,434
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 5:164,167,985...164,277,438
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 3:81,001,529...81,031,165
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:54,707,658...54,711,786
Ensembl chr  X:50,756,886...50,761,011 		JBrowse link
G Pgr progesterone receptor multiple interactions
increases expression		 ISO fulvestrant inhibits the reaction [alternariol results in increased expression of PGR protein] CTD PMID:23665424 NCBI chr 8:14,354,398...14,413,271
Ensembl chr 8:6,072,673...6,131,344 		JBrowse link
G Ptger2 prostaglandin E receptor 2 multiple interactions
increases expression		 ISO 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 chr15:20,694,765...20,708,475
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 2:56,061,699...56,074,594
Ensembl chr 2:54,335,424...54,346,670 		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 chr13:64,714,063...64,722,320
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 1:212,354,336...212,364,815
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 chr10:71,817,794...71,865,211
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 5:149,986,304...150,005,255
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 1:128,260,330...128,505,018
Ensembl chr 1:118,849,838...119,094,432 		JBrowse link
G Tnf tumor necrosis factor increases expression
increases secretion
multiple interactions		 ISO alternariol results in increased expression of TNF mRNA
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]		 CTD PMID:26341179 PMID:35405071 NCBI chr20:3,626,685...3,629,303
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 chr10:84,441,954...84,473,093
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 chr15:11,482,089...11,542,464
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 chr10:54,798,871...54,810,300
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 19909
    role 19880
      biological role 19878
        biochemical role 19586
          metabolite 19573
            alternariol 46
              alternariol hapten ALa 0
              alternariol hapten ALb 0
              djalonensone 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19909
    subatomic particle 19907
      composite particle 19907
        hadron 19907
          baryon 19907
            nucleon 19907
              atomic nucleus 19907
                atom 19907
                  main group element atom 19846
                    p-block element atom 19846
                      carbon group element atom 19784
                        carbon atom 19781
                          organic molecular entity 19781
                            organic molecule 19735
                              organic cyclic compound 19528
                                organic heterocyclic compound 18895
                                  organic heteropolycyclic compound 18318
                                    organic heterotricyclic compound 15880
                                      benzochromene 3270
                                        benzochromenone 3254
                                          alternariol 46
                                            alternariol hapten ALa 0
                                            alternariol hapten ALb 0
                                            djalonensone 0
paths to the root