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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;   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: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]
CTD PMID:22120949 NCBI chr 6:54,963,990...55,001,806
Ensembl chr 6:54,963,990...55,001,464
JBrowse link
G Alpp alkaline phosphatase, placental increases expression ISO alternariol results in increased expression of ALPP mRNA CTD PMID:32328700 NCBI chr 9:94,189,961...94,193,054
Ensembl chr 9:94,190,067...94,192,813
JBrowse link
G Ar androgen receptor decreases activity ISO alternariol results in decreased activity of AR protein CTD PMID:27481073 NCBI chr  X:67,656,253...67,828,998
Ensembl chr  X:67,656,253...67,829,026
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 2:196,594,178...196,651,486
Ensembl chr 2:196,594,303...196,651,179
JBrowse link
G Casp3 caspase 3 increases activity ISO alternariol results in increased activity of CASP3 protein CTD PMID:22542754 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Casp9 caspase 9 increases activity ISO alternariol results in increased activity of CASP9 protein CTD PMID:22542754 NCBI chr 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778
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 1:218,090,750...218,100,447
Ensembl chr 1:218,090,750...218,100,325
JBrowse link
G Cd68 Cd68 molecule increases expression ISO alternariol results in increased expression of CD68 protein CTD PMID:26341179 NCBI chr10:56,268,726...56,270,605
Ensembl chr10:56,268,720...56,270,640
JBrowse link
G Cd83 CD83 molecule increases expression ISO alternariol results in increased expression of CD83 protein CTD PMID:26341179 NCBI chr17:24,416,651...24,435,790
Ensembl chr17:24,416,651...24,435,790
JBrowse link
G Cd86 CD86 molecule increases expression ISO alternariol results in increased expression of CD86 protein CTD PMID:26341179 NCBI chr11:67,060,305...67,117,990
Ensembl chr11:67,082,193...67,118,795
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 9:71,229,753...71,298,994
Ensembl chr 9:71,230,108...71,293,435
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 3:147,713,808...147,760,375
Ensembl chr 3:147,713,821...147,757,862
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 7:116,155,928...116,161,781
Ensembl chr 7:116,156,219...116,255,167
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 1:266,422,127...266,429,947
Ensembl chr 1:266,422,132...266,428,239
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 8:58,744,849...58,772,408
Ensembl chr 8:58,744,849...58,772,408
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions
affects expression
affects activity
increases 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 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 chr 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
JBrowse link
G Gsr glutathione-disulfide reductase decreases activity ISO alternariol results in decreased activity of GSR protein CTD PMID:25827405 NCBI chr16:62,197,617...62,239,987
Ensembl chr16:62,197,617...62,241,361
JBrowse link
G Gsta1 glutathione S-transferase alpha 1 affects localization ISO alternariol affects the localization of GSTA1 mRNA CTD PMID:23154127 NCBI chr 9:27,366,404...27,381,004
Ensembl chr 9:27,368,272...27,452,902
JBrowse link
G Gsta2 glutathione S-transferase alpha 2 affects localization ISO alternariol affects the localization of GSTA2 mRNA CTD PMID:23154127 NCBI chr 8:85,640,081...85,645,621 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 8:48,665,652...48,666,981
Ensembl chr 8:48,665,652...48,666,981
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 2:200,712,895...200,722,429
Ensembl chr 2:202,341,422...202,350,929
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 4:3,043,231...3,047,807
Ensembl chr 4:3,043,231...3,047,807
JBrowse link
G Itgam integrin subunit alpha M increases expression ISO alternariol results in increased expression of ITGAM protein CTD PMID:26341179 NCBI chr 1:199,495,312...199,545,738
Ensembl chr 1:199,495,298...199,623,960
JBrowse link
G Mc2r melanocortin 2 receptor increases expression ISO alternariol results in increased expression of MC2R mRNA CTD PMID:23665424 NCBI chr18:64,166,959...64,178,729
Ensembl chr18:64,167,191...64,177,729
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 1:221,634,971...221,635,080
Ensembl chr 1:221,634,971...221,635,080
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:152,223,754...152,223,835
Ensembl chr  X:152,223,754...152,223,835
JBrowse link
G Mir29a microRNA 29a increases expression ISO alternariol results in increased expression of MIR29A mRNA CTD PMID:28007639 NCBI chr 4:58,343,931...58,344,018 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 5:165,263,813...165,373,967
Ensembl chr 5:165,263,800...165,373,967
JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 affects localization ISO alternariol affects the localization of NFE2L2 protein CTD PMID:23154127 NCBI chr 3:62,497,568...62,525,146
Ensembl chr 3:62,497,571...62,524,996
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:54,734,385...54,738,513
Ensembl chr  X:54,734,385...54,738,513
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 8:7,128,656...7,187,796
Ensembl chr 8:7,128,656...7,187,796
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 chr15:19,336,029...19,349,759
Ensembl chr15:19,338,175...19,350,210
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 2:54,951,625...54,966,470
Ensembl chr 2:54,952,821...54,963,448
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 chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
JBrowse link
G Rps6kb1 ribosomal protein S6 kinase B1 decreases phosphorylation ISO alternariol results in decreased phosphorylation of RPS6KB1 protein CTD PMID:25456271 NCBI chr10:73,824,200...73,865,503
Ensembl chr10:73,824,202...73,865,364
JBrowse link
G Sesn2 sestrin 2 increases expression ISO alternariol results in increased expression of SESN2 protein CTD PMID:25456271 NCBI chr 5:150,684,891...150,703,846
Ensembl chr 5:150,684,133...150,704,117
JBrowse link
G Tnf tumor necrosis factor increases secretion
increases expression
ISO alternariol results in increased secretion of TNF protein
alternariol results in increased expression of TNF mRNA
CTD PMID:26341179 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
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 chr10:86,901,467...86,930,947
Ensembl chr10:86,901,007...86,932,154
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 chr15:10,262,972...10,319,741
Ensembl chr15:10,262,651...10,320,233
JBrowse link
G Tp53 tumor protein p53 increases expression ISO alternariol results in increased expression of TP53 protein CTD PMID:22542754 NCBI chr10:56,186,299...56,198,449
Ensembl chr10:56,187,020...56,198,449
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19816
    role 19764
      biological role 19764
        biochemical role 19313
          metabolite 19294
            alternariol 40
              djalonensone 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic molecule 19522
                              organic cyclic compound 19320
                                organic heterocyclic compound 18432
                                  organic heteropolycyclic compound 17844
                                    organic heterotricyclic compound 14583
                                      benzochromene 70
                                        benzochromenone 56
                                          alternariol 40
                                            djalonensone 0
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.