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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:butane-2,3-dione
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Accession:CHEBI:16583 term browser browse the term
Definition:An alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation.
Synonyms:related_synonym: 2,3-Butadione;   2,3-Butanedione;   2,3-Diketobutane;   2,3-Dioxobutane;   2,3-butandione;   Biacetyl;   Dimethyl glyoxal;   Dimethylglyoxal;   Formula=C4H6O2;   InChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3;   InChIKey=QSJXEFYPDANLFS-UHFFFAOYSA-N;   SMILES=CC(=O)C(C)=O;   diacetyl
 alt_id: CHEBI:14134;   CHEBI:4479
 xref: Beilstein:605398;   CAS:431-03-8;   HMDB:HMDB0003407;   KEGG:C00741
 xref_mesh: MESH:D003931
 xref: PMID:15654607;   PMID:24614328;   Reaxys:605398


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butane-2,3-dione term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Akr1b1 aldo-keto reductase family 1 member B increases reduction
multiple interactions
ISO AKR1B1 protein results in increased reduction of Diacetyl
[AKR1B1 protein results in increased reduction of Diacetyl] which results in increased chemical synthesis of Acetoin
CTD PMID:23295224 NCBI chr 4:61,706,866...61,720,959
Ensembl chr 4:61,706,864...61,720,956
JBrowse link
G Akr1b10 aldo-keto reductase family 1 member B10 increases reduction
multiple interactions
ISO AKR1B10 protein results in increased reduction of Diacetyl
[AKR1B10 protein results in increased reduction of Diacetyl] which results in increased chemical synthesis of Acetoin
CTD PMID:23295224 NCBI chr 4:61,813,265...61,830,371
Ensembl chr 4:61,771,970...61,828,657
JBrowse link
G Akr1b8 aldo-keto reductase family 1, member B8 multiple interactions EXP [AKR1B8 protein co-treated with NADP] affects the reduction of Diacetyl CTD PMID:18845131 NCBI chr 4:61,772,064...61,784,637
Ensembl chr 4:61,771,970...61,828,657
JBrowse link
G Alb albumin affects binding ISO
EXP
Diacetyl binds to ALB protein CTD PMID:25559854 NCBI chr14:19,176,275...19,191,793
Ensembl chr14:19,176,277...19,191,863
JBrowse link
G Aldh1a3 aldehyde dehydrogenase 1 family, member A3 increases expression ISO Diacetyl results in increased expression of ALDH1A3 mRNA CTD PMID:30710127 NCBI chr 1:127,302,920...127,337,828
Ensembl chr 1:127,301,128...127,337,882
JBrowse link
G Areg amphiregulin increases secretion ISO Diacetyl results in increased secretion of AREG protein CTD PMID:30851105 PMID:31381966 NCBI chr14:18,521,921...18,531,179
Ensembl chr14:18,521,930...18,531,179
JBrowse link
G B3gat3 beta-1,3-glucuronyltransferase 3 decreases activity
multiple interactions
ISO Diacetyl results in decreased activity of B3GAT3 protein
Uridine Diphosphate Glucuronic Acid inhibits the reaction [Diacetyl results in decreased activity of B3GAT3 protein]
CTD PMID:11986319 NCBI chr 1:225,120,061...225,126,579
Ensembl chr 1:225,120,061...225,126,579
JBrowse link
G Cc2d2a coiled-coil and C2 domain containing 2A decreases expression ISO Diacetyl results in decreased expression of CC2D2A mRNA CTD PMID:30710127 NCBI chr14:71,895,128...71,979,452
Ensembl chr14:71,895,246...71,973,419
JBrowse link
G Cdc20b cell division cycle 20B decreases expression ISO Diacetyl results in decreased expression of CDC20B mRNA CTD PMID:30710127 NCBI chr 2:44,916,806...44,947,860 JBrowse link
G Cfap221 cilia and flagella associated protein 221 decreases expression ISO Diacetyl results in decreased expression of CFAP221 mRNA CTD PMID:30710127 NCBI chr13:35,952,808...36,024,371
Ensembl chr13:35,953,088...36,022,197
JBrowse link
G Cfap70 cilia and flagella associated protein 70 decreases expression ISO Diacetyl results in decreased expression of CFAP70 mRNA CTD PMID:30710127 NCBI chr15:4,285,049...4,350,707
Ensembl chr15:4,285,052...4,350,714
JBrowse link
G Cxcl1 C-X-C motif chemokine ligand 1 increases expression
multiple interactions
EXP Diacetyl results in increased expression of CXCL1 mRNA
Diacetyl results in increased expression of and results in increased secretion of CXCL1 protein
CTD PMID:25145656 PMID:30851105 NCBI chr14:18,743,678...18,745,457
Ensembl chr14:18,743,685...18,745,457
JBrowse link
G Dcxr dicarbonyl and L-xylulose reductase multiple interactions ISO 1,2-naphthoquinone inhibits the reaction [[[DCXR protein co-treated with NAD] results in increased reduction of Diacetyl] which results in increased chemical synthesis of Acetoin]; 1,4-naphthoquinone inhibits the reaction [[[DCXR protein co-treated with NAD] results in increased reduction of Diacetyl] which results in increased chemical synthesis of Acetoin]; 9,10-phenanthrenequinone inhibits the reaction [[[DCXR protein co-treated with NAD] results in increased reduction of Diacetyl] which results in increased chemical synthesis of Acetoin]; [[DCXR protein co-treated with NAD] results in increased reduction of Diacetyl] which results in increased chemical synthesis of Acetoin; [DCXR protein co-treated with NAD] results in increased reduction of Diacetyl; [DCXR protein co-treated with NADP] results in increased reduction of Diacetyl; Butyric Acid inhibits the reaction [[DCXR protein co-treated with NADP] results in increased reduction of Diacetyl]; Diacetyl inhibits the reaction [[DCXR protein results in increased metabolism of Vitamin K 3] which results in increased chemical synthesis of Superoxides]; Heptanoic Acids inhibits the reaction [[DCXR protein co-treated with NADP] results in increased reduction of Diacetyl]; hexanoic acid inhibits the reaction [[DCXR protein co-treated with NADP] results in increased reduction of Diacetyl]; Pentanoic Acids inhibits the reaction [[DCXR protein co-treated with NADP] results in increased reduction of Diacetyl]; Vitamin K 3 inhibits the reaction [[[DCXR protein co-treated with NAD] results in increased reduction of Diacetyl] which results in increased chemical synthesis of Acetoin] CTD PMID:28595002 NCBI chr10:109,906,119...109,909,696
Ensembl chr10:109,906,815...109,909,715
JBrowse link
G Dhrs9 dehydrogenase/reductase 9 increases expression ISO Diacetyl results in increased expression of DHRS9 mRNA CTD PMID:30710127 NCBI chr 3:55,623,671...55,645,883
Ensembl chr 3:55,623,634...55,648,325
JBrowse link
G Dnaaf1 dynein, axonemal, assembly factor 1 decreases expression ISO Diacetyl results in decreased expression of DNAAF1 mRNA CTD PMID:30710127 NCBI chr19:52,217,427...52,245,930
Ensembl chr19:52,217,984...52,245,929
JBrowse link
G Dnah12 dynein, axonemal, heavy chain 12 decreases expression ISO Diacetyl results in decreased expression of DNAH12 mRNA CTD PMID:30710127 NCBI chr16:2,377,218...2,534,130
Ensembl chr16:2,379,480...2,534,131
JBrowse link
G Dnah3 dynein, axonemal, heavy chain 3 decreases expression ISO Diacetyl results in decreased expression of DNAH3 mRNA CTD PMID:30710127 NCBI chr 1:189,708,985...189,865,431 JBrowse link
G Dnah6 dynein, axonemal, heavy chain 6 decreases expression ISO Diacetyl results in decreased expression of DNAH6 mRNA CTD PMID:30710127 NCBI chr 4:100,936,834...101,157,511
Ensembl chr 4:100,936,978...101,156,576
JBrowse link
G Dnai1 dynein, axonemal, intermediate chain 1 decreases expression ISO Diacetyl results in decreased expression of DNAI1 mRNA CTD PMID:30710127 NCBI chr 5:57,947,796...58,017,985
Ensembl chr 5:57,947,716...58,017,992
JBrowse link
G Egfr epidermal growth factor receptor multiple interactions
increases phosphorylation
ISO N-((2-(hydroxyaminocarbonyl)methyl)-4-methylpentanoyl)-3-(2'-naphthyl)alanylalanine, 2-aminoethylamide inhibits the reaction [Diacetyl results in increased phosphorylation of EGFR protein] CTD PMID:30851105 NCBI chr14:99,919,485...100,104,136
Ensembl chr14:99,919,485...100,098,796
JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit increases expression EXP Diacetyl results in increased expression of GCLC mRNA CTD PMID:25145656 NCBI chr 8:85,059,051...85,097,471
Ensembl chr 8:85,059,051...85,097,468
JBrowse link
G Gsta1 glutathione S-transferase alpha 1 increases expression ISO Diacetyl results in increased expression of GSTA1 mRNA CTD PMID:31381966 NCBI chr 9:27,366,404...27,381,004
Ensembl chr 9:27,368,272...27,452,902
JBrowse link
G Hbegf heparin-binding EGF-like growth factor increases secretion ISO Diacetyl results in increased secretion of HBEGF protein CTD PMID:30851105 NCBI chr18:29,330,302...29,340,185
Ensembl chr18:29,329,764...29,340,403
JBrowse link
G Hmox1 heme oxygenase 1 increases expression EXP Diacetyl results in increased expression of HMOX1 mRNA CTD PMID:25145656 NCBI chr19:14,508,634...14,515,455
Ensembl chr19:14,508,616...14,515,456
JBrowse link
G Il6 interleukin 6 affects expression
decreases expression
increases expression
ISO
EXP
Diacetyl analog affects the expression of IL6 mRNA
Diacetyl results in decreased expression of IL6 mRNA
Diacetyl results in increased expression of IL6 mRNA
CTD PMID:20200221 PMID:25145656 PMID:31381966 NCBI chr 4:3,043,231...3,047,807
Ensembl chr 4:3,043,231...3,047,807
JBrowse link
G Krt5 keratin 5 multiple interactions ISO benzyloxycarbonylleucyl-leucyl-leucine aldehyde affects the reaction [Diacetyl affects the expression of and affects the ubiquitination of KRT5 protein]; Diacetyl affects the expression of and affects the ubiquitination of KRT5 protein CTD PMID:32112875 NCBI chr 7:143,320,142...143,324,536
Ensembl chr 7:143,316,920...143,453,546
JBrowse link
G Macrod2 mono-ADP ribosylhydrolase 2 decreases expression ISO Diacetyl results in decreased expression of MACROD2 mRNA CTD PMID:30710127 NCBI chr 3:135,729,839...136,422,082 JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation
multiple interactions
ISO Diacetyl results in increased phosphorylation of MAPK1 protein
RTKI cpd inhibits the reaction [Diacetyl results in increased phosphorylation of MAPK1 protein]
CTD PMID:30851105 NCBI chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
JBrowse link
G Mapk3 mitogen activated protein kinase 3 increases phosphorylation
multiple interactions
ISO Diacetyl results in increased phosphorylation of MAPK3 protein
RTKI cpd inhibits the reaction [Diacetyl results in increased phosphorylation of MAPK3 protein]
CTD PMID:30851105 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Mmp9 matrix metallopeptidase 9 increases secretion
increases expression
ISO Diacetyl results in increased secretion of MMP9 protein
Diacetyl results in increased expression of MMP9 mRNA
CTD PMID:31381966 NCBI chr 3:161,413,410...161,421,473
Ensembl chr 3:161,413,298...161,421,520
JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 affects localization EXP Diacetyl affects the localization of NFE2L2 protein CTD PMID:25145656 NCBI chr 3:62,497,568...62,525,146
Ensembl chr 3:62,497,571...62,524,996
JBrowse link
G Nfkb1 nuclear factor kappa B subunit 1 increases expression ISO Diacetyl results in increased expression of NFKB1 mRNA CTD PMID:31381966 NCBI chr 2:240,773,520...240,890,053
Ensembl chr 2:240,773,456...240,866,689
JBrowse link
G Papss2 3'-phosphoadenosine 5'-phosphosulfate synthase 2 decreases expression ISO Diacetyl results in decreased expression of PAPSS2 mRNA CTD PMID:30710127 NCBI chr 1:251,145,264...251,230,716
Ensembl chr 1:251,145,253...251,230,715
JBrowse link
G Prom1 prominin 1 decreases expression ISO Diacetyl results in decreased expression of PROM1 mRNA CTD PMID:30710127 NCBI chr14:71,532,321...71,637,400
Ensembl chr14:71,533,063...71,637,417
JBrowse link
G Ptges2 prostaglandin E synthase 2 increases expression ISO Diacetyl results in increased expression of PTGES2 mRNA CTD PMID:31381966 NCBI chr 3:11,424,195...11,431,379
Ensembl chr 3:11,424,099...11,431,402
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 decreases expression ISO Diacetyl results in decreased expression of PTGS2 mRNA CTD PMID:30710127 NCBI chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
JBrowse link
G Pthlh parathyroid hormone-like hormone decreases expression ISO Diacetyl results in decreased expression of PTHLH mRNA CTD PMID:30710127 NCBI chr 4:181,663,425...181,674,181 JBrowse link
G Scgb1a1 secretoglobin family 1A member 1 decreases expression EXP Diacetyl results in decreased expression of SCGB1A1 protein CTD PMID:21464978 NCBI chr 1:225,279,698...225,283,246
Ensembl chr 1:225,279,676...225,283,326
JBrowse link
G Slpi secretory leukocyte peptidase inhibitor increases secretion
affects expression
ISO Diacetyl results in increased secretion of SLPI protein
Diacetyl affects the expression of SLPI mRNA
CTD PMID:31381966 NCBI chr 3:160,799,979...160,802,228
Ensembl chr 3:160,799,981...160,802,433
JBrowse link
G Sorcs2 sortilin-related VPS10 domain containing receptor 2 decreases expression ISO Diacetyl results in decreased expression of SORCS2 mRNA CTD PMID:30710127 NCBI chr14:79,538,911...79,912,333
Ensembl chr14:79,538,911...79,912,333
JBrowse link
G Spag17 sperm associated antigen 17 decreases expression ISO Diacetyl results in decreased expression of SPAG17 mRNA CTD PMID:30710127 NCBI chr 2:202,159,659...202,452,361
Ensembl chr 2:202,200,797...202,443,026
JBrowse link
G Tax1bp3 Tax1 binding protein 3 increases expression ISO Diacetyl results in increased expression of TAX1BP3 mRNA CTD PMID:30710127 NCBI chr10:59,743,356...59,748,063
Ensembl chr10:59,743,544...59,748,062
JBrowse link
G Tekt1 tektin 1 decreases expression ISO Diacetyl results in decreased expression of TEKT1 mRNA CTD PMID:30710127 NCBI chr10:58,895,689...58,924,098
Ensembl chr10:58,895,674...58,924,137
JBrowse link
G Tgfa transforming growth factor alpha increases secretion ISO Diacetyl results in increased secretion of TGFA protein CTD PMID:30851105 NCBI chr 4:117,961,877...118,045,923
Ensembl chr 4:117,962,319...118,046,344
JBrowse link
G Tnc tenascin C increases expression EXP Diacetyl results in increased expression of TNC protein CTD PMID:21464978 NCBI chr 5:79,789,686...79,874,555
Ensembl chr 5:79,789,671...79,874,671
JBrowse link
G Tnf tumor necrosis factor increases expression ISO Diacetyl results in increased expression of TNF mRNA CTD PMID:31381966 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link
G Tp63 tumor protein p63 affects expression ISO Diacetyl affects the expression of TP63 protein alternative form CTD PMID:32112875 NCBI chr11:78,234,853...78,456,559
Ensembl chr11:78,234,800...78,456,501
JBrowse link

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  CHEBI ontology 19810
    role 19758
      biological role 19758
        biochemical role 19304
          metabolite 19285
            prokaryotic metabolite 18400
              bacterial metabolite 18400
                Escherichia coli metabolite 18281
                  butane-2,3-dione 47
Path 2
Term Annotations click to browse term
  CHEBI ontology 19810
    subatomic particle 19808
      composite particle 19808
        hadron 19808
          baryon 19808
            nucleon 19808
              atomic nucleus 19808
                atom 19808
                  main group element atom 19696
                    p-block element atom 19696
                      carbon group element atom 19599
                        carbon atom 19588
                          organic molecular entity 19588
                            organic group 18527
                              organic divalent group 18520
                                organodiyl group 18520
                                  carbonyl group 18427
                                    carbonyl compound 18427
                                      ketone 16171
                                        diketone 1165
                                          alpha-diketone 191
                                            butane-2,3-dione 47
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