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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 B1 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 4:62,932,033...62,946,126
Ensembl chr 4:62,932,031...62,946,157
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 4:63,038,459...63,060,336
Ensembl chr 4:63,040,169...63,053,852
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 4:62,997,241...63,009,815
Ensembl chr 4:62,997,161...63,010,097
JBrowse link
G Alb albumin affects binding ISO
EXP
Diacetyl binds to ALB protein CTD PMID:25559854 NCBI chr14:17,607,397...17,622,814
Ensembl chr14:17,607,381...17,622,836
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 1:119,982,272...120,017,416
Ensembl chr 1:119,982,277...120,017,436
JBrowse link
G Aldh7a1 aldehyde dehydrogenase 7 family, member A1 decreases expression ISO Diacetyl results in decreased expression of ALDH7A1 protein CTD PMID:34031698 NCBI chr18:50,003,242...50,042,193
Ensembl chr18:50,009,934...50,042,193
JBrowse link
G Areg amphiregulin increases secretion ISO Diacetyl results in increased secretion of AREG protein CTD PMID:30851105 PMID:31381966 NCBI chr14:16,972,185...16,981,443
Ensembl chr14:16,972,187...16,981,535
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 1:205,817,374...205,823,928
Ensembl chr 1:205,817,378...205,837,807
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 chr14:67,349,004...67,435,883
Ensembl chr14:67,351,353...67,435,949
JBrowse link
G Cdc20b cell division cycle 20B decreases expression ISO Diacetyl results in decreased expression of CDC20B mRNA CTD PMID:30710127 NCBI chr 2:44,688,349...44,738,056 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 chr13:31,046,550...31,118,141
Ensembl chr13:31,046,535...31,116,899
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 chr15:3,852,381...3,918,036
Ensembl chr15:3,852,509...3,918,014
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 chr14:17,193,364...17,195,143
Ensembl chr14:17,193,365...17,195,215
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 chr10:106,006,404...106,008,294 JBrowse link
G Dhrs9 dehydrogenase/reductase 9 increases expression ISO Diacetyl results in increased expression of DHRS9 mRNA CTD PMID:30710127 NCBI chr 3:54,147,834...54,170,052
Ensembl chr 3:54,147,803...54,220,241
JBrowse link
G Dnaaf1 dynein, axonemal, assembly factor 1 decreases expression ISO Diacetyl results in decreased expression of DNAAF1 mRNA CTD PMID:30710127 NCBI chr19:47,624,534...47,652,314
Ensembl chr19:47,624,181...47,652,313
JBrowse link
G Dnah12 dynein, axonemal, heavy chain 12 decreases expression ISO Diacetyl results in decreased expression of DNAH12 mRNA CTD PMID:30710127 NCBI chr16:1,936,354...2,092,663
Ensembl chr16:1,937,817...2,092,664
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 1:174,305,929...174,479,490
Ensembl chr 1:174,306,644...174,479,474
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 4:105,064,123...105,284,361
Ensembl chr 4:105,064,125...105,284,376
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 5:56,730,179...56,800,926
Ensembl chr 5:56,730,179...56,800,925
JBrowse link
G Dsp desmoplakin decreases expression ISO Diacetyl results in decreased expression of DSP protein CTD PMID:34031698 NCBI chr17:26,623,602...26,671,692
Ensembl chr17:26,623,588...26,671,800
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 chr14:91,176,931...91,349,722
Ensembl chr14:91,177,067...91,344,382
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 8:78,629,899...78,668,547
Ensembl chr 8:78,630,127...78,668,544
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 9:23,703,476...23,720,121
Ensembl chr 9:23,703,477...23,720,121
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 chr18:28,106,284...28,116,167
Ensembl chr18:28,105,760...28,116,441
JBrowse link
G Hmox1 heme oxygenase 1 increases expression EXP Diacetyl results in increased expression of HMOX1 mRNA CTD PMID:25145656 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
JBrowse link
G Il13 interleukin 13 increases expression ISO Diacetyl results in increased expression of IL13 protein CTD PMID:29233007 NCBI chr10:37,790,130...37,792,687
Ensembl chr10:37,790,130...37,792,737
JBrowse link
G Il2 interleukin 2 increases expression ISO Diacetyl results in increased expression of IL2 protein CTD PMID:29233007 NCBI chr 2:120,004,862...120,009,566
Ensembl chr 2:120,004,862...120,009,566
JBrowse link
G Il4 interleukin 4 increases expression ISO Diacetyl results in increased expression of IL4 protein CTD PMID:29233007 NCBI chr10:37,771,203...37,776,750
Ensembl chr10:37,771,203...37,776,750
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 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Itga6 integrin subunit alpha 6 decreases expression ISO Diacetyl results in decreased expression of ITGA6 protein CTD PMID:34031698 NCBI chr 3:56,604,512...56,689,428
Ensembl chr 3:56,617,268...56,689,428
JBrowse link
G Itgav integrin subunit alpha V decreases expression ISO Diacetyl results in decreased expression of ITGAV protein CTD PMID:34031698 NCBI chr 3:68,838,524...68,926,653
Ensembl chr 3:68,838,189...68,926,639
JBrowse link
G Itgb4 integrin subunit beta 4 decreases expression ISO Diacetyl results in decreased expression of ITGB4 protein CTD PMID:34031698 NCBI chr10:101,206,657...101,243,012
Ensembl chr10:101,206,665...101,243,012
JBrowse link
G Krt19 keratin 19 decreases expression ISO Diacetyl results in decreased expression of KRT19 protein CTD PMID:34031698 NCBI chr10:85,075,835...85,080,552
Ensembl chr10:85,066,802...85,171,799
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 7:132,846,355...132,851,986
Ensembl chr 7:132,846,136...132,851,850
JBrowse link
G Macrod2 mono-ADP ribosylhydrolase 2 decreases expression ISO Diacetyl results in decreased expression of MACROD2 mRNA CTD PMID:30710127 NCBI chr 3:127,720,066...129,737,511
Ensembl chr 3:127,720,181...129,734,492
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 chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616
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 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
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 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120
JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 affects localization EXP Diacetyl affects the localization of NFE2L2 protein CTD PMID:25145656 NCBI chr 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737
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 2:224,016,214...224,132,135
Ensembl chr 2:224,016,214...224,110,404
JBrowse link
G Nnt nicotinamide nucleotide transhydrogenase decreases expression ISO Diacetyl results in decreased expression of NNT protein CTD PMID:34031698 NCBI chr 2:51,411,413...51,505,125
Ensembl chr 2:51,411,413...51,504,823
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 1:230,454,314...230,539,332
Ensembl chr 1:230,454,426...230,539,331
JBrowse link
G Pkp1 plakophilin 1 decreases expression ISO Diacetyl results in decreased expression of PKP1 protein CTD PMID:34031698 NCBI chr13:47,309,603...47,357,551
Ensembl chr13:47,309,614...47,357,465
JBrowse link
G Prom1 prominin 1 decreases expression ISO Diacetyl results in decreased expression of PROM1 mRNA CTD PMID:30710127 NCBI chr14:66,989,545...67,094,534
Ensembl chr14:66,990,160...67,094,527
JBrowse link
G Psmb5 proteasome 20S subunit beta 5 increases expression ISO Diacetyl results in increased expression of PSMB5 protein CTD PMID:34031698 NCBI chr15:28,072,772...28,077,367
Ensembl chr15:28,072,781...28,077,440
JBrowse link
G Psmc1 proteasome 26S subunit, ATPase 1 increases expression ISO Diacetyl results in increased expression of PSMC1 protein CTD PMID:34031698 NCBI chr 6:119,392,833...119,405,233
Ensembl chr 6:119,392,855...119,410,123
JBrowse link
G Ptges2 prostaglandin E synthase 2 increases expression ISO Diacetyl results in increased expression of PTGES2 mRNA CTD PMID:31381966 NCBI chr 3:15,690,501...15,697,688
Ensembl chr 3:15,690,501...15,697,688
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 decreases expression ISO Diacetyl results in decreased expression of PTGS2 mRNA CTD PMID:30710127 NCBI chr13:62,164,080...62,169,770
Ensembl chr13:62,163,932...62,172,188
JBrowse link
G Pthlh parathyroid hormone-like hormone decreases expression ISO Diacetyl results in decreased expression of PTHLH mRNA CTD PMID:30710127 NCBI chr 4:180,188,792...180,199,847
Ensembl chr 4:180,188,792...180,199,847
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 1:205,977,060...205,980,610
Ensembl chr 1:205,977,060...205,980,610
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 3:153,082,208...153,084,457
Ensembl chr 3:153,082,369...153,084,453
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 chr14:74,371,089...74,735,943
Ensembl chr14:74,371,415...74,735,943
JBrowse link
G Spag17 sperm associated antigen 17 decreases expression ISO Diacetyl results in decreased expression of SPAG17 mRNA CTD PMID:30710127 NCBI chr 2:187,264,004...187,511,061
Ensembl chr 2:187,264,009...187,510,501
JBrowse link
G Sqstm1 sequestosome 1 increases expression ISO Diacetyl results in increased expression of SQSTM1 protein CTD PMID:34031698 NCBI chr10:34,525,517...34,536,685
Ensembl chr10:34,525,519...34,536,673
JBrowse link
G Tax1bp3 Tax1 binding protein 3 increases expression ISO Diacetyl results in increased expression of TAX1BP3 mRNA CTD PMID:30710127 NCBI chr10:57,795,785...57,800,363
Ensembl chr10:57,795,382...57,800,363
JBrowse link
G Tekt1 tektin 1 decreases expression ISO Diacetyl results in decreased expression of TEKT1 mRNA CTD PMID:30710127 NCBI chr10:56,952,164...56,980,572
Ensembl chr10:56,952,167...56,980,572
JBrowse link
G Tgfa transforming growth factor alpha increases secretion ISO Diacetyl results in increased secretion of TGFA protein CTD PMID:30851105 NCBI chr 4:118,618,043...118,700,897
Ensembl chr 4:118,618,269...118,700,894
JBrowse link
G Tnc tenascin C increases expression EXP Diacetyl results in increased expression of TNC protein CTD PMID:21464978 NCBI chr 5:77,375,851...77,460,712
Ensembl chr 5:77,375,851...77,460,624
JBrowse link
G Tnf tumor necrosis factor increases expression ISO Diacetyl results in increased expression of TNF mRNA CTD PMID:31381966 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Tp63 tumor protein p63 affects expression ISO Diacetyl affects the expression of TP63 protein alternative form CTD PMID:32112875 NCBI chr11:74,838,858...75,049,764
Ensembl chr11:74,838,859...75,049,398
JBrowse link
G Trip12 thyroid hormone receptor interactor 12 increases expression ISO Diacetyl results in increased expression of TRIP12 protein CTD PMID:34031698 NCBI chr 9:85,916,691...86,043,312
Ensembl chr 9:85,916,691...86,051,403
JBrowse link
G Ubc ubiquitin C increases expression EXP Diacetyl results in increased expression of UBC protein CTD PMID:34031698 NCBI chr12:31,238,889...31,243,924
Ensembl chr12:31,239,152...31,243,925
JBrowse link
G Ube2l3 ubiquitin-conjugating enzyme E2L 3 increases expression ISO Diacetyl results in increased expression of UBE2L3 protein CTD PMID:34031698 NCBI chr11:83,797,722...83,838,862
Ensembl chr11:83,797,722...83,838,862
JBrowse link
G Uchl5 ubiquitin C-terminal hydrolase L5 increases expression ISO Diacetyl results in increased expression of UCHL5 protein CTD PMID:34031698 NCBI chr13:55,520,722...55,556,503
Ensembl chr13:55,520,729...55,556,502
JBrowse link
G Usp14 ubiquitin specific peptidase 14 increases expression ISO Diacetyl results in increased expression of USP14 protein CTD PMID:34031698 NCBI chr18:1,018,111...1,057,727
Ensembl chr18:1,019,400...1,057,519
JBrowse link

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Term Annotations click to browse term
  CHEBI ontology 20089
    role 20042
      biological role 20011
        biochemical role 19671
          metabolite 19631
            prokaryotic metabolite 18629
              bacterial metabolite 18654
                Escherichia coli metabolite 18549
                  butane-2,3-dione 66
Path 2
Term Annotations click to browse term
  CHEBI ontology 20089
    subatomic particle 20058
      composite particle 20058
        hadron 20088
          baryon 20088
            nucleon 20088
              atomic nucleus 20088
                atom 20058
                  main group element atom 19960
                    p-block element atom 19990
                      carbon group element atom 19916
                        carbon atom 19909
                          organic molecular entity 19909
                            organic group 18988
                              organic divalent group 18950
                                organodiyl group 18974
                                  carbonyl group 18903
                                    carbonyl compound 18925
                                      ketone 17115
                                        diketone 1225
                                          alpha-diketone 209
                                            butane-2,3-dione 66
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