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
Accession: CHEBI:16583
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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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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
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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
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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
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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
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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
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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
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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
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Bcl2
BCL2, apoptosis regulator
decreases expression
ISO
Diacetyl results in decreased expression of BCL2 mRNA
CTD
PMID:37399938
NCBI chr13:22,689,783...22,853,920
Ensembl chr13:22,684,989...22,853,743 Ensembl chr13:22,684,989...22,853,743
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Casp3
caspase 3
increases expression
ISO
Diacetyl results in increased expression of CASP3 mRNA; Diacetyl results in increased expression of CASP3 protein
CTD
PMID:37399938
NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
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Cat
catalase
decreases expression
ISO
Diacetyl results in decreased expression of CAT protein
CTD
PMID:37399938
NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478
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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
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Ccnb1
cyclin B1
decreases expression
ISO
Diacetyl results in decreased expression of CCNB1 mRNA
CTD
PMID:37399938
NCBI chr 2:31,912,190...31,921,163
Ensembl chr 2:31,912,193...31,921,172
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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
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Cdk1
cyclin-dependent kinase 1
decreases expression
ISO
Diacetyl results in decreased expression of CDK1 mRNA
CTD
PMID:37399938
NCBI chr20:19,266,226...19,281,417
Ensembl chr20:19,266,248...19,281,408
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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
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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
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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
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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...106,008,293
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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
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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
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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
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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
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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
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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
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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
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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 chr14:91,176,979...91,349,722
Ensembl chr14:91,177,067...91,344,382
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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
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Gsr
glutathione-disulfide reductase
decreases expression
ISO
Diacetyl results in decreased expression of GSR protein
CTD
PMID:37399938
NCBI chr16:58,482,209...58,525,256
Ensembl chr16:58,482,505...58,525,661
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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
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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
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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
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Il10
interleukin 10
decreases expression
ISO
Diacetyl results in decreased expression of IL10 protein
CTD
PMID:37399938
NCBI chr13:42,472,625...42,477,308
Ensembl chr13:42,472,839...42,477,313
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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
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Il1b
interleukin 1 beta
increases expression
ISO
Diacetyl results in increased expression of IL1B protein
CTD
PMID:37399938
NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415
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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
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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
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Il6
interleukin 6
affects expression increases expression decreases expression
ISO EXP
Diacetyl analog affects the expression of IL6 mRNA Diacetyl results in increased expression of IL6 mRNA Diacetyl results in decreased expression of IL6 mRNA Diacetyl results in increased expression of IL6 protein
CTD
PMID:20200221 PMID:25145656 PMID:31381966 PMID:37399938
NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
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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
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Itgav
integrin subunit alpha V
decreases expression
ISO
Diacetyl results in decreased expression of ITGAV protein
CTD
PMID:34031698
NCBI chr 3:68,838,514...68,926,653
Ensembl chr 3:68,838,189...68,926,639
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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
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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
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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 7:132,846,132...132,851,861
Ensembl chr 7:132,846,136...132,851,850
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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
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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
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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
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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
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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...60,621,712
Ensembl chr 3:60,594,242...60,621,737
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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
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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
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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
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Pkp1
plakophilin 1
decreases expression
ISO
Diacetyl results in decreased expression of PKP1 protein
CTD
PMID:34031698
NCBI chr13:47,309,607...47,357,432
Ensembl chr13:47,309,614...47,357,465
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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
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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
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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
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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
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Ptgs2
prostaglandin-endoperoxide synthase 2
decreases expression
ISO
Diacetyl results in decreased expression of PTGS2 mRNA
CTD
PMID:30710127
NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188
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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
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Ripk3
receptor-interacting serine-threonine kinase 3
increases expression
ISO
Diacetyl results in increased expression of RIPK3 mRNA; Diacetyl results in increased expression of RIPK3 protein
CTD
PMID:37399938
NCBI chr15:29,283,153...29,292,107
Ensembl chr15:29,283,145...29,292,121
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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
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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
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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
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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
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Sqstm1
sequestosome 1
increases expression
ISO
Diacetyl results in increased expression of SQSTM1 protein
CTD
PMID:34031698
NCBI chr10:34,525,517...34,536,670
Ensembl chr10:34,525,519...34,536,673
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Tax1bp3
Tax1 binding protein 3
increases expression
ISO
Diacetyl results in increased expression of TAX1BP3 mRNA
CTD
PMID:30710127
NCBI chr10:57,795,845...57,800,363
Ensembl chr10:57,795,382...57,800,363
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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
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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
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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
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Tnf
tumor necrosis factor
increases expression
ISO
Diacetyl results in increased expression of TNF mRNA Diacetyl results in increased expression of TNF protein
CTD
PMID:31381966 PMID:37399938
NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
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Tp53
tumor protein p53
increases expression
ISO
Diacetyl results in increased expression of TRP53 mRNA
CTD
PMID:37399938
NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524
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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
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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
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Ubc
ubiquitin C
increases expression
EXP
Diacetyl results in increased expression of UBC protein
CTD
PMID:34031698
NCBI chr12:31,239,149...31,243,924
Ensembl chr12:31,239,152...31,243,925
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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
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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
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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
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