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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:acrylonitrile
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Accession:CHEBI:28217 term browser browse the term
Definition:A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an ethenyl group.
Synonyms:related_synonym: 2-propenenitrile;   Acrylnitril;   Acrylsaeurenitril;   Formula=C3H3N;   InChI=1S/C3H3N/c1-2-3-4/h2H,1H2;   InChIKey=NLHHRLWOUZZQLW-UHFFFAOYSA-N;   Propenenitrile;   SMILES=C=CC#N;   Vinyl cyanide;   cyanure de vinyle;   nitrile acrylique
 alt_id: CHEBI:22217;   CHEBI:2442
 xref: CAS:107-13-1;   KEGG:C01998
 xref_mesh: MESH:D000181
 xref: PDBeChem:6AC;   PMID:12075111;   PMID:23043843;   PMID:24248151;   PMID:28782019;   PMID:28965700;   PMID:29217572;   PMID:29713581;   PMID:8330351;   PMID:9598299;   PPDB:2545;   Reaxys:605310;   UM-BBD_compID:c0148


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acrylonitrile term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Alpl alkaline phosphatase, biomineralization associated multiple interactions ISO [[Volatile Organic Compounds results in increased abundance of Acrylonitrile] which results in increased abundance of N-acetyl-S-(2-cyanoethyl)cysteine] which results in increased expression of ALPL protein CTD PMID:34668566 NCBI chr 5:149,951,397...150,006,424
Ensembl chr 5:149,951,409...150,006,446 		JBrowse link
G Apex2 apurinic/apyrimidinic endodeoxyribonuclease 2 increases expression
multiple interactions		 EXP Acrylonitrile results in increased expression of APEX2 mRNA
Acetylcysteine inhibits the reaction [Acrylonitrile results in increased expression of APEX2 mRNA]; alpha-Tocopherol inhibits the reaction [Acrylonitrile results in increased expression of APEX2 mRNA]; Plant Extracts inhibits the reaction [Acrylonitrile results in increased expression of APEX2 mRNA]		 CTD PMID:26332274 NCBI chr  X:19,425,684...19,508,459
Ensembl chr  X:19,487,419...19,508,439 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator increases expression
multiple interactions		 ISO Acrylonitrile results in increased expression of BAX protein
Acetylcysteine inhibits the reaction [Acrylonitrile results in increased expression of BAX protein]
Acrylonitrile results in increased expression of BAX mRNA; Acrylonitrile results in increased expression of BAX protein		 CTD PMID:16173056 PMID:20981856 PMID:33132245 PMID:35429547 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368 		JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression ISO Acrylonitrile results in decreased expression of BCL2 protein
Acrylonitrile results in decreased expression of BCL2 mRNA; Acrylonitrile results in decreased expression of BCL2 protein		 CTD PMID:16173056 PMID:35429547 NCBI chr13:22,689,783...22,853,920
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		JBrowse link
G Bcl2l1 Bcl2-like 1 decreases expression ISO Acrylonitrile results in decreased expression of BCL2L1 protein CTD PMID:33132245 NCBI chr 3:141,253,508...141,304,582
Ensembl chr 3:141,253,523...141,303,479 		JBrowse link
G Becn1 beclin 1 increases expression ISO Acrylonitrile results in increased expression of BECN1 mRNA CTD PMID:35429547 NCBI chr10:86,231,387...86,246,742
Ensembl chr10:86,231,388...86,246,742 		JBrowse link
G Casp12 caspase 12 increases expression ISO Acrylonitrile results in increased expression of CASP12 protein CTD PMID:33132245 NCBI chr 8:2,642,296...2,669,549
Ensembl chr 8:2,642,434...2,674,037 		JBrowse link
G Casp3 caspase 3 increases activity
multiple interactions
increases cleavage
increases expression		 ISO Acrylonitrile results in increased activity of CASP3 protein
Acetylcysteine inhibits the reaction [Acrylonitrile results in increased activity of CASP3 protein]
Acrylonitrile results in increased cleavage of CASP3 protein
Acrylonitrile results in increased expression of CASP3 mRNA		 CTD PMID:20981856 PMID:35429547 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Cat catalase decreases activity
multiple interactions
increases expression		 EXP
ISO		 Acrylonitrile results in decreased activity of CAT protein
Curcumin inhibits the reaction [Acrylonitrile results in decreased activity of CAT protein]
Acrylonitrile results in increased expression of CAT protein		 CTD PMID:19913070 PMID:20127315 PMID:35429547 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478 		JBrowse link
G Cbs cystathionine beta synthase decreases expression EXP Acrylonitrile results in decreased expression of CBS protein CTD PMID:33486070 NCBI chr20:9,708,089...9,732,623
Ensembl chr20:9,708,090...9,732,764 		JBrowse link
G Ccl2 C-C motif chemokine ligand 2 decreases expression
multiple interactions
increases expression		 ISO
EXP		 Acrylonitrile results in decreased expression of CCL2 mRNA
Acetylcysteine inhibits the reaction [Acrylonitrile results in increased expression of CCL2 mRNA]; alpha-Tocopherol inhibits the reaction [Acrylonitrile results in increased expression of CCL2 mRNA]; Plant Extracts inhibits the reaction [Acrylonitrile results in increased expression of CCL2 mRNA]		 CTD PMID:16173056 PMID:26332274 NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226 		JBrowse link
G Ccnd1 cyclin D1 multiple interactions
increases expression
decreases expression		 EXP
ISO		 Acetylcysteine inhibits the reaction [Acrylonitrile results in increased expression of CCND1 mRNA]; alpha-Tocopherol inhibits the reaction [Acrylonitrile results in increased expression of CCND1 mRNA]; Plant Extracts inhibits the reaction [Acrylonitrile results in increased expression of CCND1 mRNA]
Acrylonitrile results in increased expression of CCND1 protein
Acrylonitrile results in decreased expression of CCND1 protein		 CTD PMID:26332274 PMID:30236600 PMID:33132245 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602 		JBrowse link
G Ccnd2 cyclin D2 multiple interactions
increases expression		 EXP Acetylcysteine inhibits the reaction [Acrylonitrile results in increased expression of CCND2 mRNA]; alpha-Tocopherol inhibits the reaction [Acrylonitrile results in increased expression of CCND2 mRNA]; Plant Extracts inhibits the reaction [Acrylonitrile results in increased expression of CCND2 mRNA] CTD PMID:26332274 NCBI chr 4:159,966,883...159,989,261
Ensembl chr 4:159,962,363...159,989,495 		JBrowse link
G Ccne1 cyclin E1 increases expression
decreases expression		 ISO Acrylonitrile results in increased expression of CCNE1 protein
Acrylonitrile results in decreased expression of CCNE1 protein		 CTD PMID:30236600 PMID:33132245 NCBI chr 1:90,781,947...90,791,188
Ensembl chr 1:90,781,949...90,791,101 		JBrowse link
G Cdh1 cadherin 1 decreases expression ISO Acrylonitrile results in decreased expression of CDH1 protein CTD PMID:30236600 NCBI chr19:34,492,371...34,561,775
Ensembl chr19:34,492,371...34,561,775 		JBrowse link
G Cdh2 cadherin 2 increases expression ISO Acrylonitrile results in increased expression of CDH2 protein CTD PMID:30236600 NCBI chr18:7,776,704...7,990,934
Ensembl chr18:7,776,704...7,990,167 		JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A multiple interactions
increases expression
decreases expression		 EXP
ISO		 Acetylcysteine inhibits the reaction [Acrylonitrile results in increased expression of CDKN1A mRNA]; alpha-Tocopherol inhibits the reaction [Acrylonitrile results in increased expression of CDKN1A mRNA]; Plant Extracts inhibits the reaction [Acrylonitrile results in increased expression of CDKN1A mRNA]
Acrylonitrile results in decreased expression of CDKN1A protein
Acrylonitrile results in increased expression of CDKN1A protein		 CTD PMID:10451498 PMID:26332274 PMID:30236600 PMID:33132245 NCBI chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585 		JBrowse link
G Cdkn1b cyclin-dependent kinase inhibitor 1B decreases expression
increases expression		 ISO Acrylonitrile results in decreased expression of CDKN1B protein
Acrylonitrile results in increased expression of CDKN1B protein		 CTD PMID:30236600 PMID:33132245 NCBI chr 4:167,760,067...167,765,177
Ensembl chr 4:167,760,181...167,764,982 		JBrowse link
G Cth cystathionine gamma-lyase decreases expression EXP Acrylonitrile results in decreased expression of CTH protein CTD PMID:33486070 NCBI chr 2:246,975,888...247,002,234
Ensembl chr 2:246,975,894...247,002,234 		JBrowse link
G Cxcr4 C-X-C motif chemokine receptor 4 decreases expression ISO Acrylonitrile results in decreased expression of CXCR4 mRNA CTD PMID:16173056 NCBI chr13:40,077,976...40,081,883
Ensembl chr13:40,077,976...40,081,883 		JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 affects response to substance
increases oxidation
multiple interactions
increases expression
increases metabolic processing		 EXP
ISO		 CYP2E1 protein affects the susceptibility to Acrylonitrile
CYP2E1 protein results in increased oxidation of Acrylonitrile
Acetylcysteine promotes the reaction [Acrylonitrile results in increased expression of CYP2E1 mRNA]; Acrylonitrile inhibits the reaction [[Benzene results in increased expression of CYP2E1 protein] which results in increased metabolism of Benzene]; alpha-Tocopherol promotes the reaction [Acrylonitrile results in increased expression of CYP2E1 mRNA]; Plant Extracts promotes the reaction [Acrylonitrile results in increased expression of CYP2E1 mRNA]
[CYP2E1 protein results in increased metabolism of Acrylonitrile] which results in increased chemical synthesis of 2-cyanoethylene oxide; CYP2E1 gene mutant form inhibits the reaction [Acrylonitrile results in increased mutagenesis of HPRT1 gene]		 CTD PMID:1664256 PMID:9010585 PMID:20127315 PMID:26332274 PMID:32529832 NCBI chr 1:195,840,330...195,850,728
Ensembl chr 1:195,840,058...195,864,023 		JBrowse link
G Ddit3 DNA-damage inducible transcript 3 increases expression ISO Acrylonitrile results in increased expression of DDIT3 protein
Acrylonitrile results in increased expression of DDIT3 mRNA		 CTD PMID:33132245 PMID:35429547 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201 		JBrowse link
G Eif2s1 eukaryotic translation initiation factor 2 subunit alpha increases expression ISO Acrylonitrile results in increased expression of EIF2S1 protein modified form CTD PMID:33132245 NCBI chr 6:97,672,829...97,697,499
Ensembl chr 6:97,672,766...97,706,225 		JBrowse link
G Fos Fos proto-oncogene, AP-1 transcription factor subunit decreases expression ISO Acrylonitrile results in decreased expression of FOS protein CTD PMID:16173056 NCBI chr 6:105,121,170...105,124,036
Ensembl chr 6:105,121,170...105,124,036 		JBrowse link
G Gpx3 glutathione peroxidase 3 increases expression ISO Acrylonitrile results in increased expression of GPX3 protein CTD PMID:35429547 NCBI chr10:39,028,624...39,036,695
Ensembl chr10:39,028,570...39,037,035 		JBrowse link
G H2ax H2A.X variant histone increases expression ISO Acrylonitrile results in increased expression of H2AX protein CTD PMID:35429547 NCBI chr 8:44,671,907...44,673,262
Ensembl chr 8:44,671,786...44,673,239 		JBrowse link
G Hmox1 heme oxygenase 1 increases expression ISO Acrylonitrile results in increased expression of HMOX1 protein CTD PMID:14644359 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079 		JBrowse link
G Hprt1 hypoxanthine phosphoribosyltransferase 1 increases mutagenesis
multiple interactions		 EXP
ISO		 Acrylonitrile results in increased mutagenesis of HPRT1 gene
CYP2E1 gene mutant form inhibits the reaction [Acrylonitrile results in increased mutagenesis of HPRT1 gene]		 CTD PMID:32529823 PMID:32529832 NCBI chr  X:132,736,175...132,768,149
Ensembl chr  X:132,736,096...132,768,154 		JBrowse link
G Hspa5 heat shock protein family A (Hsp70) member 5 increases expression ISO Acrylonitrile results in increased expression of HSPA5 mRNA CTD PMID:35429547 NCBI chr 3:18,055,507...18,059,969
Ensembl chr 3:18,055,405...18,059,891 		JBrowse link
G Il1b interleukin 1 beta multiple interactions
increases expression		 EXP Acetylcysteine inhibits the reaction [Acrylonitrile results in increased expression of IL1B mRNA]; alpha-Tocopherol inhibits the reaction [Acrylonitrile results in increased expression of IL1B mRNA]; Plant Extracts inhibits the reaction [Acrylonitrile results in increased expression of IL1B mRNA] CTD PMID:26332274 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Il6 interleukin 6 increases expression ISO Acrylonitrile results in increased expression of IL6 protein CTD PMID:35429547 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Jun Jun proto-oncogene, AP-1 transcription factor subunit decreases expression ISO Acrylonitrile results in decreased expression of JUN protein CTD PMID:16173056 NCBI chr 5:109,894,175...109,897,268
Ensembl chr 5:109,893,145...109,897,656 		JBrowse link
G Map1lc3a microtubule-associated protein 1 light chain 3 alpha increases expression ISO Acrylonitrile results in increased expression of MAP1LC3A mRNA CTD PMID:35429547 NCBI chr 3:143,783,024...143,784,670
Ensembl chr 3:143,783,024...143,784,670 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation
multiple interactions		 ISO Acrylonitrile results in increased phosphorylation of MAPK1 protein
2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [Acrylonitrile results in increased phosphorylation of MAPK1 protein]; bisindolylmaleimide I inhibits the reaction [Acrylonitrile results in increased phosphorylation of MAPK1 protein]; rottlerin inhibits the reaction [Acrylonitrile results in increased phosphorylation of MAPK1 protein]; Tetradecanoylphorbol Acetate inhibits the reaction [Acrylonitrile results in increased phosphorylation of MAPK1 protein]; U 0126 inhibits the reaction [Acrylonitrile results in increased phosphorylation of MAPK1 protein]		 CTD PMID:17080406 PMID:30236600 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 multiple interactions
increases phosphorylation		 ISO 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [Acrylonitrile results in increased phosphorylation of MAPK3 protein]; bisindolylmaleimide I inhibits the reaction [Acrylonitrile results in increased phosphorylation of MAPK3 protein]; rottlerin inhibits the reaction [Acrylonitrile results in increased phosphorylation of MAPK3 protein]; Tetradecanoylphorbol Acetate inhibits the reaction [Acrylonitrile results in increased phosphorylation of MAPK3 protein]; U 0126 inhibits the reaction [Acrylonitrile results in increased phosphorylation of MAPK3 protein] CTD PMID:17080406 PMID:30236600 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mapk8 mitogen-activated protein kinase 8 increases expression ISO Acrylonitrile results in increased expression of MAPK8 mRNA CTD PMID:35429547 NCBI chr16:8,638,897...8,721,960
Ensembl chr16:8,638,924...8,721,981 		JBrowse link
G Mpst mercaptopyruvate sulfurtransferase decreases expression EXP Acrylonitrile results in decreased expression of MPST protein CTD PMID:33486070 NCBI chr 7:109,955,581...109,963,155
Ensembl chr 7:109,955,675...109,963,141 		JBrowse link
G Mtor mechanistic target of rapamycin kinase increases expression ISO Acrylonitrile results in increased expression of MTOR mRNA CTD PMID:35429547 NCBI chr 5:158,884,856...158,994,311
Ensembl chr 5:158,884,804...158,994,311 		JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 increases activity
increases expression		 ISO Acrylonitrile results in increased activity of NQO1 protein
Acrylonitrile results in increased expression of NQO1 mRNA		 CTD PMID:9029048 NCBI chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557 		JBrowse link
G Ocln occludin decreases expression ISO Acrylonitrile results in decreased expression of OCLN protein CTD PMID:30236600 NCBI chr 2:31,657,217...31,707,466
Ensembl chr 2:31,657,220...31,764,150 		JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage
multiple interactions		 ISO Acrylonitrile results in increased cleavage of PARP1 protein
Acetylcysteine inhibits the reaction [Acrylonitrile results in increased cleavage of PARP1 protein]		 CTD PMID:20981856 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404 		JBrowse link
G Plcb1 phospholipase C beta 1 affects localization EXP Acrylonitrile affects the localization of PLCB1 protein CTD PMID:12850505 NCBI chr 3:122,059,988...122,772,896
Ensembl chr 3:122,060,031...122,772,869 		JBrowse link
G Plcd1 phospholipase C, delta 1 multiple interactions EXP Acrylonitrile results in increased expression of and affects the localization of PLCD1 protein CTD PMID:12850505 NCBI chr 8:118,795,196...118,818,186
Ensembl chr 8:118,795,201...118,818,186 		JBrowse link
G Plcg1 phospholipase C, gamma 1 increases expression EXP Acrylonitrile results in increased expression of PLCG1 protein CTD PMID:12850505 NCBI chr 3:149,385,587...149,416,330
Ensembl chr 3:149,385,587...149,416,330 		JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit increases expression ISO Acrylonitrile results in increased expression of RELA protein CTD PMID:35429547 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G S100a8 S100 calcium binding protein A8 decreases expression ISO Acrylonitrile results in decreased expression of S100A8 mRNA CTD PMID:16173056 NCBI chr 2:176,166,517...176,167,645
Ensembl chr 2:176,167,124...176,167,643 		JBrowse link
G Snai2 snail family transcriptional repressor 2 increases expression ISO Acrylonitrile results in increased expression of SNAI2 protein CTD PMID:30236600 NCBI chr11:86,182,788...86,186,203
Ensembl chr11:86,181,909...86,186,200 		JBrowse link
G Sod1 superoxide dismutase 1 increases expression ISO Acrylonitrile results in increased expression of SOD1 protein CTD PMID:35429547 NCBI chr11:29,456,673...29,462,249
Ensembl chr11:29,456,558...29,462,249 		JBrowse link
G Sod2 superoxide dismutase 2 increases expression ISO Acrylonitrile results in increased expression of SOD2 protein CTD PMID:35429547 NCBI chr 1:47,638,318...47,645,163
Ensembl chr 1:47,636,528...47,645,189 		JBrowse link
G Th tyrosine hydroxylase multiple interactions EXP Acrylonitrile inhibits the reaction [3,3'-iminodipropionitrile results in increased expression of TH protein] CTD PMID:19244277 NCBI chr 1:198,071,500...198,078,832
Ensembl chr 1:198,071,503...198,109,767 		JBrowse link
G Tnf tumor necrosis factor multiple interactions
increases expression		 EXP
ISO		 Acetylcysteine inhibits the reaction [Acrylonitrile results in increased expression of TNF mRNA]; alpha-Tocopherol inhibits the reaction [Acrylonitrile results in increased expression of TNF mRNA]; Plant Extracts inhibits the reaction [Acrylonitrile results in increased expression of TNF mRNA]
Acrylonitrile results in increased expression of TNF protein		 CTD PMID:26332274 PMID:35429547 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Tp53 tumor protein p53 increases expression ISO Acrylonitrile results in increased expression of TP53 protein CTD PMID:33132245 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
G Xrcc6 X-ray repair cross complementing 6 multiple interactions
increases expression		 EXP Acetylcysteine promotes the reaction [Acrylonitrile results in increased expression of XRCC6 mRNA]; alpha-Tocopherol promotes the reaction [Acrylonitrile results in increased expression of XRCC6 mRNA]; Plant Extracts promotes the reaction [Acrylonitrile results in increased expression of XRCC6 mRNA] CTD PMID:26332274 NCBI chr 7:113,542,992...113,563,762
Ensembl chr 7:113,543,057...113,563,762 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19890
    role 19839
      biological role 19858
        antimicrobial agent 18239
          antifungal agent 17176
            acrylonitrile 53
              allylidyne group 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19890
    subatomic particle 19867
      composite particle 19888
        hadron 19888
          baryon 19888
            nucleon 19867
              atomic nucleus 19888
                atom 19888
                  main group element atom 19806
                    p-block element atom 19806
                      carbon group element atom 19746
                        carbon atom 19743
                          organic molecular entity 19743
                            one-carbon compound 17886
                              hydrogen cyanide 4795
                                cyanides 4778
                                  nitrile 4575
                                    aliphatic nitrile 2206
                                      acrylonitrile 53
                                        allylidyne group 0
paths to the root