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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Definition:A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an ethenyl group.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: Beilstein:605310;   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 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:23,146,085...23,166,676
Ensembl chr  X:23,146,085...23,166,675
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]
CTD PMID:16173056, PMID:20981856 NCBI chr 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression ISO Acrylonitrile results in decreased expression of BCL2 protein CTD PMID:16173056 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
JBrowse link
G Casp3 caspase 3 increases activity
multiple interactions
ISO Acrylonitrile results in increased activity of CASP3 protein
Acetylcysteine inhibits the reaction [Acrylonitrile results in increased activity of CASP3 protein]
CTD PMID:20981856 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Cat catalase decreases activity
multiple interactions
EXP Acrylonitrile results in decreased activity of CAT protein
Curcumin inhibits the reaction [Acrylonitrile results in decreased activity of CAT protein]
CTD PMID:19913070, PMID:20127315 NCBI chr 3:93,379,872...93,412,058
Ensembl chr 3:93,379,874...93,412,058
JBrowse link
G Ccl2 C-C motif chemokine ligand 2 decreases expression
increases expression
multiple interactions
ISO
EXP
Acrylonitrile results in decreased expression of CCL2 mRNA
Acrylonitrile results in increased 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 chr10:69,412,065...69,413,863
Ensembl chr10:69,412,017...69,413,870
JBrowse link
G Ccnd1 cyclin D1 multiple interactions
increases 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
CTD PMID:26332274, PMID:30236600 NCBI chr 1:218,090,750...218,100,447
Ensembl chr 1:218,090,750...218,100,325
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 4:159,674,885...159,697,207
Ensembl chr 4:159,674,885...159,697,207
JBrowse link
G Ccne1 cyclin E1 increases expression ISO Acrylonitrile results in increased expression of CCNE1 protein CTD PMID:30236600 NCBI chr 1:94,485,830...94,495,112
Ensembl chr 1:94,485,832...94,494,980
JBrowse link
G Cdh1 cadherin 1 decreases expression ISO Acrylonitrile results in decreased expression of CDH1 protein CTD PMID:30236600 NCBI chr19:38,768,467...38,838,395
Ensembl chr19:38,768,467...38,838,395
JBrowse link
G Cdh2 cadherin 2 increases expression ISO Acrylonitrile results in increased expression of CDH2 protein CTD PMID:30236600 NCBI chr18:8,146,971...8,366,037
Ensembl chr18:8,146,971...8,360,684
JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A multiple interactions
decreases expression
increases 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
CTD PMID:10451498, PMID:26332274, PMID:30236600 NCBI chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
JBrowse link
G Cdkn1b cyclin-dependent kinase inhibitor 1B decreases expression ISO Acrylonitrile results in decreased expression of CDKN1B protein CTD PMID:30236600 NCBI chr 4:168,689,043...168,694,159
Ensembl chr 4:168,689,163...168,693,964
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 chr13:45,314,952...45,318,856
Ensembl chr13:45,314,933...45,318,878
JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 affects response to substance
increases metabolic processing
multiple interactions
increases expression
increases oxidation
EXP
ISO
CYP2E1 protein affects the susceptibility to Acrylonitrile
CYP2E1 protein results in increased metabolism of Acrylonitrile
[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 HPRT gene]
Acrylonitrile results in increased expression of CYP2E1 mRNA
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 oxidation of Acrylonitrile
CTD PMID:1664256, PMID:9010585, PMID:20127315, PMID:26332274, PMID:32529832 NCBI chr 1:213,511,892...213,522,195
Ensembl chr 1:213,511,874...213,535,542
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 6:109,300,433...109,303,299
Ensembl chr 6:109,300,433...109,303,299
JBrowse link
G Hmox1 heme oxygenase 1 increases expression ISO Acrylonitrile results in increased expression of HMOX1 protein CTD PMID:14644359 NCBI chr19:14,508,634...14,515,455
Ensembl chr19:14,508,616...14,515,456
JBrowse link
G Hprt1 hypoxanthine phosphoribosyltransferase 1 multiple interactions
increases mutagenesis
ISO
EXP
CYP2E1 gene mutant form inhibits the reaction [Acrylonitrile results in increased mutagenesis of HPRT gene] CTD PMID:32529823, PMID:32529832 NCBI chr  X:158,196,640...158,228,815
Ensembl chr  X:158,197,149...158,228,749
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 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
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 5:114,011,184...114,014,277
Ensembl chr 5:114,011,189...114,014,277
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 chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
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 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
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 chr19:38,422,210...38,437,103
Ensembl chr19:38,422,164...38,437,180
JBrowse link
G Ocln occludin decreases expression ISO Acrylonitrile results in decreased expression of OCLN protein CTD PMID:30236600 NCBI chr 2:30,527,327...30,577,218
Ensembl chr 2:30,527,715...30,577,218
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 chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
JBrowse link
G Plcb1 phospholipase C beta 1 affects localization EXP Acrylonitrile affects the localization of PLCB1 protein CTD PMID:12850505 NCBI chr 3:127,721,244...128,419,565
Ensembl chr 3:128,155,069...128,419,545
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 8:127,753,514...127,782,070
Ensembl chr 8:127,753,539...127,782,070
JBrowse link
G Plcg1 phospholipase C, gamma 1 increases expression EXP Acrylonitrile results in increased expression of PLCG1 protein CTD PMID:12850505 NCBI chr 3:156,727,642...156,758,307
Ensembl chr 3:156,727,642...156,758,307
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 2:190,073,239...190,074,333
Ensembl chr 2:190,073,815...190,074,354
JBrowse link
G Snai2 snail family transcriptional repressor 2 increases expression ISO Acrylonitrile results in increased expression of SNAI2 protein CTD PMID:30236600 NCBI chr11:90,404,421...90,406,730
Ensembl chr11:90,403,333...90,406,797
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 1:216,073,034...216,080,287
Ensembl chr 1:216,073,031...216,080,287
JBrowse link
G Tnf tumor necrosis factor multiple interactions
increases expression
EXP 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] CTD PMID:26332274 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
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 7:123,259,881...123,280,613
Ensembl chr 7:123,259,761...123,280,612
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19785
    role 19732
      biological role 19732
        aetiopathogenetic role 18936
          carcinogenic agent 18312
            acrylonitrile 33
              allylidyne group 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19785
    subatomic particle 19782
      composite particle 19782
        hadron 19782
          baryon 19782
            nucleon 19782
              atomic nucleus 19782
                atom 19782
                  main group element atom 19670
                    p-block element atom 19670
                      carbon group element atom 19572
                        carbon atom 19561
                          organic molecular entity 19561
                            one-carbon compound 17539
                              hydrogen cyanide 2886
                                cyanides 2886
                                  nitrile 2881
                                    aliphatic nitrile 1667
                                      acrylonitrile 33
                                        allylidyne group 0
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.