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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Definition:A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an ethenyl group.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 Alpl alkaline phosphatase, liver/bone/kidney 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 4:137,469,042...137,523,695
Ensembl chr 4:137,469,044...137,523,695
JBrowse link
G Apex2 apurinic/apyrimidinic endonuclease 2 increases expression
multiple interactions
ISO 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:149,286,625...149,371,175
Ensembl chr  X:149,302,515...149,372,864
JBrowse link
G Bax BCL2-associated X protein increases expression
multiple interactions
ISO
EXP
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 7:45,111,124...45,116,332
Ensembl chr 7:45,111,121...45,116,322
JBrowse link
G Bcl2 B cell leukemia/lymphoma 2 decreases expression ISO
EXP
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 chr 1:106,465,906...106,642,020
Ensembl chr 1:106,465,908...106,642,004
JBrowse link
G Bcl2l1 BCL2-like 1 decreases expression ISO Acrylonitrile results in decreased expression of BCL2L1 protein CTD PMID:33132245 NCBI chr 2:152,600,652...152,673,632
Ensembl chr 2:152,622,588...152,673,648
JBrowse link
G Becn1 beclin 1, autophagy related increases expression EXP Acrylonitrile results in increased expression of BECN1 mRNA CTD PMID:35429547 NCBI chr11:101,179,084...101,193,112
Ensembl chr11:101,176,778...101,193,112
JBrowse link
G Casp12 caspase 12 increases expression ISO Acrylonitrile results in increased expression of CASP12 protein CTD PMID:33132245 NCBI chr 9:5,345,419...5,373,034
Ensembl chr 9:5,345,430...5,373,032
JBrowse link
G Casp3 caspase 3 increases activity
multiple interactions
increases cleavage
increases expression
ISO
EXP
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 chr 8:47,070,326...47,092,733
Ensembl chr 8:47,070,326...47,092,724
JBrowse link
G Cat catalase decreases activity
multiple interactions
increases expression
ISO
EXP
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 2:103,284,249...103,315,498
Ensembl chr 2:103,284,194...103,315,505
JBrowse link
G Cbs cystathionine beta-synthase decreases expression ISO Acrylonitrile results in decreased expression of CBS protein CTD PMID:33486070 NCBI chr17:31,831,602...31,856,170
Ensembl chr17:31,827,868...31,856,212
JBrowse link
G Ccl2 C-C motif chemokine ligand 2 decreases expression
multiple interactions
increases expression
ISO 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 chr11:81,926,403...81,928,278
Ensembl chr11:81,926,397...81,928,279
JBrowse link
G Ccnd1 cyclin D1 multiple interactions
increases expression
decreases expression
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 7:144,483,668...144,493,568
Ensembl chr 7:144,483,668...144,493,662
JBrowse link
G Ccnd2 cyclin D2 multiple interactions
increases expression
ISO 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 6:127,102,125...127,131,913
Ensembl chr 6:127,102,125...127,129,156
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 7:37,797,409...37,806,915
Ensembl chr 7:37,797,409...37,806,959
JBrowse link
G Cdh1 cadherin 1 decreases expression ISO Acrylonitrile results in decreased expression of CDH1 protein CTD PMID:30236600 NCBI chr 8:107,329,982...107,396,879
Ensembl chr 8:107,329,983...107,396,878
JBrowse link
G Cdh2 cadherin 2 increases expression ISO Acrylonitrile results in increased expression of CDH2 protein CTD PMID:30236600 NCBI chr18:16,721,934...16,942,303
Ensembl chr18:16,721,934...16,942,303
JBrowse link
G Cdkn1a cyclin dependent kinase inhibitor 1A multiple interactions
increases expression
decreases expression
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 chr17:29,309,953...29,319,696
Ensembl chr17:29,309,950...29,319,701
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 6:134,897,364...134,902,488
Ensembl chr 6:134,897,364...134,902,476
JBrowse link
G Cth cystathionine gamma lyase decreases expression ISO Acrylonitrile results in decreased expression of CTH protein CTD PMID:33486070 NCBI chr 3:157,599,885...157,630,718
Ensembl chr 3:157,599,885...157,630,714
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 chr 1:128,515,936...128,520,036
Ensembl chr 1:128,515,936...128,520,030
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
ISO
EXP
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 7:140,343,732...140,354,903
Ensembl chr 7:140,343,652...140,354,900
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 increases expression ISO
EXP
Acrylonitrile results in increased expression of DDIT3 protein
Acrylonitrile results in increased expression of DDIT3 mRNA
CTD PMID:33132245 PMID:35429547 NCBI chr10:127,126,662...127,132,160
Ensembl chr10:127,126,643...127,132,157
Ensembl chr10:127,126,643...127,132,157
JBrowse link
G Eif2s1 eukaryotic translation initiation factor 2, subunit 1 alpha increases expression ISO Acrylonitrile results in increased expression of EIF2S1 protein modified form CTD PMID:33132245 NCBI chr12:78,908,846...78,933,784
Ensembl chr12:78,908,593...78,933,784
JBrowse link
G Fos FBJ osteosarcoma oncogene decreases expression ISO Acrylonitrile results in decreased expression of FOS protein CTD PMID:16173056 NCBI chr12:85,520,664...85,524,048
Ensembl chr12:85,520,664...85,524,047
JBrowse link
G Gpx3 glutathione peroxidase 3 increases expression EXP Acrylonitrile results in increased expression of GPX3 protein CTD PMID:35429547 NCBI chr11:54,793,680...54,801,213
Ensembl chr11:54,793,279...54,801,203
JBrowse link
G H2ax H2A.X variant histone increases expression EXP Acrylonitrile results in increased expression of H2AX protein CTD PMID:35429547 NCBI chr 9:44,246,012...44,247,374
Ensembl chr 9:44,245,991...44,247,374
JBrowse link
G Hmox1 heme oxygenase 1 increases expression ISO Acrylonitrile results in increased expression of HMOX1 protein CTD PMID:14644359 NCBI chr 8:75,820,246...75,827,221
Ensembl chr 8:75,820,249...75,827,217
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:52,076,955...52,110,537
Ensembl chr  X:52,077,014...52,110,536
JBrowse link
G Hspa5 heat shock protein 5 increases expression EXP Acrylonitrile results in increased expression of HSPA5 mRNA CTD PMID:35429547 NCBI chr 2:34,662,102...34,666,541
Ensembl chr 2:34,661,982...34,667,559
JBrowse link
G Il1b interleukin 1 beta multiple interactions
increases expression
ISO 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 2:129,206,490...129,213,059
Ensembl chr 2:129,206,490...129,213,059
JBrowse link
G Il6 interleukin 6 increases expression EXP Acrylonitrile results in increased expression of IL6 protein CTD PMID:35429547 NCBI chr 5:30,218,112...30,224,973
Ensembl chr 5:30,218,112...30,224,979
JBrowse link
G Jun jun proto-oncogene decreases expression ISO Acrylonitrile results in decreased expression of JUN protein CTD PMID:16173056 NCBI chr 4:94,937,273...94,940,459
Ensembl chr 4:94,937,271...94,940,459
JBrowse link
G Map1lc3a microtubule-associated protein 1 light chain 3 alpha increases expression EXP Acrylonitrile results in increased expression of MAP1LC3A mRNA CTD PMID:35429547 NCBI chr 2:155,118,284...155,119,993
Ensembl chr 2:155,118,217...155,119,993
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 chr16:16,801,246...16,865,317
Ensembl chr16:16,801,246...16,865,317
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 7:126,358,798...126,364,988
Ensembl chr 7:126,358,773...126,364,991
JBrowse link
G Mapk8 mitogen-activated protein kinase 8 increases expression EXP Acrylonitrile results in increased expression of MAPK8 mRNA CTD PMID:35429547 NCBI chr14:33,099,855...33,169,213
Ensembl chr14:33,099,855...33,169,115
JBrowse link
G Mpst mercaptopyruvate sulfurtransferase decreases expression ISO Acrylonitrile results in decreased expression of MPST protein CTD PMID:33486070 NCBI chr15:78,290,918...78,298,213
Ensembl chr15:78,290,616...78,298,213
JBrowse link
G Mtor mechanistic target of rapamycin kinase increases expression EXP Acrylonitrile results in increased expression of MTOR mRNA CTD PMID:35429547 NCBI chr 4:148,533,039...148,642,142
Ensembl chr 4:148,533,068...148,642,140
JBrowse link
G Nqo1 NAD(P)H dehydrogenase, quinone 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 chr 8:108,114,856...108,139,012
Ensembl chr 8:108,114,857...108,129,838
JBrowse link
G Ocln occludin decreases expression ISO Acrylonitrile results in decreased expression of OCLN protein CTD PMID:30236600 NCBI chr13:100,633,012...100,689,226
Ensembl chr13:100,633,015...100,689,226
JBrowse link
G Parp1 poly (ADP-ribose) polymerase family, member 1 multiple interactions
increases cleavage
ISO Acetylcysteine inhibits the reaction [Acrylonitrile results in increased cleavage of PARP1 protein] CTD PMID:20981856 NCBI chr 1:180,396,456...180,428,564
Ensembl chr 1:180,396,489...180,428,819
JBrowse link
G Plcb1 phospholipase C, beta 1 affects localization ISO Acrylonitrile affects the localization of PLCB1 protein CTD PMID:12850505 NCBI chr 2:134,628,084...135,317,178
Ensembl chr 2:134,627,987...135,317,178
JBrowse link
G Plcd1 phospholipase C, delta 1 multiple interactions ISO Acrylonitrile results in increased expression of and affects the localization of PLCD1 protein CTD PMID:12850505 NCBI chr 9:118,900,595...118,922,570
Ensembl chr 9:118,900,595...118,922,570
JBrowse link
G Plcg1 phospholipase C, gamma 1 increases expression ISO Acrylonitrile results in increased expression of PLCG1 protein CTD PMID:12850505 NCBI chr 2:160,573,230...160,617,680
Ensembl chr 2:160,573,220...160,617,680
JBrowse link
G Rela v-rel reticuloendotheliosis viral oncogene homolog A (avian) increases expression EXP Acrylonitrile results in increased expression of RELA protein CTD PMID:35429547 NCBI chr19:5,686,993...5,698,162
Ensembl chr19:5,687,511...5,698,158
JBrowse link
G S100a8 S100 calcium binding protein A8 (calgranulin A) decreases expression ISO Acrylonitrile results in decreased expression of S100A8 mRNA CTD PMID:16173056 NCBI chr 3:90,576,378...90,577,341
Ensembl chr 3:90,576,285...90,577,342
JBrowse link
G Snai2 snail family zinc finger 2 increases expression ISO Acrylonitrile results in increased expression of SNAI2 protein CTD PMID:30236600 NCBI chr16:14,523,716...14,527,259
Ensembl chr16:14,523,716...14,527,249
JBrowse link
G Sod1 superoxide dismutase 1, soluble increases expression EXP Acrylonitrile results in increased expression of SOD1 protein CTD PMID:35429547 NCBI chr16:90,017,650...90,023,221
Ensembl chr16:90,017,642...90,023,217
JBrowse link
G Sod2 superoxide dismutase 2, mitochondrial increases expression EXP Acrylonitrile results in increased expression of SOD2 protein CTD PMID:35429547 NCBI chr17:13,226,726...13,237,006
Ensembl chr17:13,225,733...13,258,950
JBrowse link
G Th tyrosine hydroxylase multiple interactions ISO Acrylonitrile inhibits the reaction [3,3'-iminodipropionitrile results in increased expression of TH protein] CTD PMID:19244277 NCBI chr 7:142,446,516...142,453,732
Ensembl chr 7:142,446,489...142,484,865
JBrowse link
G Tnf tumor necrosis factor multiple interactions
increases expression
ISO
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]
Acrylonitrile results in increased expression of TNF protein
CTD PMID:26332274 PMID:35429547 NCBI chr17:35,418,343...35,420,983
Ensembl chr17:35,418,357...35,420,983
JBrowse link
G Trp53 transformation related protein 53 increases expression ISO Acrylonitrile results in increased expression of TP53 protein CTD PMID:33132245 NCBI chr11:69,471,174...69,482,699
Ensembl chr11:69,471,185...69,482,699
JBrowse link
G Xrcc6 X-ray repair complementing defective repair in Chinese hamster cells 6 multiple interactions
increases expression
ISO 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 chr15:81,868,805...81,924,286
Ensembl chr15:81,872,036...81,924,286
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 22178
    role 22194
      biological role 22162
        antimicrobial agent 19546
          antifungal agent 17714
            acrylonitrile 53
              allylidyne group 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 22178
    subatomic particle 22170
      composite particle 22170
        hadron 22201
          baryon 22170
            nucleon 22170
              atomic nucleus 22170
                atom 22170
                  main group element atom 22104
                    p-block element atom 22104
                      carbon group element atom 21904
                        carbon atom 21859
                          organic molecular entity 21830
                            one-carbon compound 18569
                              hydrogen cyanide 4895
                                cyanides 4878
                                  nitrile 4667
                                    aliphatic nitrile 2287
                                      acrylonitrile 53
                                        allylidyne group 0
paths to the root