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Term:2-(3,4-dihydroxyphenyl)-2-oxoethyl thiocyanate
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Accession:CHEBI:85310 term browser browse the term
Definition:A member of the class of thiocyanates that is 3,4-dihydroxyacetophenone in which one of the methyl hydrogens has been replaced by the sulfur of a cyanosulfanediyl (-SC#N) group. It has been found to induce the expression of the endoplasmic reticulum chaperone protein GRP78 (78 kDa glucose-regulated protein, BiP, a highly conserved member of the 70 kDa heat shock protein family) leading to an attenuation of the unfolded protein response. It protects neuronal cells and retinal cells from endoplasmic reticulum (ER)-stress induced cell death.
Synonyms:related_synonym: 1-(3,4-dihydroxyphenyl)-2-thiocyanate-ethanone;   BIX;   BiP inducer X;   Formula=C9H7NO3S;   InChI=1S/C9H7NO3S/c10-5-14-4-9(13)6-1-2-7(11)8(12)3-6/h1-3,11-12H,4H2;   InChIKey=SVFLBLCWKKQKDW-UHFFFAOYSA-N;   SMILES=Oc1ccc(cc1O)C(=O)CSC#N;   immunoglobulin heavy-chain binding protein inducer X
 xref: PMID:18049481 "SUBMITTER";   PMID:20857693 "Europe PMC";   PMID:23216380 "Europe PMC";   Reaxys:3292146 "Reaxys"

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Term Annotations click to browse term
  CHEBI ontology 19748
    role 19695
      chemical role 19211
        donor 18322
          Bronsted acid 18173
            hydracid 5843
              thiocyanic acid 0
                thiocyanates 0
                  2-(3,4-dihydroxyphenyl)-2-oxoethyl thiocyanate 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19748
    subatomic particle 19744
      composite particle 19744
        hadron 19744
          baryon 19744
            nucleon 19744
              atomic nucleus 19744
                atom 19744
                  main group element atom 19628
                    p-block element atom 19628
                      carbon group element atom 19522
                        carbon atom 19516
                          organic molecular entity 19516
                            organic group 18426
                              organic divalent group 18418
                                organodiyl group 18418
                                  carbonyl group 18306
                                    carbonyl compound 18306
                                      ketone 15922
                                        aromatic ketone 11829
                                          2-(3,4-dihydroxyphenyl)-2-oxoethyl thiocyanate 0
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.