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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:ochratoxin B
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Accession:CHEBI:141524 term browser browse the term
Definition:A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid. Ochratoxin B differs from the more naturally abundant ochratoxin A in the absence of the dihydroisocoumarin chlorine atom. It has cytotoxic effects on kidney and liver cells in vitro but only minor effects in vivo, due to its rapid metabolism and excretion. It inhibits cell proliferation of human liver HepG2 cells at doses as low as 1 mug/ ml but lacks the genotoxic activity of ochratoxin A, even at higher concentrations.
Synonyms:exact_synonym: N-[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]-L-phenylalanine
 related_synonym: (2S)-2-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]amino}-3-phenylpropanoic acid;   Formula=C20H19NO6;   InChI=1S/C20H19NO6/c1-11-9-13-7-8-14(17(22)16(13)20(26)27-11)18(23)21-15(19(24)25)10-12-5-3-2-4-6-12/h2-8,11,15,22H,9-10H2,1H3,(H,21,23)(H,24,25)/t11-,15+/m1/s1;   InChIKey=DAEYIVCTQUFNTM-ABAIWWIYSA-N;   N-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]carbonyl}-L-phenylalanine;   OTB;   SMILES=C1=CC=CC=C1C[C@@H](C(=O)O)NC(=O)C2=CC=C3C(=C2O)C(O[C@@H](C3)C)=O
 xref: Beilstein:1300160;   CAS:4825-86-9
 xref_mesh: MESH:C045354
 xref: PMID:15623466;   PMID:15963343;   PMID:17161512;   PMID:22069651;   PMID:22331050;   PMID:24968897;   PMID:26133228;   PMID:28749978;   PMID:29428592;   PMID:299;   PMID:33338836;   PMID:879783;   Reaxys:1300160



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Term Annotations click to browse term
  CHEBI ontology 20056
    role 20008
      biological role 20007
        poison 18483
          toxin 15294
            mycotoxin 11906
              ochratoxin B 0
Path 2
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  CHEBI ontology 20056
    subatomic particle 20054
      composite particle 20054
        hadron 20054
          baryon 20054
            nucleon 20054
              atomic nucleus 20054
                atom 20054
                  main group element atom 19956
                    main group molecular entity 19956
                      s-block molecular entity 19752
                        hydrogen molecular entity 19745
                          hydrides 19114
                            organic hydride 18653
                              organic fundamental parent 18653
                                hydrocarbon 18389
                                  cyclic hydrocarbon 17191
                                    monocyclic hydrocarbon 6050
                                      annulene 5697
                                        aromatic annulene 5697
                                          benzene 5697
                                            alkylbenzene 3395
                                              methylbenzene 3260
                                                toluene 3125
                                                  benzyl group 2540
                                                    phenylalanine 2540
                                                      L-phenylalanine 2283
                                                        L-phenylalanine derivative 2270
                                                          N-acyl-L-phenylalanine 1332
                                                            ochratoxin B 0
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