CHEBI:133973 - (2Z,4E)-3-(2-carboxy-1-hydroxyethyl)-2,4-hexadienedioic acid

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ChEBI Name (2Z,4E)-3-(2-carboxy-1-hydroxyethyl)-2,4-hexadienedioic acid ChEBI ID CHEBI:133973 ChEBI ASCII Name (2Z,4E)-3-(2-carboxy-1-hydroxyethyl)-2,4-hexadienedioic acid Definition A tricarboxylic acid that is hexa-2,4-dienedioic acid which is substituted at position 3 by a 2-carboxy-1-hydroxyethyl group (the 2Z,4E isomer; a mixture of isomers at the carbon bearing the alcoholic hydroxy group). It has been produced from trans-caffeic acid using Aspergillus niger, but the conversion rate was increased 3.5 times by using a coculture of Streptomyces coelicolor and Aspergillus niger. Stars This entity has been manually annotated by the ChEBI Team. Submitter Julian Brandl Supplier Information Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C9H10O7 Net Charge 0 Average Mass 230.172 Monoisotopic Mass 230.04265 InChI InChI=1S/C9H10O7/c10-6(4-9(15)16)5(3-8(13)14)1-2-7(11)12/h1-3,6,10H,4H2,(H,11,12)(H,13,14)(H,15,16)/b2-1+,5-3- InChIKey QZBAPOXIHSUTHJ-WFTYEQLWSA-N SMILES C(/C=C(/C=C/C(O)=O)\C(CC(=O)O)O)(O)=O Metabolite of Species Details Aspergillus niger (NCBI:txid5061) The conversion rate was increased 3.5 times by using a coculture of Streptomyces coelicolor and Aspergillus niger. See: PubMed Roles Classification Chemical Role(s): Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid ) Biological Role(s): Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus . View more via ChEBI Ontology ChEBI Ontology Outgoing (2Z,4E)-3-(2-carboxy-1-hydroxyethyl)-2,4-hexadienedioic acid (CHEBI:133973) has role Aspergillus metabolite (CHEBI:76956) (2Z,4E)-3-(2-carboxy-1-hydroxyethyl)-2,4-hexadienedioic acid (CHEBI:133973) is a olefinic compound (CHEBI:78840) (2Z,4E)-3-(2-carboxy-1-hydroxyethyl)-2,4-hexadienedioic acid (CHEBI:133973) is a secondary alcohol (CHEBI:35681) (2Z,4E)-3-(2-carboxy-1-hydroxyethyl)-2,4-hexadienedioic acid (CHEBI:133973) is a tricarboxylic acid (CHEBI:27093) IUPAC Name (2E,4Z)-4-(carboxymethylene)-5-hydroxyhept-2-enedioic acid Citation Type Source 26040782 PubMed citation SUBMITTER Last Modified 30 November 2016

General Comment 2016-11-28 Note that in Scientific Reports, 2015, 5, 10868 (PMID:26040782, DOI: 10.1038/srep10868) the structure shown for this entity (compound (1) in Figure 4) is correct but the name is incorrect - the stereochemistry of the double bonds should be (2Z,4E), not (2E,4E). We thank Dr. Young Hae Choi of the Natural Products Laboratory at the Institute of Biology, Leiden University for the clarification.