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

ChEBI IDCHEBI:133973
ChEBI Name(2Z,4E)-3-(2-carboxy-1-hydroxyethyl)-2,4-hexadienedioic acid
Stars
ASCII Name(2Z,4E)-3-(2-carboxy-1-hydroxyethyl)-2,4-hexadienedioic acid
DefinitionA 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.
Last Modified30 November 2016
SubmitterJubra
DownloadsMolfile
FormulaC9H10O7
Net Charge0
Average Mass230.172
Monoisotopic Mass230.04265
SMILESO=C(O)/C=C(/C=C/C(=O)O)C(O)CC(=O)O
InChIInChI=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-
InChIKeyQZBAPOXIHSUTHJ-WFTYEQLWSA-N
Species of MetaboliteComponentSourceComments
Aspergillus niger (ncbitaxon:5061) - PubMed (26040782) The conversion rate was increased 3.5 times by using a coculture of Streptomyces coelicolor and Aspergillus niger.
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
ChEBI Ontology
Outgoing Relation(s)
(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
Citations