CHEBI:17947 - 3-dehydroquinic acid

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ChEBI Name 3-dehydroquinic acid ChEBI ID CHEBI:17947 Definition A 4-oxo monocarboxylic acid derived from quinic acid by oxidation of the hydroxy group at position 3 to the corresponding keto group. Stars This entity has been manually annotated by the ChEBI Team. Secondary ChEBI IDs CHEBI:42078, CHEBI:1487, CHEBI:19997 Supplier Information ZINC000004095505 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License 3-Dehydroquinic acid (DHQ) is the first carbocyclic intermediate of the shikimate pathway. It is created from 3-deoxyarabinoheptulosonate 7-phosphate, a 7-carbon ulonic acid, by the enzyme DHQ synthase. The mechanism of ring closure is complex, but involves an aldol condensation at C-2 and C-7. It has the same structure as quinic acid, which is found in coffee, but the C-3 hydroxyl is oxidized to a ketone group. 3-Dehydroquinic acid undergoes five further enzymatic steps in the remainder of the shikimate pathway to chorismic acid, a precursor to tyrosine, 3-phenylalanine, tryptophan, and some vitamins, including: Vitamin K Pteroylmonoglutamic acid, called folate. 3-Dehydroquinate can also be a precursor to pyrroloquinoline quinone (PQQ), an alternate redox coenzyme involved in oxidative phosphorylation. Read full article at Wikipedia Formula C7H10O6 Net Charge 0 Average Mass 190.15070 Monoisotopic Mass 190.04774 InChI InChI=1S/C7H10O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3,5,8,10,13H,1-2H2,(H,11,12)/t3-,5+,7-/m1/s1 InChIKey WVMWZWGZRAXUBK-SYTVJDICSA-N SMILES O[C@@H]1C[C@@](O)(CC(=O)[C@H]1O)C(O)=O 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): Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. View more via ChEBI Ontology ChEBI Ontology Outgoing 3-dehydroquinic acid (CHEBI:17947) has functional parent (−)-quinic acid (CHEBI:17521) 3-dehydroquinic acid (CHEBI:17947) has role Escherichia coli metabolite (CHEBI:76971) 3-dehydroquinic acid (CHEBI:17947) is a 2-hydroxy monocarboxylic acid (CHEBI:49302) 3-dehydroquinic acid (CHEBI:17947) is a 4-hydroxy monocarboxylic acid (CHEBI:35970) 3-dehydroquinic acid (CHEBI:17947) is a 4-oxo monocarboxylic acid (CHEBI:35950) 3-dehydroquinic acid (CHEBI:17947) is a 5-hydroxy monocarboxylic acid (CHEBI:37125) 3-dehydroquinic acid (CHEBI:17947) is a secondary α-hydroxy ketone (CHEBI:2468) 3-dehydroquinic acid (CHEBI:17947) is conjugate acid of 3-dehydroquinate (CHEBI:32364) Incoming 3-dehydroquinate (CHEBI:32364) is conjugate base of 3-dehydroquinic acid (CHEBI:17947) IUPAC Name rel-(1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexanecarboxylic acid Synonyms Sources 3-Dehydroquinic acid KEGG COMPOUND 5-Dehydroquinic acid KEGG COMPOUND Manual Xrefs Databases 3-Dehydroquinic_acid Wikipedia C00019664 KNApSAcK C00944 KEGG COMPOUND DB03868 DrugBank DEHYDROQUINATE MetaCyc DQA PDBeChem HMDB0012710 HMDB View more database links Registry Number Type Source 2115114 Reaxys Registry Number Reaxys Citations Last Modified 06 February 2018

General Comment 2005-03-09 The numbering system used for 3-dehydroquinic acid is that of the IUPAC/CBN recommendations on cyclitols, sections I-8 and I-9. The use of the term '5-dehydroquinic acid' for this compound is based on an earlier system of numbering (for example of use, see S. Mitsuhashi and B. D. Davis, Biochim. Biophys. Acta, 1954, 15, 268-280).