CHEBI:17947 - 3-dehydroquinic acid

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ChEBI Name 3-dehydroquinic acid
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
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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
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.
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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)
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
DB03868 DrugBank
HMDB0012710 HMDB
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Registry Number Type Source
2115114 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11603966 PubMed citation Europe PMC
13198937 PubMed citation Europe PMC
14269300 PubMed citation Europe PMC
14524706 PubMed citation Europe PMC
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).