ChEBI logo

ChEBI


    The database and ontology of Chemical Entities of Biological Interest

spacer

3-dehydroquinic acid (CHEBI:17947)

Search for only All in ChEBI

Main     ChEBI Ontology     Automatic Xrefs      
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
See structure as:  Image  Applet
Save molfile Download Molfile
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula Source
C7H10O6 KEGG COMPOUND
Net Charge 0
Average Mass 190.15070
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 on the 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 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
Database Links Databases
3-Dehydroquinic_acid Wikipedia
C00944 KEGG COMPOUND
DB03868 DrugBank
DEHYDROQUINATE MetaCyc
DQA PDBeChem
HMDB12710 HMDB
View more database links
Registry Number Type Source
2115114 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11603966 PubMed citation CiteXplore
13198937 PubMed citation CiteXplore
14269300 PubMed citation CiteXplore
14524706 PubMed citation CiteXplore
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).
 
Last Modified
02 April 2014

spacer
spacer