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MetaCyc Compound: 3-dehydroquinate

Synonyms: 3-dehydroquinic acid, 5-dehydroquinic acid, 5-dehydroquinate, 5-de-H-quinate

The numbering system used in the naming of 3-dehydroquinate is that of the recommendations on cyclitols, sections I-8 and I-9. The use of the term '5-dehydroquinate' for this compound is based on an earlier system of numbering.

Chemical Formula: C7H9O6

Molecular Weight: 189.14 Daltons

Monoisotopic Molecular Weight: 190.0477380536 Daltons

3-dehydroquinate compound structure

SMILES: C1(C(O)C(O)C(=O)CC(O)(C([O-])=O)1)

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)/p-1/t3-,5+,7-/m1/s1


Unification Links: CAS:10534-44-8, ChEBI:32364, ChemSpider:4573866, HMDB:HMDB12710, IAF1260:36436, KEGG:C00944, PubChem:5460271

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -122.361984Inferred by computational analysis [Latendresse13]

Reactions known to produce the compound:

3-dehydroquinate biosynthesis I :
3-deoxy-D-arabino-heptulosonate-7-phosphate → 3-dehydroquinate + phosphate

3-dehydroquinate biosynthesis II (archaea) :
2-amino-3,7-dideoxy-D-threo-hept-6-ulosonate + NAD+ + H2O → 3-dehydroquinate + ammonium + NADH + H+

quinate degradation I :
L-quinate + a quinone → 3-dehydroquinate + a quinol

quinate degradation II :
L-quinate + NAD+3-dehydroquinate + NADH + H+

Reactions known to both consume and produce the compound:

chorismate biosynthesis from 3-dehydroquinate , gallate biosynthesis , quinate degradation I , quinate degradation II :
3-dehydroquinate ↔ 3-dehydroshikimate + H2O

In Reactions of unknown directionality:

Not in pathways:
L-quinate + NAD(P)+ = 3-dehydroquinate + NAD(P)H + H+

Enzymes inhibited by 3-dehydroquinate, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: 3-dehydroquinate dehydratase [Chaudhuri86]


Chaudhuri86: Chaudhuri S, Lambert JM, McColl LA, Coggins JR (1986). "Purification and characterization of 3-dehydroquinase from Escherichia coli." Biochem J 1986;239(3);699-704. PMID: 2950851

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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