Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

MetaCyc Compound: 3-dehydroquinate

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

Summary:
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

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

InChIKey: InChIKey=WVMWZWGZRAXUBK-SYTVJDICSA-M

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

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

Reactions known to produce the compound:

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:

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

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]


References

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."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Mon Nov 24, 2014, BIOCYC13B.