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Escherichia coli K-12 substr. MG1655 Compound: 2,3-dihydroxybenzoate

Synonyms: 2,3-dihydroxybenzoic acid, 3-hydroxysalicylate, catechol-3-carboxylate, 2-pyrocatechuate

Superclasses: an acid all carboxy acids a carboxylate an aromatic carboxylate
an alcohol a diol a benzenediol a catechol
an aromatic compound a benzenediol a catechol
an aromatic compound an aromatic carboxylate

Chemical Formula: C7H5O4

Molecular Weight: 153.11 Daltons

Monoisotopic Molecular Weight: 154.026608681 Daltons

SMILES: C(C1(=CC=CC(=C1O)O))([O-])=O

InChI: InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)/p-1

InChIKey: InChIKey=GLDQAMYCGOIJDV-UHFFFAOYSA-M

Unification Links: CAS:303-38-8 , ChEBI:36654 , ChemSpider:5323089 , HMDB:HMDB00397 , IAF1260:34227 , KEGG:C00196 , PubChem:54675818

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -132.01

Reactions known to consume the compound:

enterobactin biosynthesis :
6 ATP + 3 L-serine + 3 2,3-dihydroxybenzoate → 6 AMP + enterobactin + 6 diphosphate + 3 H+

Not in pathways:
ATP + 2,3-dihydroxybenzoate + H+ → 2,3-dihydroxybenzoyl-AMP + diphosphate
2,3-dihydroxybenzoate[periplasmic space] + oxygen[periplasmic space] → 2-carboxymuconate[periplasmic space] + 2 H+[periplasmic space]

Reactions known to produce the compound:

2,3-dihydroxybenzoate biosynthesis :
(2S,3S)-2,3-dihydroxy-2,3-dihydrobenzoate + NAD+2,3-dihydroxybenzoate + NADH + H+

Not in pathways:
aryl-EntB + H2O → EntB isochorismatase / aryl-carrier protein + 2,3-dihydroxybenzoate


a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
a 1-lysophosphatidylcholine + H2O → a carboxylate + sn-glycero-3-phosphocholine + H+

β-D-glucuronide and D-glucuronate degradation :
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol

glycerophosphodiester degradation :
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+


an alcohol + NAD+ + H2O ← an organic hydroperoxide + NADH + H+
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acetic ester + H2O → an alcohol + acetate + H+
an organic hydroperoxide + a reduced thioredoxin → an alcohol + an oxidized thioredoxin + H2O
a phosphate monoester[periplasmic space] + H2O[periplasmic space]an alcohol[periplasmic space] + phosphate[periplasmic space]
a phosphate monoester[periplasmic space] + H2O[periplasmic space]an alcohol[periplasmic space] + phosphate[periplasmic space]

In Reactions of unknown directionality:

Not in pathways:
EntB isochorismatase / aryl-carrier protein + 2,3-dihydroxybenzoate + ATP = aryl-EntB + AMP + diphosphate


an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]


an alcohol + NADP+ = an aldehyde + NADPH + H+

Enzymes activated by 2,3-dihydroxybenzoate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: phosphoenolpyruvate carboxylase [Izui83]

In Growth Media: Neidhardt EZ rich defined medium


References

Izui83: Izui K, Matsuda Y, Kameshita I, Katsuki H, Woods AE (1983). "Phosphoenolpyruvate carboxylase of Escherichia coli. Inhibition by various analogs and homologs of phosphoenolpyruvate." J Biochem (Tokyo) 1983;94(6);1789-95. PMID: 6368527


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 18.5 on Mon Dec 22, 2014, biocyc14.