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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: 3-chlorocatechol

Synonyms: 3-chlorobenzene-1,2-diol, 3-chloro-1,2-benzenediol

Superclasses: an alcohol a diol a benzenediol a catechol
an aromatic compound a benzenediol a catechol
an aromatic compound a chloroaromatic compound
an organohalogen compound an organochlorine compound a chloroaromatic compound

Chemical Formula: C6H5O2Cl

Molecular Weight: 144.56 Daltons

Monoisotopic Molecular Weight: 143.99780711469998 Daltons

SMILES: C1(C=C(C(=C(C=1)Cl)O)O)

InChI: InChI=1S/C6H5ClO2/c7-4-2-1-3-5(8)6(4)9/h1-3,8-9H

InChIKey: InChIKey=GQKDZDYQXPOXEM-UHFFFAOYSA-N

Unification Links: ChEBI:27715 , ChemSpider:18771 , KEGG:C05618 , PubChem:19928

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -3.3844006 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

3-chlorocatechol degradation I (ortho) , 3-chlorocatechol degradation II (ortho) :
3-chlorocatechol + oxygen → 2-chloro-cis,cis-muconate + 2 H+

3-chlorocatechol degradation III (meta pathway) :
3-chlorocatechol + oxygen → 5-chlorocarbonyl-2-hydroxy-penta-2,4-dienate + H+

Not in pathways:
a catechol + S-adenosyl-L-methionine → a guaiacol + S-adenosyl-L-homocysteine + H+


4 a benzenediol + oxygen → 4 a benzosemiquinone + 2 H2O

Reactions known to produce the compound:

3-chlorobenzoate degradation I (via chlorocatechol) :
3-chloro-3,5-cyclohexadiene-l,2-diol-1-carboxylate + NAD+3-chlorocatechol + CO2 + NADH

chlorinated phenols degradation :
2-chlorophenol + NADPH + oxygen + H+3-chlorocatechol + NADP+ + H2O
3-chlorophenol + NADPH + oxygen + H+3-chlorocatechol + NADP+ + H2O

chlorobenzene degradation :
3-chlorobenzene dihydrodiol + NAD+3-chlorocatechol + NADH + 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+

phosphate acquisition , phosphate utilization in cell wall regeneration :
a phosphate monoester + H2O ↔ an alcohol + phosphate

Not in pathways:
an alcohol + NAD+ + H2O ← an organic hydroperoxide + NADH + H+
an α-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a phosphate monoester + H2O → an alcohol + phosphate
RH + a reduced [NADPH-hemoprotein reductase] + oxygen → ROH + an oxidized [NADPH-hemoprotein reductase] + H2O
an oligosaccharide with β-L-arabinopyranose at the non-reducing end + H2O → β-L-arabinopyranose + an alcohol
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+
a reduced thioredoxin + an organic hydroperoxide → an oxidized thioredoxin + an alcohol + H2O
a 6-O-(β-D-xylopyranosyl)-β-D-glucopyranoside + H2O → β-primeverose + an alcohol
an organic molecule + H2O + 2 oxygen → an alcohol + 2 superoxide + 2 H+
an N5-acyl-L-ornithine-ester + H2O → an N5-acyl-L-ornithine + an alcohol
α-L-fucoside + H2O → L-fucopyranose + an alcohol
a 2-deoxy-α-D-glucoside + H2O → 2-deoxy-D-glucose + an alcohol
a 6-phospho-β-D-galactoside + H2O → α-D-galactose 6-phosphate + an alcohol

In Reactions of unknown directionality:

Not in pathways:
RH + chloride + hydrogen peroxide + H+ = RCl + 2 H2O
an organic molecule + hypochlorous acid = an organochlorine compound + H2O


an alcohol + 3'-phosphoadenylyl-sulfate = adenosine 3',5'-bisphosphate + an organosulfate + H+
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
an alcohol + NADP+ = an aldehyde + NADPH + H+
trans-cinnamoyl-β-D-glucoside + an alcohol = β-D-glucose + alkyl cinnamate
an alcohol + acetyl-CoA = an acetic ester + coenzyme A
2 protein cysteines + an organic hydroperoxide = a protein disulfide + an alcohol + H2O
an organic molecule + an organic hydroperoxide = 2 an alcohol
an organic molecule + hydrogen peroxide = an alcohol + H2O

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

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


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

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 Fri Nov 28, 2014, biocyc11.