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MetaCyc Compound: 3-methylcatechol

Synonyms: 2,3-dihydroxytoluene

Superclasses: an alcohol a diol a benzenediol a catechol
an aromatic compound a benzenediol a catechol

Chemical Formula: C7H8O2

Molecular Weight: 124.14 Daltons

Monoisotopic Molecular Weight: 124.05242950099999 Daltons

SMILES: CC1(=CC=CC(=C1O)O)

InChI: InChI=1S/C7H8O2/c1-5-3-2-4-6(8)7(5)9/h2-4,8-9H,1H3

InChIKey: InChIKey=PGSWEKYNAOWQDF-UHFFFAOYSA-N

Unification Links: CAS:488-17-5 , ChEBI:18404 , ChemSpider:333 , DrugBank:DB03454 , KEGG:C02923 , MetaboLights:MTBLC18404 , PubChem:340

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 31.15897 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

2-nitrotoluene degradation , toluene degradation to 2-oxopent-4-enoate (via toluene-cis-diol) , toluene degradation to 2-oxopent-4-enoate I (via o-cresol) :
3-methylcatechol + oxygen → cis,cis-2-hydroxy-6-oxohepta-2,4-dienoate + H+

Not in pathways:
3-methylcatechol + oxygen → 2-hydroxy-6-oxohepta-2,4-dienoate + H+


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:

2-nitrotoluene degradation :
2-nitrotoluene + H+ + oxygen → 3-methylcatechol + nitrite

toluene degradation to 2-oxopent-4-enoate (via toluene-cis-diol) :
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+3-methylcatechol + NADH + H+

toluene degradation to 2-oxopent-4-enoate I (via o-cresol) :
2-methylphenol + NADH + H+ + oxygen → 3-methylcatechol + NAD+ + H2O

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:
1,2-dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate + NAD+ = CO2 + 3-methylcatechol + NADH


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

Inhibitor (Competitive) of: 1,2-dihydroxynaphthalene dioxygenase [Patel80]


References

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

Patel80: Patel TR, Barnsley EA (1980). "Naphthalene metabolism by pseudomonads: purification and properties of 1,2-dihydroxynaphthalene oxygenase." J Bacteriol 143(2);668-73. PMID: 7204331


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 Jan 26, 2015, biocyc12.