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MetaCyc Compound: formaldehyde

Synonyms: formalin, methanal, formol

Superclasses: an aldehyde or ketone an aldehyde an n-alkanal

Chemical Formula: CH2O

Molecular Weight: 30.026 Daltons

Monoisotopic Molecular Weight: 30.0105646863 Daltons

formaldehyde compound structure

SMILES: [CH2]=O

InChI: InChI=1S/CH2O/c1-2/h1H2

InChIKey: InChIKey=WSFSSNUMVMOOMR-UHFFFAOYSA-N

Unification Links: CAS:50-00-0 , ChEBI:16842 , ChemSpider:692 , DrugBank:DB03843 , HMDB:HMDB01426 , IAF1260:33726 , KEGG:C00067 , MetaboLights:MTBLC16842 , PubChem:712

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -10.65776 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

4-hydroxycoumarin and dicoumarol biosynthesis :
2 4-hydroxycoumarin + formaldehyde → dicoumarol + H2O

formaldehyde assimilation I (serine pathway) :
formaldehyde + a tetrahydrofolate → a 5,10-methylene-tetrahydrofolate + H2O

formaldehyde assimilation II (RuMP Cycle) , formaldehyde oxidation I :
hexulose 6-phosphate ← D-ribulose 5-phosphate + formaldehyde

formaldehyde assimilation III (dihydroxyacetone cycle) :
formaldehyde + D-xylulose 5-phosphate → dihydroxyacetone + D-glyceraldehyde 3-phosphate

formaldehyde oxidation III (mycothiol-dependent) :
formaldehyde + mycothiol → S-hydroxymethylmycothiol

formaldehyde oxidation IV (thiol-independent) , methanol oxidation to carbon dioxide :
formaldehyde + NAD+ + H2O → formate + NADH + 2 H+

formaldehyde oxidation V (H4MPT pathway) :
5,10-methylene-tetrahydromethanopterin + H2O ← formaldehyde + tetrahydromethanopterin

furaneol biosynthesis :
norfuraneol + formaldehyde → 4-hydroxy-5-methyl-2-methylene-3(2H)-furanone + H2O

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+

Not in pathways:
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+

Reactions known to produce the compound:

5,5'-dehydrodivanillate degradation :
5,5'-dehydrodivanillate + NADH + oxygen + H+ → 2,2',3-trihydroxy-3'-methoxy-5,5'-dicarboxybiphenyl + formaldehyde + NAD+ + H2O

caffeine degradation III (bacteria, via demethylation) :
7-methylxanthine + NAD(P)H + oxygen + H+ → xanthine + formaldehyde + NAD(P)+ + H2O
caffeine + NAD(P)H + oxygen + H+ → theobromine + formaldehyde + NAD(P)+ + H2O
paraxanthine + NAD(P)H + oxygen + H+ → 7-methylxanthine + formaldehyde + NAD(P)+ + H2O
theobromine + NAD(P)H + oxygen + H+ → 7-methylxanthine + formaldehyde + NAD(P)+ + H2O
caffeine + NAD(P)H + oxygen + H+ → paraxanthine + formaldehyde + NAD(P)+ + H2O

colchicine biosynthesis :
demecolcine + NADPH + oxygen + H+ → deacetylcolchicine + formaldehyde + NADP+ + H2O

creatinine degradation I :
sarcosine + oxygen + H2O → glycine + formaldehyde + hydrogen peroxide
sarcosine + an oxidized electron-transfer flavoprotein + H2O + H+ → glycine + formaldehyde + a reduced electron-transfer flavoprotein

creatinine degradation II :
sarcosine + oxygen + H2O → glycine + formaldehyde + hydrogen peroxide
sarcosine + an oxidized electron-transfer flavoprotein + H2O + H+ → glycine + formaldehyde + a reduced electron-transfer flavoprotein

dimethyl sulfide degradation I :
methanethiol + oxygen + H2O → formaldehyde + hydrogen sulfide + hydrogen peroxide
dimethyl sulfide + NADH + oxygen + H+ → methanethiol + formaldehyde + NAD+ + H2O

dimethyl sulfide degradation II (oxidation) :
methanesulfonate + NADH + oxygen → formaldehyde + sulfite + NAD+ + H2O
dimethyl sulfone + 2 FMNH2 + 2 oxygen → methanesulfonate + formaldehyde + 2 FMN + 2 H2O + 3 H+

glycine betaine degradation I :
sarcosine + oxygen + H2O → glycine + formaldehyde + hydrogen peroxide
dimethylglycine + an oxidized electron-transfer flavoprotein + H2O + H+ → sarcosine + formaldehyde + a reduced electron-transfer flavoprotein

L-proline betaine degradation :
L-proline betaine + NAD(P)H + oxygen + H+N-methyl-L-proline + formaldehyde + NAD(P)+ + H2O
N-methyl-L-proline + oxygen + H2O → L-proline + formaldehyde + hydrogen peroxide

melatonin degradation I :
melatonin + a reduced flavoprotein + oxygen → N-acetyl-serotonin + an oxidized flavoprotein + formaldehyde + H2O

methanesulfonate degradation :
methanesulfonate + NADH + oxygen → formaldehyde + sulfite + NAD+ + H2O

methanol oxidation to carbon dioxide , methanol oxidation to formaldehyde II :
methanol + NAD+formaldehyde + NADH + H+

methanol oxidation to formaldehyde I :
methanol + 2 an oxidized cytochrome cLformaldehyde + 2 a reduced cytochrome cL + 2 H+

methanol oxidation to formaldehyde III :
methanol + an oxidized unknown electron acceptor → formaldehyde + an reduced unknown electron acceptor

methanol oxidation to formaldehyde IV :
methanol + oxygen → hydrogen peroxide + formaldehyde

Reactions known to both consume and produce the compound:

formaldehyde oxidation II (glutathione-dependent) :
S-hydroxymethylglutathione → formaldehyde + glutathione

Not in pathways:
a primary alcohol + NAD+an aldehyde + NADH + H+

In Reactions of unknown directionality:

Not in pathways:
erythrulose 1-phosphate = formaldehyde + glycerone phosphate
bromochloromethane + H2O = bromide + chloride + formaldehyde + 2 H+
N,N-dimethylaniline-N-oxide = formaldehyde + N-methylaniline
dichloromethane + H2O = formaldehyde + 2 chloride + 2 H+
methanol + hydrogen peroxide = formaldehyde + 2 H2O
2-dehydropantoate = formaldehyde + 3-methyl-2-oxobutanoate
dimethylamine + an oxidized electron-transfer flavoprotein + H2O + H+ = formaldehyde + methylamine + a reduced electron-transfer flavoprotein
trimethylamine + an oxidized electron-transfer flavoprotein + H2O + H+ = dimethylamine + formaldehyde + a reduced electron-transfer flavoprotein
2 formaldehyde + H2O = methanol + formate + H+
pyruvate + formaldehyde + H+ = acetol + CO2

Not in pathways:
an n-alkanal + NAD(P)+ = an alk-2-enal + NAD(P)H + H+
an n-alkanal + NADP+ = an alk-2-enal + NADPH + H+

Not in pathways:
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a primary alcohol + 2 an oxidized cytochrome cL = an aldehyde + 2 a reduced cytochrome cL + 2 H+
an aliphatic amine + an oxidized cytochrome c550 + H2O = an aldehyde + ammonium + a reduced cytochrome c550
an alkylamine + 2 an oxidized cytochrome c550 + H2O = an aldehyde + ammonium + 2 a reduced cytochrome c550
a 2-oxo carboxylate + H+ = an aldehyde + CO2
an alcohol + NADP+ = an aldehyde + NADPH + H+
a primary alcohol + an oxidized unknown electron acceptor = an aldehyde + an reduced unknown electron acceptor
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
a primary alcohol + an oxidized azurin = an aldehyde + a reduced azurin

Enzymes inhibited by formaldehyde, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: 3-methyl-2-oxobutanoate hydroxymethyltransferase [Powers76, Comment 1] , methylglutamate dehydrogenase [Bamforth77] , 2-protocatechuoylphloroglucinolcarboxylate esterase [Child63] , rutinase [HAY61] , aspartate-semialdehyde dehydrogenase [Peters90]

This compound has been characterized as an alternative substrate of the following enzymes: methanol:N,N-dimethyl-4-nitrosoaniline oxidoreductase , 2-aminomuconate-semialdehyde dehydrogenase , fuculose-1-phosphate aldolase , methylglyoxal oxidase , alcohol oxidase , D-glyceraldehyde dehydrogenase , NAD+ L-lactaldehyde dehydrogenase , 2-hydroxymuconate 6-semialdehyde dehydrogenase , rhamnulose-1-phosphate aldolase , glutarate semialdehyde dehydrogenase


References

Bamforth77: Bamforth CW, Large PJ (1977). "Solubilization, partial purification and properties of N-methylglutamate dehydrogenase from Pseudomonas aminovorans." Biochem J 161(2);357-70. PMID: 15545

Child63: Child JJ, Simpson FJ, Westlake DWS (1963). "Degradation of rutin by Aspergillus flavus. Production, purification and characterization of an esterase." Can J Microbiol 9:653-664.

HAY61: HAY GW, WESTLAKE DW, SIMPSON FJ (1961). "Degradation of rutin by Aspergillus flavus. Purification and characterization of rutinase." Can J Microbiol 7;921-32. PMID: 13905544

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

Peters90: Peters, P, Galinski, EA, Truper, HG "The biosynthesis of ectoine." FEMS Microbiology Letters 71:157-162 (1990).

Powers76: Powers SG, Snell EE (1976). "Ketopantoate hydroxymethyltransferase. II. Physical, catalytic, and regulatory properties." J Biol Chem 1976;251(12);3786-93. PMID: 6463


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 19.0 on Tue Sep 1, 2015, biocyc11.