Ligand formaldehyde

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Basic Ligand Information

Molecular Structure

CH₂O

formaldehyde

WSFSSNUMVMOOMR-UHFFFAOYSA-N

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Synonyms:

carbonmonoxide, CH2O, CHOH, formalin, HCHO, methanal

Related pathways

BRENDA

creatinine degradation, formaldehyde oxidation, methane metabolism, methanogenesis from CO2, morphine biosynthesis

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KEGG

Carbon metabolism, Chloroalkane and chloroalkene degradation, Methane metabolism, Microbial metabolism in diverse environments

MetaCyc

(-)-4'-demethyl-epipodophyllotoxin biosynthesis, 12-epi-fischerindole biosynthesis, 12-epi-hapalindole biosynthesis, 3-[(E)-2-isocyanoethenyl]-1H-indole biosynthesis, 4-hydroxycoumarin and dicoumarol biosynthesis

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Show all BRENDA pathways known for formaldehyde

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (23 results)

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1.1.1.244

formaldehyde + NADH + H+ = methanol + NAD+

formaldehyde + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + NAD+ = S-formylmycothiol + NADH

288322, 288324, 288323

1.1.3.13

formaldehyde + O2 = formic acid + H2O2

672302

1.2.1.10

formaldehyde + CoA + NAD+ = formyl-CoA + NADH + H+

695594

4LRS, 3D-view

1.2.1.3

formaldehyde + NAD+ + H2O = formate + NADH

711651

1.2.1.4

formaldehyde + NADP+ = formate + NADPH + H+

formaldehyde + ferricytochrome b559/569 complex = formate + ferrocytochrome b559/569 complex

288469

1.2.7.5

formaldehyde + H2O + oxidized ferredoxin = formate + H+ + reduced ferredoxin

722823, 722893

1.2.7.B2

formaldehyde + H2O + oxidized ferredoxin = formate + H+ + reduced ferredoxin

tetrahydrofolate + HCHO + dUMP = dihydrofolate + dTMP + H2O

5,6,7,8-tetrahydromethanopterin + formaldehyde = 5,10-methylenetetrahydromethanopterin + H2O

725231, 727849, 758451

4.4.1.22

5,6,7,8-tetrahydromethanopterin + formaldehyde = 5,10-methylenetetrahydromethanopterin + H2O

749071

In Vivo Product in Enzyme-catalyzed Reactions (235 results)

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1.1.1.244

methanol + NAD+ = formaldehyde + NADH + H+

286372, 286373, 286374, 286375, -

1.1.1.71

methanol + NAD(P)+ = formaldehyde + NAD(P)H + H+

methanol + 2 cytochrome c = formaldehyde + 2 reduced cytochrome c

1.1.2.B2

methanol + ferricytochrome c551i = formaldehyde + ferrocytochrome c551i

1.1.3.13

methanol + O2 = formaldehyde + H2O2

1.1.99.36

methanol + N,N-dimethyl-4-nitrosoaniline = formaldehyde + 4-(hydroxylamino)-N,N-dimethylaniline

N6-methyladenine in DNA + 2-oxoglutarate + O2 = adenine in DNA + formaldehyde + succinate + CO2

dimethylamine + NADPH + H+ + O2 = methylamine + formaldehyde + NADP+ + H2O

1,1-dimethylhydrazine + NADPH + O2 = formaldehyde + CH3N2H3 + NADP+

methanesulfonate + FMNH2 + O2 = formaldehyde + FMN + sulfite + H2O

1.14.14.35

dimethyl sulfone + FMNH2 + O2 = methanesulfinate + formaldehyde + FMN + H2O

1.14.14.5

methanesulfonate + FMNH2 + O2 = formaldehyde + FMN + sulfite + H2O

formate + NADH + 2 H+ = formaldehyde + NAD+ + H2O

1.2.98.1

formate + methanol = formaldehyde

1.4.3.21

methylamine + H2O + O2 = formaldehyde + NH3 + H2O2

N,N-dimethylglycine + H2O + O2 = sarcosine + formaldehyde + H2O2

394961, 394957, -

1.5.3.4

epsilon-N-methyl groups in protein-bound methyllysine residues + O2 + H2O = demethylated lysine residues + formaldehyde + H2O2

N-methyl-L-glutamate + acceptor + H2O = L-glutamate + formaldehyde + reduced acceptor

1.8.3.4

2 entries

4.1.2.32

Trimethylamine N-oxide = Dimethylamine + formaldehyde

653047, -

4.1.2.43

D-arabino-hex-3-ulose 6-phosphate = D-ribulose 5-phosphate + formaldehyde

4.1.99.24

L-tyrosine + D-ribulose 5-phosphate = (2S)-3-(4-hydroxyphenyl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O

4.1.99.25

L-tryptophan + D-ribulose 5-phosphate = (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O

4.4.1.22

S-(hydroxymethyl)glutathione = glutathione + formaldehyde

4.5.1.3

5 entries

Substrate in Enzyme-catalyzed Reactions (151 results)

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1.1.1.1

formaldehyde + NADH + H+ = methanol + NAD+

285654, 285623, 285603, 688435, 739927, 712962

1.1.1.2

2 entries

1.1.1.202

formaldehyde + NADH + H+ = methanol + NAD+

740216

1.1.1.244

formaldehyde + NADH + H+ = methanol + NAD+

726329, 763722

1.1.1.263

formaldehyde + NADPH = methanol + NADP+

formaldehyde + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + NAD+ = S-formylmycothiol + NADH

288322, 288324, 288323

1.1.1.4

2 entries

1.1.1.71

formaldehyde + NADPH + H+ = methanol + NADP+

740200

1.1.1.72

formaldehyde + NADPH = methanol + NADP+

287287, 287283

1.1.1.B4

formaldehyde + NADH + H+ = methanol + NAD+

formaldehyde + 2 reduced cytochrome cL = methanol + 2 oxidizeded cytochrome cL

formaldehyde + N,N,N',N'-tetramethyl-p-phenylenediamine = methanol + ?

389953

1.1.99.20

formaldehyde + acceptor + H2O = formate + reduced acceptor

389904

1.1.99.37

formaldehyde + 4-(hydroxylamino)-N,N-dimethylaniline = methanol + N,N-dimethyl-4-nitrosoaniline

656101, 709849

1.14.13.82

3-(hydroxymethyl)-benzoate + NAD+ + H2O + formaldehyde = m-toluate + O2 + NADH + H+

639289

1.17.3.2

formaldehyde + H2O + O2 = ?

formaldehyde + NAD+ + H2O = formate + NADH

674270

1.2.1.24

formaldehyde + NAD+ + H2O = formate + NADH

674654

1.2.1.28

formaldehyde + NAD+ + H2O = formate + NADH + H+

formaldehyde + NADP+ + H2O = formate + NADPH + H+

formaldehyde + NAD+ + H2O = formate + NADH + H+

672682

1.2.1.88

formaldehyde + NAD+ + H2O = formate + NADH

formaldehyde + H2O + benzylviologen = formate + reduced benzylviologen

11936

1.2.99.8

formaldehyde + 2,6-dichlorophenolindophenol + H2O = formate + reduced 2,6-dichlorophenolindophenol

719397

1.5.1.5

formaldehyde + NADP+ = ?

392326

1.97.1.13

formaldehyde + H2O + oxidized methyl viologen = ?

674251

2.1.1.45

tetrahydrofolate + HCHO + dUMP = dihydrofolate + dTMP + H2O

formaldehyde + ? = ?

taurine + methanal = 2-sulfoacetaldehyde + methylamine

737516

3.5.99.12

dopamine + formaldehyde = norsalsolinol + H2O

774723

4.1.1.8

formaldehyde + formyl-CoA = glycolyl-CoA

768566

4.1.2.12

2-Oxo-3-methylbutanoate + formaldehyde = 2-Dehydropantoate

4901

4.1.2.19

Glycerone phosphate + formaldehyde = D-Erythrulose 1-phosphate

5049, 5071, 5066

4.1.2.2

Glycerone phosphate + formaldehyde = Erythrulose 1-phosphate

5077, 5076

4.1.2.4

formaldehyde + acetaldehyde = ?

pyruvate + formaldehyde = 4-hydroxy-2-oxobutanoic acid

768286

4.1.2.63

formaldehyde + formyl-CoA = glycolyl-CoA

774545

4.1.3.16

Pyruvate + formaldehyde = 2-Keto-4-hydroxybutyrate

5238

4.2.1.147

5,6,7,8-tetrahydromethanopterin + formaldehyde = 5,10-methylenetetrahydromethanopterin + H2O

725231, 727849, 758451

Product in Enzyme-catalyzed Reactions (612 results)

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1.1.1.1

methanol + NAD+ = formaldehyde + NADH + H+

1.1.1.103

methanol + NAD+ = formaldehyde + NADH + H+

methanol + NAD+ = formaldehyde + NADH + H+

methanol + ferricytochrome c = formaldehyde + ferrocytochrome c + H+

1.1.2.B2

5 entries

1.1.3.13

methanol + O2 = formaldehyde + H2O2

484910, 484915, 484909, 484912, 484913, 484916, 484917, 484924, 484914, 484920, 484923, 484907, 484911, 484918, 484919, 484921, 484905, 484906, 484925, 484922, 484908, -

1.1.3.6

methanol + O2 = methanal + H2O2

287674

1.1.5.11

methanol + a quinone = formaldehyde + a quinol

1.1.5.2

methanol + phenazine methosulfate = formaldehyde + reduced phenazine methosulfate

1.1.5.5

3 entries

1.1.99.36

methanol + N,N-dimethyl-4-nitrosoaniline = formaldehyde + 4-(hydroxylamino)-N,N-dimethylaniline

1.1.99.37

methanol + N,N-dimethyl-4-nitrosoaniline = formaldehyde + 4-(hydroxylamino)-N,N-dimethylaniline

1.11.1.16

1,4-dimethoxybenzene + H2O2 = 1,4-benzoquinone + formaldehyde + H2O

1.11.1.19

alpha-methylstyrene + H2O2 + H+ = acetophenone + formaldehyde

1.11.1.21

methanol + H2O2 = formaldehyde + H2O

nitromethane + O2 = formaldehyde + HNO2

N6-methyladenine in DNA + 2-oxoglutarate + O2 = adenine in DNA + formaldehyde + succinate + CO2

1-methylthymine + 2-oxoglutarate + O2 = 1-methyl-5-(hydroxymethyl)uracil + thymine + formaldehyde + succinate + CO2

439135, -

1,1-dimethylhydrazine + NADPH + O2 = formaldehyde + CH3N2H3 + NADP+

methanesulfonate + FMNH2 + O2 = formaldehyde + FMN + sulfite + H2O

1.14.14.35

dimethyl sulfone + FMNH2 + O2 = methanesulfinate + formaldehyde + FMN + H2O

1.14.14.5

methanesulfonate + FMNH2 + O2 = formaldehyde + FMN + sulfite + H2O

cyclo(L-tyrosyl-L-phenylalanyl-4-OMe) + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = cyclo(L-tyrosyl-L-tyrosyl) + formaldehyde + 2 oxidized ferredoxin [iron-sulfur] cluster + 2 H2O

formate + NADH = methanal + NAD+

glyoxylic acid + O2 + 2 H+ = CO2 + formaldehyde + H2O2

1.2.98.1

formate + methanol = formaldehyde

1.4.1.28

methylamin + NAD+ + H2O = formaldehyde + NH3 + NADH + H+

1.4.3.21

2 entries

1.4.3.4

methylamine + H2O + O2 = formaldehyde + NH3 + H2O2

1.4.9.1

11 entries

1.4.9.2

methylamine + acceptor + H2O = formaldehyde + NH3 + reduced acceptor

1.5.3.1

17 entries

1.5.3.10

N,N-dimethylglycine + H2O + O2 = sarcosine + formaldehyde + H2O2

394961, 394957, -

D-glyceraldehyde 3-phosphate + glycerone = D-xylulose 5-phosphate + formaldehyde

N,N-Dimethyl1-naphthylamine N-oxide = N-Methylaniline + formaldehyde

4.1.2.32

Trimethylamine N-oxide = Dimethylamine + formaldehyde

5133, 5134, 5136, 5137, 653047, 5135, -

4.1.2.43

D-arabino-hex-3-ulose 6-phosphate = D-ribulose 5-phosphate + formaldehyde

4.1.2.48

L-serine = glycine + formaldehyde

4.1.3.16

2-Keto-4-hydroxybutyrate = Pyruvate + formaldehyde

L-tyrosine + D-ribulose 5-phosphate = (2S)-3-(4-hydroxyphenyl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O

4.1.99.25

L-tryptophan + D-ribulose 5-phosphate = (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O

4.4.1.11

L-selenodjenkolate = pyruvate + NH3 + H2Se + formaldehyde

34525

4.4.1.22

S-(hydroxymethyl)glutathione = glutathione + formaldehyde

4.5.1.3

11 entries

Activator in Enzyme-catalyzed Reactions (5 results)

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1.1.1.284

in the presence of NAD+ and initial absence of NADH, ADH3-mediated S-nitrosoglutathione reduction is triggered by the presence of formaldehyde

maximal activity at 0.3 mM

392313

4.1.2.43

expression of the HPS coding hxlAB operon is induced by the presence of formaldehyde

694212

5.3.1.27

concomitant induction of 3-hexulose 6-phosphate synthase and 6-phospho-3-hexuloisomerase by formaldehyde

687363

Inhibitor in Enzyme-catalyzed Reactions (49 results)

484914, 484915, 724083

1.11.1.6

non-competitive inhibition

inhibits at 20% v/v

79.8% residual activity at 0.1 M

substrate inhibition

25% inhibition at 10 mM

30 mM

about 50% inhibition at 20 mM

decreases activity at levels up to 3fold higher than the maximally allowed workplace concentration, no decrease at the maximally allowed level

46% inactivation at 10 mM in presence of NaCNBH3

glyoxylate protects

20% (v/v), 2 h incubation, 81% loss of activity

725749

3.1.1.20

51.5% inhibition at 20% after 60 min at 30°C

709504

3.1.1.3

complete inhibition at 10% (v/v)

691764

3.1.25.1

total inhibition if 4.4 methylations per molecule are present

enzyme dimers in the presence of CO2 or formaldehyde form mutual, methylene-bridged cross-links between Lys158 and Cys245 residues

57% inhibition at 160 mM

1 mM, 53% inhibition

loss of 27-13% activity at 15-50% v/v after 24 h, loss of 46-47% activity after 1 h

3D Structure of Enzyme-Ligand-Complex (PDB) (137 results)

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (26 results)

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1.1.1.1

1.28

pH 7.0, 30°C

739927

1.1.1.202

1.6

pH 7.0, 37°C

0.267

pH 7.5, 30°C

67.5

enzyme ALDH-2

348694

1.2.1.4

0.33

pH 8.4, 28°C, cosubstrate NADP+

0.046

in 50 mM Tris-HCl (pH 7.5), at 25°C

688414

1.2.7.5

950

pH 8.4, 85°C, benzyl viologen as electron acceptor

950

with benzyl viologen as cosubstrate, at 85°C

K_M Value (128 results)

1.6

1° Adh

286197

1.1.1.202

16.1

pH 7.0, 37°C

9.6

pH 7.0, 20°C

161.5

0.00212

1.9

in 50 mM Tris-HCl (pH 7.5), at 25°C

688414

1.2.1.8

3.8

pH 7.7, coenzyme NAD+

656550

1.2.1.88

0.76

isoform A

392065

1.2.2.B1

0.143

20°C, pH 7.4

0.79

at pH 8.4 and 60Â°C

1.71

at pH 7.4 and 37°C

0.2

30°C, pH 8.0

725231

K_i Value (2 results)

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1.11.1.6

0.55

non-competitive inhibition

439788

1.2.1.3

348679

References & Links

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Show Reference (493 entries)

Links to other databases for formaldehyde

Ligand formaldehyde

Basic Ligand Information

Related pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (23 results)

In Vivo Product in Enzyme-catalyzed Reactions (235 results)

Substrate in Enzyme-catalyzed Reactions (151 results)

Product in Enzyme-catalyzed Reactions (612 results)

Activator in Enzyme-catalyzed Reactions (5 results)

Inhibitor in Enzyme-catalyzed Reactions (49 results)

3D Structure of Enzyme-Ligand-Complex (PDB) (137 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (26 results)

KM Value (128 results)

Ki Value (2 results)

References & Links

Literature References (493)

Links to other databases for formaldehyde

k_cat Value (Turnover Number) (26 results)

K_M Value (128 results)

K_i Value (2 results)