Ligand formaldehyde

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Basic Ligand Information

Molecular Structure
Picture of formaldehyde (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
CH2O
formaldehyde
WSFSSNUMVMOOMR-UHFFFAOYSA-N
Synonyms:
carbonmonoxide, CH2O, CHOH, formalin, HCHO, methanal

Show all pahtways known for Show all pathways known for formaldehyde

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
formaldehyde + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + NAD+ = S-formylmycothiol + NADH
show the reaction diagram
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formaldehyde + O2 = formic acid + H2O2
show the reaction diagram
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formaldehyde + CoA + NAD+ = formyl-CoA + NADH + H+
show the reaction diagram
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formaldehyde + NAD+ + H2O = formate + NADH
show the reaction diagram
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formaldehyde + ferricytochrome b559/569 complex = formate + ferrocytochrome b559/569 complex
show the reaction diagram
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formaldehyde + H2O + oxidized ferredoxin = formate + H+ + reduced ferredoxin
show the reaction diagram
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formaldehyde + H2O + oxidized ferredoxin = formate + H+ + reduced ferredoxin
show the reaction diagram
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D-xylulose 5-phosphate + formaldehyde = glyceraldehyde 3-phosphate + dihydroxyacetone
show the reaction diagram
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5,6,7,8-tetrahydromethanopterin + formaldehyde = 5,10-methylenetetrahydromethanopterin + H2O
show the reaction diagram
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5,6,7,8-tetrahydromethanopterin + formaldehyde = 5,10-methylenetetrahydromethanopterin + H2O
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (161 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
methanol + NAD+ = formaldehyde + NADH + H+
show the reaction diagram
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methanol + NAD(P)+ = formaldehyde + NAD(P)H + H+
show the reaction diagram
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methanol + 2 cytochrome c = formaldehyde + 2 reduced cytochrome c
show the reaction diagram
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-
methanol + ferricytochrome c551i = formaldehyde + ferrocytochrome c551i
show the reaction diagram
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-
methanol + O2 = formaldehyde + H2O2
show the reaction diagram
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-
methanol + N,N-dimethyl-4-nitrosoaniline = formaldehyde + 4-(hydroxylamino)-N,N-dimethylaniline
show the reaction diagram
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-
N6-methyladenine in DNA + 2-oxoglutarate + O2 = adenine in DNA + formaldehyde + succinate + CO2
show the reaction diagram
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dimethylamine + NADPH + H+ + O2 = methylamine + formaldehyde + NADP+ + H2O
show the reaction diagram
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1,1-dimethylhydrazine + NADPH + O2 = formaldehyde + CH3N2H3 + NADP+
show the reaction diagram
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methanesulfonate + FMNH2 + O2 = formaldehyde + FMN + sulfite + H2O
show the reaction diagram
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-
dimethyl sulfone + FMNH2 + O2 = methanesulfinate + formaldehyde + FMN + H2O
show the reaction diagram
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formate + methanol = formaldehyde
show the reaction diagram
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methylamine + H2O + O2 = formaldehyde + NH3 + H2O2
show the reaction diagram
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N,N-dimethylglycine + H2O + O2 = sarcosine + formaldehyde + H2O2
show the reaction diagram
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epsilon-N-methyl groups in protein-bound methyllysine residues + O2 + H2O = demethylated lysine residues + formaldehyde + H2O2
show the reaction diagram
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N-methyl-L-glutamate + acceptor + H2O = L-glutamate + formaldehyde + reduced acceptor
show the reaction diagram
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methanethiol + O2 + H2O = formaldehyde + H2S + H2O2
show the reaction diagram
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Trimethylamine N-oxide = Dimethylamine + formaldehyde
show the reaction diagram
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D-arabino-hex-3-ulose 6-phosphate = D-ribulose 5-phosphate + formaldehyde
show the reaction diagram
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L-tyrosine + D-ribulose 5-phosphate = (2S)-3-(4-hydroxyphenyl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
show the reaction diagram
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L-tryptophan + D-ribulose 5-phosphate = (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
show the reaction diagram
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S-(hydroxymethyl)glutathione = glutathione + formaldehyde
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (118 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
formaldehyde + NADH + H+ = methanol + NAD+
show the reaction diagram
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formaldehyde + NADH + H+ = methanol + NAD+
show the reaction diagram
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formaldehyde + NADH + H+ = methanol + NAD+
show the reaction diagram
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formaldehyde + NADPH = methanol + NADP+
show the reaction diagram
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formaldehyde + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + NAD+ = S-formylmycothiol + NADH
show the reaction diagram
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formaldehyde + NADPH + H+ = methanol + NADP+
show the reaction diagram
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formaldehyde + NADPH = methanol + NADP+
show the reaction diagram
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formaldehyde + NADH + H+ = methanol + NAD+
show the reaction diagram
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formaldehyde + N,N,N',N'-tetramethyl-p-phenylenediamine = methanol + ?
show the reaction diagram
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formaldehyde + acceptor + H2O = formate + reduced acceptor
show the reaction diagram
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formaldehyde + 4-(hydroxylamino)-N,N-dimethylaniline = methanol + N,N-dimethyl-4-nitrosoaniline
show the reaction diagram
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formaldehyde + NAD+ + H2O = formate + NADH
show the reaction diagram
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formaldehyde + NAD+ + H2O = formate + NADH
show the reaction diagram
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formaldehyde + NAD+ + H2O = formate + NADH + H+
show the reaction diagram
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formaldehyde + NADP+ + H2O = formate + NADPH + H+
show the reaction diagram
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formaldehyde + NADP+ + H2O = formate + NADPH + H+
show the reaction diagram
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formaldehyde + NAD+ + H2O = formate + NADH + H+
show the reaction diagram
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formaldehyde + NAD+ + H2O = formate + NADH
show the reaction diagram
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formaldehyde + H2O + benzylviologen = formate + reduced benzylviologen
show the reaction diagram
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formaldehyde + 2,6-dichlorophenolindophenol + H2O = formate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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formaldehyde + NADP+ = ?
show the reaction diagram
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formaldehyde + ? = ?
show the reaction diagram
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taurine + methanal = 2-sulfoacetaldehyde + methylamine
show the reaction diagram
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2-Oxo-3-methylbutanoate + formaldehyde = 2-Dehydropantoate
show the reaction diagram
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Glycerone phosphate + formaldehyde = D-Erythrulose 1-phosphate
show the reaction diagram
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Glycerone phosphate + formaldehyde = Erythrulose 1-phosphate
show the reaction diagram
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Pyruvate + formaldehyde = 2-Keto-4-hydroxybutyrate
show the reaction diagram
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5,6,7,8-tetrahydromethanopterin + formaldehyde = 5,10-methylenetetrahydromethanopterin + H2O
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (405 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
methanol + NAD+ = formaldehyde + NADH + H+
show the reaction diagram
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methanol + NAD+ = formaldehyde + NADH + H+
show the reaction diagram
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methanol + NADP+ = formaldehyde + NADPH + H+
show the reaction diagram
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methanol + NAD+ = formaldehyde + NADH + H+
show the reaction diagram
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methanol + NAD(P)+ = formaldehyde + NAD(P)H + H+
show the reaction diagram
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methanol + 2 cytochrome c = formaldehyde + 2 reduced cytochrome c
show the reaction diagram
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methanol + ferricytochrome c = formaldehyde + ferrocytochrome c + H+
show the reaction diagram
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methanol + O2 = methanal + H2O2
show the reaction diagram
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methanol + a quinone = formaldehyde + a quinol
show the reaction diagram
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methanol + phenazine methosulfate = formaldehyde + reduced phenazine methosulfate
show the reaction diagram
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methanol + N,N-dimethyl-4-nitrosoaniline = formaldehyde + 4-(hydroxylamino)-N,N-dimethylaniline
show the reaction diagram
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methanol + H2O2 = formaldehyde + H2O
show the reaction diagram
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nitromethane + O2 = formaldehyde + HNO2
show the reaction diagram
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N6-methyladenine in DNA + 2-oxoglutarate + O2 = adenine in DNA + formaldehyde + succinate + CO2
show the reaction diagram
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1-methylthymine + 2-oxoglutarate + O2 = 1-methyl-5-(hydroxymethyl)uracil + thymine + formaldehyde + succinate + CO2
show the reaction diagram
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1,1-dimethylhydrazine + NADPH + O2 = formaldehyde + CH3N2H3 + NADP+
show the reaction diagram
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methanesulfonate + FMNH2 + O2 = formaldehyde + FMN + sulfite + H2O
show the reaction diagram
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dimethyl sulfone + FMNH2 + O2 = methanesulfinate + formaldehyde + FMN + H2O
show the reaction diagram
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formate + NADH = methanal + NAD+
show the reaction diagram
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glyoxylic acid + O2 + 2 H+ = CO2 + formaldehyde + H2O2
show the reaction diagram
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formate + methanol = formaldehyde
show the reaction diagram
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methylamine + H2O + O2 = formaldehyde + NH3 + H2O2
show the reaction diagram
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methylamine + acceptor + H2O = formaldehyde + NH3 + reduced acceptor
show the reaction diagram
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N,N-dimethylglycine + H2O + O2 = sarcosine + formaldehyde + H2O2
show the reaction diagram
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methanethiol + O2 + H2O = formaldehyde + H2S + H2O2
show the reaction diagram
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N,N-Dimethyl1-naphthylamine N-oxide = N-Methylaniline + formaldehyde
show the reaction diagram
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Trimethylamine N-oxide = Dimethylamine + formaldehyde
show the reaction diagram
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D-arabino-hex-3-ulose 6-phosphate = D-ribulose 5-phosphate + formaldehyde
show the reaction diagram
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L-serine = glycine + formaldehyde
show the reaction diagram
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2-Keto-4-hydroxybutyrate = Pyruvate + formaldehyde
show the reaction diagram
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L-tyrosine + D-ribulose 5-phosphate = (2S)-3-(4-hydroxyphenyl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
show the reaction diagram
-
-
L-tryptophan + D-ribulose 5-phosphate = (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
show the reaction diagram
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L-selenodjenkolate = pyruvate + NH3 + H2Se + formaldehyde
show the reaction diagram
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S-(hydroxymethyl)glutathione = glutathione + formaldehyde
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
in the presence of NAD+ and initial absence of NADH, ADH3-mediated S-nitrosoglutathione reduction is triggered by the presence of formaldehyde
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maximal activity at 0.3 mM
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expression of the HPS coding hxlAB operon is induced by the presence of formaldehyde
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concomitant induction of 3-hexulose 6-phosphate synthase and 6-phospho-3-hexuloisomerase by formaldehyde
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Inhibitor in Enzyme-catalyzed Reactions (45 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
non-competitive inhibition
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inhibits at 20% v/v
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79.8% residual activity at 0.1 M
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substrate inhibition
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25% inhibition at 10 mM
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30 mM
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decreases activity at levels up to 3fold higher than the maximally allowed workplace concentration, no decrease at the maximally allowed level
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inactivation
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46% inactivation at 10 mM in presence of NaCNBH3
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glyoxylate protects
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20% (v/v), 2 h incubation, 81% loss of activity
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complete inhibition at 10% (v/v)
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total inhibition if 4.4 methylations per molecule are present
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57% inhibition at 160 mM
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1 mM, 53% inhibition

3D Structure of Enzyme-Ligand-Complex (PDB) (88 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (19 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
1.28
-
pH 7.0, 30C
1.6
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pH 7.0, 37C
0.267
-
-
32
-
pH 7.5, 30C
67.5
-
enzyme ALDH-2
0.33
-
pH 8.4, 28C, cosubstrate NADP+
0.046
-
in 50 mM Tris-HCl (pH 7.5), at 25C
950
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pH 8.4, 85C, benzyl viologen as electron acceptor
950
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with benzyl viologen as cosubstrate, at 85C

KM Value (117 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.6
-
1 Adh
16.1
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pH 7.0, 37C
9.6
-
-
3
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pH 7.0, 20C
161.5
-
-
0.00212
-
-
1.9
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in 50 mM Tris-HCl (pH 7.5), at 25C
3.8
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pH 7.7, coenzyme NAD+
0.76
-
isoform A
0.143
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20C, pH 7.4
0.35
-
-
0.79
-
-
31
-
-
0.2
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30C, pH 8.0

Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.55
-
non-competitive inhibition
6
-
-

References & Links