Ligand methanol

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Basic Ligand Information

Molecular Structure
Picture of methanol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
CH4O
methanol
OKKJLVBELUTLKV-UHFFFAOYSA-N
Synonyms:
CH3OH, methyl alcohol


Show all pahtways known for Show all BRENDA pathways known for methanol

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
methanol + NAD+ = formaldehyde + NADH + H+
show the reaction diagram
-
methanol + NAD(P)+ = formaldehyde + NAD(P)H + H+
show the reaction diagram
-
methanol + 2 cytochrome c = formaldehyde + 2 reduced cytochrome c
show the reaction diagram
-
methanol + ferricytochrome c551i = formaldehyde + ferrocytochrome c551i
show the reaction diagram
-
methanol + N,N-dimethyl-4-nitrosoaniline = formaldehyde + 4-(hydroxylamino)-N,N-dimethylaniline
show the reaction diagram
-
formate + methanol = formaldehyde
show the reaction diagram
-
anthraniloyl-CoA + methanol = CoA + O-methyl anthranilate
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (43 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
methyl gallate + H2O = gallic acid + methanol
show the reaction diagram
-
cocaine + ethanol = cocaethylene + methanol
show the reaction diagram
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polyneuridine aldehyde + H2O = 16-epivellosimine + CO2 + methanol
show the reaction diagram
-
-
pheophorbide a + H2O = pyropheophorbide a + methanol + CO2
show the reaction diagram
-
-
pimeloyl-[acyl-carrier protein] methyl ester + H2O = pimeloyl-[acyl-carrier protein] + methanol
show the reaction diagram
-
-
[phosphatase 2A protein]-leucine methyl ester + H2O = [phosphatase 2A protein]-leucine + methanol
show the reaction diagram
-
-
aclacinomycin T + H2O = 15-demethylaclacinomycin T + methanol
show the reaction diagram
-
-
diphthine methyl ester-[translation elongation factor 2] + H2O = diphthine-[translation elongation factor 2] + methanol
show the reaction diagram
-
-
2,4-dinitroanisole + H2O = methanol + 2,4-dinitrophenol
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (76 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
methanol + NAD+ = formaldehyde + NADH + H+
show the reaction diagram
-
methanol + NADP+ = formaldehyde + NADPH + H+
show the reaction diagram
-
methanol + NAD+ = formaldehyde + NADH + H+
show the reaction diagram
-
methanol + NAD(P)+ = formaldehyde + NAD(P)H + H+
show the reaction diagram
-
methanol + 2 cytochrome c = formaldehyde + 2 reduced cytochrome c
show the reaction diagram
-
methanol + ferricytochrome c = formaldehyde + ferrocytochrome c + H+
show the reaction diagram
-
methanol + O2 = methanal + H2O2
show the reaction diagram
-
methanol + a quinone = formaldehyde + a quinol
show the reaction diagram
-
methanol + phenazine methosulfate = formaldehyde + reduced phenazine methosulfate
show the reaction diagram
-
methanol + N,N-dimethyl-4-nitrosoaniline = formaldehyde + 4-(hydroxylamino)-N,N-dimethylaniline
show the reaction diagram
-
methanol + N,N-dimethyl-4-nitrosoaniline = formaldehyde + 4-(hydroxylamino)-N,N-dimethylaniline
show the reaction diagram
-
methanol + H2O2 = formaldehyde + H2O
show the reaction diagram
-
methanol + O2 = ?
show the reaction diagram
-
methanol + NADH + H+ + O2 = ? + H2O + NAD+
show the reaction diagram
formate + methanol = formaldehyde
show the reaction diagram
-
anthraniloyl-CoA + methanol = CoA + O-methyl anthranilate
show the reaction diagram
-
sucrose + methanol = glucose + methyl-beta-D-fructoside
show the reaction diagram
-
O-acetyl-L-homoserine + methanol = O-methyl-homoserine + acetic acid
show the reaction diagram
-
3'-phosphoadenylylsulfate + methanol = adenosine 3',5'-bisphosphate + methyl sulfate
show the reaction diagram
-
chlorophyll a + CH3OH + phytol = methylchlorophyllide + ?
show the reaction diagram
-
gallate + methanol = methyl gallate + H2O
show the reaction diagram
-
oleate + methanol = oleic acid methyl ester
show the reaction diagram
-
oleate + methanol = methyl oleate + H2O
show the reaction diagram
-
adenosine 5'-triphosphate + methanol = adenosine 5'-monophosphate-O-methyl ester + H2O + diphosphate
show the reaction diagram
-
p-nitrophenyl phosphate + methanol = p-nitrophenol + methylphosphate
show the reaction diagram
-
phosphatidylcholine + methanol = phosphatidylmethanol + choline
show the reaction diagram
-
starch + methanol = methylglucoside + alpha-D-glucose
show the reaction diagram
-
Galbeta(1-3)GalNAcbeta(1-4)(NeuAcalpha(2-3))Galbeta(1-4)Glcbeta(1-1)ceramide + methanol = ?
show the reaction diagram
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cellobiose + methanol = methyl-beta-D-glucopyranoside + beta-D-glucose
show the reaction diagram
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4-O-beta-D-mannopyranosyl-D-mannopyranose + methanol = ?
show the reaction diagram
-
4-methylumbelliferyl-alpha-L-iduronide + methanol = ?
show the reaction diagram
-
dextran + methanol = methyl alpha-isomaltoside + H2O
show the reaction diagram
-
beta-D-Gal-(1-3)-alpha-D-GalNAc-(1-O)-p-nitrophenyl + methanol = beta-D-Gal-(1-3)-alpha-D-GalNAc-(1-O)-methyl + p-nitrophenol
show the reaction diagram
-
N-benzoyl-L-tyrosine ethyl ester + methanol = N-benzoyl-L-tyrosine methyl ester + ethanol
show the reaction diagram
-
glutaramate + methanol = glutarate methyl ester + hydroxylamine
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (670 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
formaldehyde + NADH + H+ = methanol + NAD+
show the reaction diagram
-
-
formaldehyde + NADH + H+ = methanol + NAD+
show the reaction diagram
-
-
formaldehyde + NADH + H+ = methanol + NAD+
show the reaction diagram
-
-
formaldehyde + NADPH = methanol + NADP+
show the reaction diagram
-
formaldehyde + NADPH + H+ = methanol + NADP+
show the reaction diagram
-
-
formaldehyde + NADPH = methanol + NADP+
show the reaction diagram
-
-
formaldehyde + NADH + H+ = methanol + NAD+
show the reaction diagram
-
-
formaldehyde + N,N,N',N'-tetramethyl-p-phenylenediamine = methanol + ?
show the reaction diagram
-
-
formaldehyde + 4-(hydroxylamino)-N,N-dimethylaniline = methanol + N,N-dimethyl-4-nitrosoaniline
show the reaction diagram
-
-
methane + NADH + H+ + O2 = methanol + NAD+ + H2O
show the reaction diagram
-
-
methylbutyrate + H2O = methanol + butanoate
show the reaction diagram
-
-
S-methyl thiobutanoate + H2O = methanol + thiobutanoate
show the reaction diagram
-
-
methyl butyrate + H2O = methanol + butanoate
show the reaction diagram
-
-
deacetyl-7-aminocephalosporanic acid + methyl acetate = 7-aminocephalosporanic acid + methanol
show the reaction diagram
-
oxaloacetate 4-methyl ester = oxaloacetate + methanol
show the reaction diagram
-
methyl butyrate + H2O = methanol + butyrate
show the reaction diagram
-
N5-dinitrophenyl-L-ornithine methyl ester + H2O = N5-dinitrophenyl-L-ornithine + methanol
show the reaction diagram
-
methyl acetate + H2O = methanol + acetate
show the reaction diagram
-
-
dimethylphthalate + H2O = methylphthalate + methanol
show the reaction diagram
-
-
cocaine + ethanol = cocaethylene + methanol
show the reaction diagram
-
methylthiocholine + H2O = thiocholine + methanol
show the reaction diagram
-
-
pheophorbide a + H2O = pyropheophorbide a + methanol + CO2
show the reaction diagram
-
-
aclacinomycin T + H2O = 15-demethylaclacinomycin T + methanol
show the reaction diagram
-
-
diphthine methyl ester-[translation elongation factor 2] + H2O = diphthine-[translation elongation factor 2] + methanol
show the reaction diagram
-
-
Methyl-phosphate + H2O = Methanol + phosphate
show the reaction diagram
-
-
methylphosphate + H2O = methanol + phosphate
show the reaction diagram
-
-
dimethyl phosphate + H2O = methanol + methyl phosphate
show the reaction diagram
-
-
Monomethyl sulfate + H2O = Methanol + sulfate
show the reaction diagram
-
methyl alpha-D-glucopyranoside + H2O = methanol + alpha-D-glucopyranose
show the reaction diagram
-
-
methyl-beta-D-glucoside + H2O = methanol + beta-D-glucose
show the reaction diagram
-
-
methyl alpha-D-galactoside + H2O = methanol + D-galactose
show the reaction diagram
-
-
methyl-alpha-D-glucoside + H2O = methanol + alpha-D-glucose
show the reaction diagram
-
-
methyl beta-D-glucoside + H2O = methanol + D-glucose
show the reaction diagram
-
-
methyl alpha-L-fucopyranoside + H2O = methanol + alpha-L-fucose
show the reaction diagram
-
-
methyl-beta-N-acetyl-glucosaminide + H2O = methanol + beta-N-acetyl-glucosamine
show the reaction diagram
-
-
beta-methylglucoside + H2O = methanol + beta-D-glucose
show the reaction diagram
-
methyl beta-D-galactoside = methanol + D-galactose
show the reaction diagram
-
-
methyl beta-D-galactoside = methanol + D-galactose
show the reaction diagram
-
-
methyl beta-D-galactoside = methanol + beta-D-galactose
show the reaction diagram
-
-
methyl beta-D-glucopyranoside + H2O = methanol + beta-D-glucose
show the reaction diagram
-
-
2,4-dinitroanisole + H2O = methanol + 2,4-dinitrophenol
show the reaction diagram
-
-
ubiquitin glycine methyl ester + H2O = ubiquitin + methanol
show the reaction diagram
-
-
L-Asp beta-methyl ester + H2O = L-Asp + methanol
show the reaction diagram
-
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N-acetyl-L-Tyr methyl ester + H2O = N-acetyl-L-Tyr + methanol
show the reaction diagram
-
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Nalpha-toluenesulfonyl-L-arginine methyl ester + H2O = Nalpha-toluenesulfonyl-L-arginine + methanol
show the reaction diagram
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tosyl arginine methyl ester + H2O = tosyl-Arg + methanol
show the reaction diagram
-
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Benzoyl-L-Arg methyl ester + H2O = Benzoyl-L-Arg + methanol
show the reaction diagram
-
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Tosyl-Arg methyl ester + H2O = Tosyl-Arg + methanol
show the reaction diagram
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Tosyl-L-Arg methyl ester + H2O = Tosyl-L-Arg + methanol
show the reaction diagram
-
-
p-toluenesulfonyl-L-arginine methyl ester + H2O = p-toluenesulfonyl-L-arginine + methyl alcohol
show the reaction diagram
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Gly-Leu-Gly-Gln-Met methyl ester + H2O = Gly-Leu-Gly-Gln-Met + CH3OH
show the reaction diagram
-
hippuryl methyl ester + H2O = hippuric acid + methanol
show the reaction diagram
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-
N-tosyl-L-Arg methyl ester + H2O = N-tosyl-L-Arg + methanol
show the reaction diagram
-
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N-tosyl-L-Arg methyl ester + H2O = N-tosyl-Arg + methanol
show the reaction diagram
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Z-Phe-Arg-OMe + SerNH2 = Z-Phe-Arg-Ser-NH2 + methanol
show the reaction diagram
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methyl nicotinate + H2O = nicotinate + methanol
show the reaction diagram
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methyl-delta-aminovalerate + H2O = 5-aminopentanoate + methanol
show the reaction diagram
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oleoyl methyl ester + H2O = oleic acid + methanol
show the reaction diagram
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5,10-methenyltetrahydrofolate + H2O = 10-formyltetrahydrofolate + H+ + methanol
show the reaction diagram
-
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chloromethane + H2O = methanol + chloride
show the reaction diagram
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atratone + H2O = 4-(ethylamino)-2-hydroxy-6-(isopropylamino)-1,3,5-triazine + methanol
show the reaction diagram
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-

Activator in Enzyme-catalyzed Reactions (83 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
can replace an unidentified activating factor
-
activation is reversible and inversely related to the temperature
-
increases the activity of the oxidized truncated enzyme form, optimal concentration 8%
-
induces enzyme expression at 3%
-
activates 1.15fold at 10%
-
the enzyme activity is the highest when methanol is used as solvent, optimal at 6%
-
10% v/v, 1.6fold activation
-
12fold activity increase by 30% methanol
-
addition of methanol to in vitro assays has a stimulatory effect on activity at concentrations up to 25%
-
addition of methanol to in vitro assays has a stimulatory effect on activity at concentrations up to 25%
-
dietary methanol exposure dramatically increases enzyme activity
-
bacterial luciferase luminescence intensity slightly increases during the initial stage of the methanol injection
-
reaction with meta-chloroperbenzoic acid in the presence of methanol (3% or ca. 1 M after mixing) at pH 7.4 and 25°C results in the accumulation of a considerable fraction of the P450cam as the putative Cpd II species
-
reaction rate 111%
-
increases maximal reaction rate
-
slightly stimulating
-
activity is increased about 6fold in the presence of 5% methanol (v/v)
-
used in the assay as activating compound in concentration of 0.5% for 96 h
-
the catalytic efficiency in 30% (v/v) methanol is 1.15fold than that of in the aqueous phase
-
activates
-
MtaB plus methanol positively affect the catalytic efficiency of MtaA. activation of MtaA by MtaB is methanol-dependent. Methylation of cob(I)inamide with methanol is dependent on imidazole but not on the demethylation of methylcob(III)inamide with coenzyme M. The demethylation reaction is even inhibited by imidazole
-
activation, arachidonoyl-CoA as substrate
-
20% v/v, 17% activation
-
53.26% increased yield of S-adenosyl-L-methionine at 1.0% methanol
-
activates
-
30%, 2.3fold stimulation
-
maximal stimulation of GPSI by 20% v/v
-
at 1% v/v
-
methanol increases the enzyme activity to 111%
-
10% (v/v): 137% activity compared to no addition
-
activates enzyme form A and B
-
enzyme activity increases to 104.4% in the presence of 10% (v/v) methanol
-
about 125% activity at 25% (v/v)
1%, 1.4fold activation
-
linear increase in enzyme-catalyzed cleavage of p-nitrophenyl alpha-L-fucoside and fucosyl fluoride
-
aqueous methanol system, up to 40% methanol, increases transglycosylation
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the liberation of aglycone from aryl beta-D-glucosides is stimulated by alcohols in a manner suggesting specific interaction between alcohol and enzyme
-
alcohol modifies the protein microenvironment, leading to a more flexible enzyme structure, which is probably responsible for the enhanced enzymatic activity
-
a methanol based deblocking solution preserves enzymatic activity, provides conditions compatible with sequencing and enhances deblocking of electroblotted samples
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25% v/v, 4fold increase of the activity, methoxycarbonyl-D-Nle-Gly-Arg-p-nitroanilide as substrate, rFIXa, alcohols modify the conformation of FIXa rendering the active-site cleft more easily accessible to tripeptide substrates with a hydrophobic residue in the P3-position
-
uncompetitive activation
-
optimal activation e.g. between 5-15%, v/v, depending on substrate
-
slight activation at concentration of 4 M
-
stimulation by aliphatic alcohols in a decreasing order of effectiveness: ethylene glycol > 2-propanol > ethanol > glycerol > methanol > 1-propanol
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strong stimulation
-
active at 15-30% v/v methanol with an optimal concentration of 25%
-

Inhibitor in Enzyme-catalyzed Reactions (166 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
50% (v/v), 30% loss of activity
-
40% (v/v), 50% activity
-
20% (v/v), 30% loss of activity
-
14% residual activity at 10% (v/v)
-
10% v/v: 25-75% loss of activity, 5% v/v, 50-95% loss of activity, depending on substrate, enzyme regains activity after removal of alcohol
-
75% inhibition in buffer without NaCl, 81% inhibition in buffer with 600 mM NaCl
-
substrate inhibition
-
the native enzyme shows less than 5% residual activity in the presence of methanol
-
in vitro inhibitor
-
85.0% residual activity at 70% (v/v)
-
complete inhibition at 50% v/v
-
inhibits at 20% v/v
-
40% inhibition at 30% concentration as co-solvent
-
partially affects (10-20%) activity of the active recombinant enzyme; partially affects (10-20%) activity of the active recombinant enzyme; partially affects (10-20%) activity of the active recombinant enzyme; partially affects (10-20%) activity of the active recombinant enzyme; partially affects (10-20%) activity of the active recombinant enzyme; partially affects (10-20%) activity of the active recombinant enzymes
-
bacterial luciferase luminescence intensity decreases to the steady state depending on the methanol concentration
-
10%, v/v, complete inhibition of hydroxylation
-
complete inhibition at 40% (v/v)
-
complete inhibition at 2% (v/v)
-
1 M, 62% inhibition
-
54% residual activity after 30 min incubation at 30% (v/v)
-
at nonsaturating concentrations of phenylethanolamine, methanol inhibits in a competitive fashion. With respect to S-adenosyl-L-methionine inhibition by methanol is noncompetitive
-
oleoyl-CoA as substrate
-
10% (v/v), 30% inhibition; 70% inhibition
-
about 45.2% decreased enzyme activity, 10%
-
5 mM, 36% loss of activity
-
2.4% methanol depresses methionine adenosyltransferase specific activity, this effect is not observed with 0.8% methanol
-
10% v/v, weak
-
48% residual activity in the presence of 90% (v/v) methanol, after 60 min at 70°C
-
above 20% v/v
-
inhibitory above 0.14 mM
-
91% inhibition at 10% (vol/vol)
-
80-90% inhibition
-
48% residual activity in the presence of 90% (v/v) methanol, after 60 min at 70°C
-
20% (v/v), 2 h, 20°C, 44% loss of activity
-
excess amounts inhibit
-
68% residual activity at 1 mM
-
moderate inhibition at 5 mM
-
10% v/v, about 5% loss of activity
-
91.6% residual activity at 10% (v/v)
-
inhibition above 50 mM
-
99% inhibition at 10%
-
inhibits 15% and 50% at 5% and 10% v/v, respectively
-
5%, 26.5% inhibition of activity with carboxymethyl cellulose, 13.5% inhibition of xylanase activity, fusion enzyme (EG-M-Xyn) of endoglucanase (cellulase) from Teleogryllus emma and xylanase from Thermomyces lanuginosus
-
20%, 22.4% loss of activity
-
10% (v/v), about% inhibition
-
methanol-H2O at 1:2 (v/v) leads to a loss of activity of about only 20%. The enzyme is completely inactivated by methanol-H2O at above 1:1 (v/v)
-
hydration of trans-stilbene oxide
-
reduces the activity by 86% at 3.75% v/v
-
Ki: 860 mM
-
inactivation only above 30%
-
inhibition of esterolytic activity
-
incubation in 20% (v/v) methanol (10-20 h, 4°C) results in partial decomposition of the high molecular weight PSP-GroEL complex with precipitation of denatured chaperonin and a small (no more than 10%) loss of PSP activity
-
about 15% as effective as n-butanol
-
MD calculations, discussion of effects
-
the enzyme is relatively active in 5% (v/v) methanol with 60% of the enzyme activity remaining
-
enzyme activity is gradually lost in the presence of increasing concentrations of methanol and completely lost at 65%
-
94% of maximum activity when assayed in 40% (v/v) methanol
-
45% residual activity at 8% (v/v) methanol
-
2% (v/v), 19.2% inhibition
moderate, nonspecific
-
inactivates the EAL holoenzyme
-
10%, 26% inhibition
-

Metals and Ions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
15% v/v, 1.4fold activation. 30% v/v, 1.7fold activation
-
activates by 54% at 5% v/v
-

3D Structure of Enzyme-Ligand-Complex (PDB) (47 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (23 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
76
-
pH 7.5, 70°C, wild-type enzyme
18.5
-
pH 7.5, 30°C
0.0833
-
pH 7.5, 37°C

KM Value (64 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.56
-
pH 9.0, 30°C, assayed with N,N,N',N'-tetramethyl-4-phenylenediamine
0.00015
-
pH 7.5, 70°C, wild-type enzyme
83
-
peroxidase activity
0.04
-
+ p-nitroso-N,N-dimethylaniline
40
-
beta subunit MtaB
4.05
-
pH 7.5, 30°C
2300
-
-
1300
-
pH 7.2, 37°C, cosubstrate oleate, value above
5000
-
with substrate, acyl donor: glutaramate

Ki Value (5 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
6500
-
-
480
-
-
71.6
-
-
0.08416
-
-
430
-
pH 7.5, 25°C

References & Links