Ligand butan-1-ol

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Basic Ligand Information

Molecular Structure
Picture of butan-1-ol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C4H10O
butan-1-ol
LRHPLDYGYMQRHN-UHFFFAOYSA-N
Synonyms:
1-butanol, 1-butyl alcohol, 3-methylpropanol, butanol, Butanol-1, Butyl alcohol, n-butanol, n-Butyl alcohol

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1-butanol + NAD+ = butanal + NADH + H+
show the reaction diagram
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1-butyl alcohol + NAD+ = 1-butanal + NADH + H+
show the reaction diagram
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1-butanol + NAD(P)+ = butanal + NAD(P)H + H+
show the reaction diagram
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butanol + 2 cytochrome c = butyraldehyde + 2 reduced cytochrome c
show the reaction diagram
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butan-1-ol + ferricytochrome c = butanal + ferrocytochrome c + H+
show the reaction diagram
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butan-1-ol + a quinone = butanal + a quinol
show the reaction diagram
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1-butanol + acceptor = butanal + reduced acceptor
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
butane + NADH + H+ + O2 = butan-1-ol + NAD+ + H2O
show the reaction diagram
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-

Substrate in Enzyme-catalyzed Reactions (119 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
n-butanol + NAD+ = butanal + NADH + H+
show the reaction diagram
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butyl alcohol + NAD+ = butanal + NADH + H+
show the reaction diagram
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n-butanol + NAD+ + H2O = n-butanal + NADH
show the reaction diagram
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butanol + NADP+ = butyraldehyde + NADPH
show the reaction diagram
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1-butanol + NAD+ = butanal + NADH
show the reaction diagram
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butanol + glutathione + NAD+ = ?
show the reaction diagram
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1-butanol + NAD+ = n-butanal + NADH
show the reaction diagram
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1-butanol + NAD+ = butanal + NADH + H+
show the reaction diagram
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n-butanol + NAD+ = n-butanal + NADH
show the reaction diagram
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1-butanol + NAD+ = butanal + NADH + H+
show the reaction diagram
-
1-butanol + NAD+ = butanal + NADH
show the reaction diagram
-
butanol + 2 cytochrome c = butyraldehyde + 2 reduced cytochrome c
show the reaction diagram
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butan-1-ol + ferricytochrome c = butanal + ferrocytochrome c + H+
show the reaction diagram
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butanol + N,N,N',N'-tetramethyl-4-phenylenediamine = butyraldehyde + reduced N,N,N',N'-tetramethyl-4-phenylenediamine
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1-butanol + acceptor = butanal + reduced acceptor
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1-butanol + O2 = n-butanal + H2O2
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butan-1-ol + a quinone = butanal + a quinol
show the reaction diagram
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1-butanol + acceptor = n-butanal + reduced acceptor
show the reaction diagram
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butanol + O2 = ?
show the reaction diagram
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n-butanol + NAD+ + H2O = ? + NADH
show the reaction diagram
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1-butanol + acceptor = butanal + reduced acceptor
show the reaction diagram
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palmitoyl-CoA + butanol = butyl palmitate + CoA
show the reaction diagram
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UDPglucose + butyl alcohol = UDP + butyl beta-D-glucoside
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sucrose + butan-1-ol = butyl alpha-D-glucopyranoside + D-fructose
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O-acetyl-L-homoserine + n-butanol = O-butyl-homoserine + acetic acid
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3'-phosphoadenylylsulfate + 1-butanol = adenosine 3',5'-bisphosphate + 1-butanoyl sulfate
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4-nitrophenyl sulfate + 1-butanol = 4-nitrophenol + butyl sulfate
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gallate + 1-butanol = 1-butyl gallate + H2O
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oleate + 1-butanol = 1-butyl oleate + H2O
show the reaction diagram
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starch + butanol = butylglucoside + alpha-D-glucose
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n-butanol + phenyl alpha-D-galactoside = ?
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N-acetyllactosamine + butanol = butyl beta-N-acetyllactosaminide + H2O
show the reaction diagram
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di-N-acetylchitobiose + 1-butanol = ?
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dextran + 1-butanol = 1-butyl alpha-isomaltoside + H2O
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beta-D-Gal-(1-3)-alpha-D-GalNAc-(1-O)-p-nitrophenyl + 1-butanol = beta-D-Gal-(1-3)-alpha-D-GalNAc-(1-O)-butyl + p-nitrophenol
show the reaction diagram
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(2E,6E)-farnesol + n-butanol = drimane-8,11-diol + drimenol + albicanol + 8-O-((2E,6E)-farnesyl)-drimane-8,11-diol + drimane-8,11-diol + farnesyl pentyl ether
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (89 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
n-butyraldehyde + NADPH = n-butanol + NADP+
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butyraldehyde + NADPH = butanol + NADP+
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butyraldehyde + NADH + H+ = butan-1-ol + NAD+
show the reaction diagram
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butanal + NADPH = butan-1-ol + NADPH + H+
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butanal + NAD(P)H + H+ = butanol + NAD(P)+
show the reaction diagram
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N-butyraldehyde + NADH = 1-butanol + NAD+
show the reaction diagram
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butyraldehyde + a quinol = 1-butanol + a quinone
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butyraldehyde + reduced 2,6-dichlorophenolindophenol = 1-butanol + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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n-butylboronic acid + NADPH + O2 = n-butanol + BO3- + NADP+ + H2O
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butane + NADH + H+ + O2 = butan-1-ol + NAD+ + H2O
show the reaction diagram
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butane + NAD(P)H + O2 = 1-butanol + 2-butanol + NAD(P)+ + H2O
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butane + NAD(P)H + H+ + O2 = 1-butanol + 2-butanol + NAD(P)+ + H2O
show the reaction diagram
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formaldehyde + H2O + butyraldehyde = formate + butanol
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butyl acetate + H2O = butanol + acetate
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butyl 4-hydroxybenzoate + H2O = butanol + 4-hydroxybenzoate
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butyl acetate + H2O = butanol + acetate
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butyryl palmitate + H2O = butanol + palmitate
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butylthiocholine + H2O = thiocholine + butanol
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butyl acetate = acetate + butanol
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n-butyl benzyl phthalate + H2O = 1,3-isobenzofurandione + n-butanol + benzyl alcohol
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pimeloyl-[acyl-carrier protein] butyl ester + H2O = pimeloyl-[acyl-carrier protein] + butanol
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butyl O-beta-galactoside + H2O = butanol + beta-D-galactose
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butyl-beta-D-xyloside = butanol + beta-D-xylose
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butyl glutarate + hydoxylamine = glutaramate + butanol
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4-hydroxybutylflavin + H2O = butanol + lumichrome
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Activator in Enzyme-catalyzed Reactions (27 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
marginally increases the refolding yield in the presence of Arg, and it is unable to replace Arg in promoting a high refolding yield
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5% v/v, 2.9fold activation
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2 mM
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increases the yield of alpha-cyclodextrin
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activates
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0.1 M, increases activity
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increases activity by 2fold at 60% v/v concentration
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inhibits below 100 mM and activates above 100 mM
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transphosphatidylation increases activity
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20% (v/v), 25°C, pH 8.5, 2 h, 1.3fold activation
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20 mM, activates due to transglycosylation activity with over 80% of p-nitrophenyl beta-D-glucopyranoside being converted to 1-butyl beta-D-glucopyranoside in the presence of Cbg1 and 100 mM 1-butanol
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1%, 1.5fold activation
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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
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maximal activation is induced by 80 mM 1-butanol (130%). The activation at 30'C becomes less with increasing temperature and at 75°C is only 10%. Alcohol modifies the protein microenvironment, leading to a more flexible enzyme structure, which is probably responsible for the enhanced enzymatic activity
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activation e.g. between 0.75-2.5%, v/v, depending on substrate
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isoform AC6 shows about 85% stimulation of activity with 100 mM 1-butanol, isoform AC7 shows about 110% stimulation of activity with 100 mM 1-butanol, isoform AC9 shows about 105% stimulation of activity with 100 mM 1-butanol
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activation, 2% v/v, acidic enzyme form, not neutral enzyme form
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Inhibitor in Enzyme-catalyzed Reactions (87 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1% residual activity at 50% (v/v)
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5% v/v: 0-50% loss of activity, depending on substrate, enzyme regains activity after removal of alcohol
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n-butyl alcohol
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substrate inhibition
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81.0% residual activity at 30% (v/v)
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IC50 of 1.4 vol%
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; substrate formaldehyde
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10% (v/v), 48% inhibition; 52% inhibition
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50% inactivation at 5%
-
10% v/v, less than 65% inhibition; less than 65% activity in the presence of 10% (v/v)
-
at concentrations greater than 5times Km
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inhibits below 100 mM and activates above 100 mM
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10% inhibition at 40% v/v; 17% inhibition at 40% v/v
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reversible noncompetitive
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plasma membrane
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10%, 80% inhibition
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40%, relative activity is decreased to 85%
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10% v/v, about 35% loss of activity
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inhibition above 50 mM
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complete inhibition at 20-30% v/v
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about 30% residual activity at 10% (v/v)
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Ki: 2.7 mM
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68.24% residual activity at 50% (v/v)
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inhibition of esterolytic activity
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competitive inhibitors with respect to methylamine and ethanolamine
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48% decreased activity at 5% (v/v); 5% v/v, 48% inhibition
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50% inhibition at 2% v/v, 80% at 8% v/v
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3D Structure of Enzyme-Ligand-Complex (PDB) (12 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (37 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
5.7
-
pH 7.5, 37°C, recombinant enzyme
0.137
-
in 0.1 M potassium phosphate, pH 7.4
52.3
-
using 2,6-dichlorophenolindophenol as cosubstrate, pH 6.5, temperature not specified in the publication
21.5
-
pH 7.5, 30°C
0.283
-
pH 7.5, 37°C

KM Value (87 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.00802
-
at pH 8.8 and 37°C
9
-
pH 7.5, 37°C, recombinant enzyme
63
-
in 0.1 M potassium phosphate, pH 7.4
84
-
-
1.1
-
-
840
-
pH and temperature not specified in the publication
10
-
pH 8.5, 30°C
0.007
-
at pH 8.0 and 25°C
91.4
-
pH 9.0, 30°C, assayed with N,N,N',N'-tetramethyl-4-phenylenediamine
0.0017
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at pH 7.0 and 30°C
0.36
-
using 2,6-dichlorophenolindophenol as cosubstrate, pH 6.5, temperature not specified in the publication
0.0025
-
pH 7.0, 45°C
10.6
-
-
0.007
-
-
0.0014
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+ p-nitroso-N,N-dimethylaniline
2.34
-
pH 7.5, 30°C
70
-
pH 7.2, 37°C, cosubstrate oleate

Ki Value (7 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.65
-
pH 7.0, 45°C
1.7
-
-
5.4
-
substrate formaldehyde
2.7
-
-
670
-
pH 7.5, 25°C

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
-999
-
IC50: 4.5% (v/v)

References & Links

Links to other databases for butan-1-ol

ChEBI
PubChem
ChEBI
PubChem