Ligand acetone

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Basic Ligand Information

Molecular Structure
Picture of acetone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C3H6O
acetone
CSCPPACGZOOCGX-UHFFFAOYSA-N
Synonyms:
2-oxopropane, 2-Propanone, aceton, dimethylketone, isopropanal, Ketone, methyl ketone, propan-2-one, propanone
Pathway Source
Pathways
BRENDA
propanol degradation
KEGG
Biosynthesis of secondary metabolites, Cutin, suberine and wax biosynthesis, Propanoate metabolism, Synthesis and degradation of ketone bodies
MetaCyc
acetone degradation I (to methylglyoxal), acetone degradation II (to acetoacetate), acetone degradation III (to propane-1,2-diol), atrazine degradation II, cuticular wax biosynthesis more


Show all pahtways known for Show all BRENDA pathways known for acetone

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetone + NAD(P)H + H+ = propan-2-ol + NAD(P)+
show the reaction diagram
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acetone + NADPH + H+ + O2 = methyl acetate + NADP+ + H2O
show the reaction diagram
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cyanide + acetone = 2-hydroxy-2-methylpropanenitrile
show the reaction diagram
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acetone + CO2 + ATP + H2O = acetoacetate + AMP + phosphate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (36 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-propanol + NADP+ = acetone + NADPH
show the reaction diagram
-
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2-propanol + NAD(P)+ = propan-2-one + NAD(P)H + H+
show the reaction diagram
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propan-2-ol + NADP+ = acetone + NADPH + H+
show the reaction diagram
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isopropanol + O2 = 2-propanone + H2O2
show the reaction diagram
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2-propanol + O2 = propan-2-one + H2O2
show the reaction diagram
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(+)-columbianetin + [reduced NADPH-hemoprotein reductase] + O2 = angelicin + acetone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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acetoacetate + H+ = acetone + CO2
show the reaction diagram
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2-hydroxy-2-methylpropanenitrile = cyanide + acetone
show the reaction diagram
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(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O = (-)-geosmin + acetone
show the reaction diagram
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-

Substrate in Enzyme-catalyzed Reactions (32 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetone + NADH + H+ = ? + NAD+
show the reaction diagram
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acetone + NADPH + H+ = propan-2-ol + NADP+
show the reaction diagram
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propan-2-one + NADH + H+ = propan-2-ol + NAD+
show the reaction diagram
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acetone + NADPH + H+ = propan-2-ol + NADP+
show the reaction diagram
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acetone + NADPH + H+ + O2 = methyl acetate + NADP+ + H2O
show the reaction diagram
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pyruvate oxime + acetone = pyruvate + acetoxime
show the reaction diagram
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L-glyceraldehyde 3-phosphate + propanone = 1,3-dideoxy-6-O-phosphono-L-threo-hex-2-ulose
show the reaction diagram
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cyanide + acetone = 2-hydroxy-2-methylpropanenitrile
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (152 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
propan-2-ol + NADP+ = acetone + NADPH
show the reaction diagram
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2-propanol + NADP+ = propanone + NADPH + H+
show the reaction diagram
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isopropanol + NAD+ = isopropanal + NADH + H+
show the reaction diagram
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2-propanol + NAD+ = acetone + NADH
show the reaction diagram
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2-propanol + NAD+ = acetone + NADH + H+
show the reaction diagram
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2-propanol + NAD+ = acetone + NADH + H+
show the reaction diagram
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2-propanol + NAD+ = acetone + NADH
show the reaction diagram
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2-propanol + NAD+ = 2-propanone + NADH + H+
show the reaction diagram
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2-propanol + NAD+ = acetone + NADH
show the reaction diagram
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propan-2-ol + NAD+ = propan-2-one + NADH + H+
show the reaction diagram
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isopropanol + NAD+ = isopropanal + NADH + H+
show the reaction diagram
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2-propanol + acceptor = 2-propanone + reduced acceptor
show the reaction diagram
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2-propanol + O2 = acetone + H2O2
show the reaction diagram
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propan-2-ol + a quinone = acetone + a quinol
show the reaction diagram
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2-propanol + pyrroloquinoline quinone = acetone + pyrroloquinoline quinol
show the reaction diagram
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2-propanol + acceptor = acetone + reduced acceptor
show the reaction diagram
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2-propanol + N,N-dimethyl-4-nitrosoaniline = acetone + 4-(hydroxylamino)-N,N-dimethylaniline
show the reaction diagram
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2-(propan-2-yloxy)propane + H2O2 = propan-2-one + propan-2-ol + H2O
show the reaction diagram
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(+)-columbianetin + [reduced NADPH-hemoprotein reductase] + O2 = angelicin + acetone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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2-bromopropane + duroquinol + O2 = 2-bromo-1-propanol + acetone + duroquinone + H2O
show the reaction diagram
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methyl vinyl ketone + NAD(P)H = dimethylketone + NAD(P)+
show the reaction diagram
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methylacetoin + D-ribose 5-phosphate = acetone + 1-deoxy-D-altro-heptulose 7-phosphate
show the reaction diagram
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4-phenyl-2-butanone + isopropylamine = 3-amino-1-phenylbutane + acetone
show the reaction diagram
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pyruvate + isopropylamine = L-alanine + acetone
show the reaction diagram
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(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + H2O = (-)-geosmin + acetone
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (34 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
increases the activity of the oxidized truncated enzyme form, optimal concentration 15%
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125% activity at 20% (v/v) acetone
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3.8fold increase in activity, 1 ml solvent added to 2 ml 50 mM phosphate buffer
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10% v/v, 5.7fold activation
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activates best at 5% v/v
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10% v/v, activation
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15%, 1.2fold activation. Strong decrease in activity above 15%
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activates
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25%, 2.45fold stimulation
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15% v/v, 128% of initial activity, 30% v/v, 155% of initial activity
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10% v/v, 570% of initial activity, 30% v/v, 53% of initial activity
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10% (v/v): 102% activity compared to no addition
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30% activation at 5%
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hydrolysis activity is enhanced in the presence of non-acceptor type organic solvents such as hexane, cyclohexane, diethylether, and acetone
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5%, 4.3fold activation of activity with carboxymethyl cellulose, slight activation of xylanase activity (to 104.6% of control), fusion enzyme (EG-M-Xyn) of endoglucanase (cellulase) from Teleogryllus emma and xylanase from Thermomyces lanuginosus
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activates the wild-type enzyme and mutant Man5DELTACBM at 40-60% v/v, no effect on mutant Man5DELTACL
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5%, 4.3fold activation of activity with carboxymethyl cellulose, slight activation of xylanase activity (to 104.6% of control), fusion enzyme (EG-M-Xyn) of endoglucanase (cellulase) from Teleogryllus emma and xylanase from Thermomyces lanuginosus
noncompetitive activator with respect to ethanolamine
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9.0fold
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Inhibitor in Enzyme-catalyzed Reactions (114 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
at 25% v/v and above
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at high concentrations of e.g. 3.4 M
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competitive for diacetyl, uncompetitive for NADH
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40% (v/v), 40% activity
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20% (v/v), 40% loss of activity
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38.3% residual activity at 10% (v/v)
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1% residual activity at 50% (v/v)
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inactivation, enzyme regains activity after removal of ketone
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25%, 62% inhibition
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competitive inhibition
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inhibits competitively against 2-nitropropane, no inhibitory effect against O2
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inhibits at 20% v/v
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45% inhibition at 10% concentration as co-solvent inpresence of substrate, 93% in absence of substrate
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10%, v/v, complete inhibition of hydroxylation
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increasing solvent concentration up to 80% (v/v) yields a gradual reduction in the activity of the soluble and cross-linked enzyme forms, the cross-linked enzyme aggregate shows about 40% residual activity after incubation in acetone for about 34 h
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10% (v/v), 21% inhibition
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22% residual activity after 30 min incubation at 30% (v/v)
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inhibition of microsomal enzyme
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10%, liver
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precipitation with acetone completely inhibits enzyme activity
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30% and 40% inhibition of isozyme UGT2B15 at 1%, respectively; 30% and 40% inhibition of isozyme UGT2B17 at 1%, respectively
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20% v/v, 69% inhibition
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20% v/v, 37% inhibition
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in acetone the activity of the enzyme decreases to 30-34% of the original activity
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activates at lower concentration, Chlase2 reaches its maximal activity in 40% acetone, in 40-60% acetone the activity is reduced, overview
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92% inhibition at 75% v/v
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82% inhibition at 10% (vol/vol)
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about 70% residual activity at 1 mM
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at 37°C, 1 mM reduces activity by 82%
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20% (v/v), 2 h, 20°C, 12% loss of activity
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20%, 95% inhibition
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40%, relative activity is decreased to 87%
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68.3% and 62% residual activity at 2.5 mM with 4-nitrophenyl beta-D-glucopyranoside and cellobioside as substrate, respectively
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inhibition at low concentrations
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inhibits 15% and 50% at 5% and 10% v/v, respectively
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10% (v/v), about% inhibition
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reduces the activity by 85% at 1.25% v/v, by 50% at 3.75% v/v, and by 56% at 6.25% v/v
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upon permeabilization
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inhibition up to 10%, v/v
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10%, complete inhibition; complete inhibition at 10% acetone
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2% (v/v), 70.3% inhibition
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inactivation by 50% acetone
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strong inhibition of cardiac myosin at alkaline pH, weak inhibition of skeletal myosin at alkaline pH
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Metals and Ions (2 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
15% or 30% v/v, 1.2fold activation
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activates by 35% at 5% v/v
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3D Structure of Enzyme-Ligand-Complex (PDB) (27 results)

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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (15 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
161.5
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pH 5.8, 37°C
1.33
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KM Value (25 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.065
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pH 6.0, 30°C

Ki Value (4 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.01
-
pH and temperature not specified in the publication

IC50 Value (1 result)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.011
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pH and temperature not specified in the publication

References & Links

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Links to other databases for acetone

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ChEBI
PubChem
ChEBI
PubChem