Ligand acetone

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.

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

Show all pahtways known for Show all pathways known for acetone

Roles as Enzyme Ligand

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

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
-
acetone + NADPH + H+ + O2 = methyl acetate + NADP+ + H2O
show the reaction diagram
-
cyanide + acetone = 2-hydroxy-2-methylpropanenitrile
show the reaction diagram
-
acetone + CO2 + ATP + H2O = acetoacetate + AMP + phosphate
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (31 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-propanol + NADP+ = acetone + NADPH
show the reaction diagram
-
-
2-propanol + NAD(P)+ = propan-2-one + NAD(P)H + H+
show the reaction diagram
-
-
propan-2-ol + NADP+ = acetone + NADPH + H+
show the reaction diagram
-
-
isopropanol + O2 = 2-propanone + H2O2
show the reaction diagram
-
-
2-propanol + O2 = propan-2-one + H2O2
show the reaction diagram
-
-
(+)-columbianetin + [reduced NADPH-hemoprotein reductase] + O2 = angelicin + acetone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
acetoacetate + H+ = acetone + CO2
show the reaction diagram
-
2-hydroxy-2-methylpropanenitrile = cyanide + acetone
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (31 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetone + NADH + H+ = ? + NAD+
show the reaction diagram
-
acetone + NADPH + H+ = propan-2-ol + NADP+
show the reaction diagram
-
propan-2-one + NADH + H+ = propan-2-ol + NAD+
show the reaction diagram
-
acetone + NADPH + H+ = propan-2-ol + NADP+
show the reaction diagram
-
acetone + NADPH + H+ + O2 = methyl acetate + NADP+ + H2O
show the reaction diagram
-
pyruvate oxime + acetone = pyruvate + acetoxime
show the reaction diagram
-
cyanide + acetone = 2-hydroxy-2-methylpropanenitrile
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (147 results)

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

Activator in Enzyme-catalyzed Reactions (31 results)

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

Inhibitor in Enzyme-catalyzed Reactions (101 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
at 25% v/v and above
-
at high concentrations of e.g. 3.4 M
-
competitive for diacetyl, uncompetitive for NADH
-
40% (v/v), 40% activity
-
20% (v/v), 40% loss of activity
-
38.3% residual activity at 10% (v/v)
-
1% residual activity at 50% (v/v)
-
inactivation, enzyme regains activity after removal of ketone
-
25%, 62% inhibition
-
competitive inhibition
-
inhibits competitively against 2-nitropropane, no inhibitory effect against O2
-
inhibits at 20% v/v
-
45% inhibition at 10% concentration as co-solvent inpresence of substrate, 93% in absence of substrate
-
10%, v/v, complete inhibition of hydroxylation
-
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
-
10% (v/v), 21% inhibition
-
22% residual activity after 30 min incubation at 30% (v/v)
-
inhibition of microsomal enzyme
-
10%, liver
-
precipitation with acetone completely inhibits enzyme activity
-
30% and 40% inhibition of isozyme UGT2B15 at 1%, respectively; 30% and 40% inhibition of isozyme UGT2B17 at 1%, respectively
-
20% v/v, 69% inhibition
-
20% v/v, 37% inhibition
-
in acetone the activity of the enzyme decreases to 30-34% of the original activity
-
activates at lower concentration, Chlase2 reaches its maximal activity in 40% acetone, in 40-60% acetone the activity is reduced, overview
-
92% inhibition at 75% v/v
-
82% inhibition at 10% (vol/vol)
-
at 37C, 1 mM reduces activity by 82%
-
20%, 95% inhibition
-
inhibition at low concentrations
-
inhibits 15% and 50% at 5% and 10% v/v, respectively
-
about 30% residual activity at 10% (v/v)
-
10% (v/v), about% inhibition
-
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
-
upon permeabilization
-
inhibition up to 10%, v/v
-
10%, complete inhibition; complete inhibition at 10% acetone
-
strong inhibition of cardiac myosin at alkaline pH, weak inhibition of skeletal myosin at alkaline pH
-
inactivation by 50% acetone
-

Metals and Ions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
15% or 30% v/v, 1.2fold activation
-

3D Structure of Enzyme-Ligand-Complex (PDB) (26 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (15 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
161.5
-
pH 5.8, 37C
1.33
-
-

KM Value (25 results)

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

Ki Value (4 results)

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)

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

References & Links

Links to other databases for acetone

ChEBI
PubChem
ChEBI
PubChem