Ligand acrolein

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Basic Ligand Information

Molecular Structure
Picture of acrolein (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C3H4O
acrolein
HGINCPLSRVDWNT-UHFFFAOYSA-N
Synonyms:
1,2-propenal, 2-Propen-1-al, 2-propenal, 2-propene-1-al, 3-alpha,beta-unsaturated aldehyde, acrylaldehyde, prop-2-en-1-al, prop-2-enal, propenal

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
acrolein + NADPH + H+ = ? + NADP+
-
show the reaction diagram
NADPH + H+ + acrolein = NADP+ + propionaldehyde
-

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
allyl alcohol + NAD+ = acrolein + NADH
-
-
show the reaction diagram
allyl alcohol + NADP+ = acrolein + NADPH
-

Substrate in Enzyme-catalyzed Reactions (30 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
acrolein + NADPH + H+ = ?
-
show the reaction diagram
acrolein + NADPH = propenol + NADP+
-
show the reaction diagram
acrolein + NADPH + H+ = prop-2-en-1-ol + NADP+
-
show the reaction diagram
acrylaldehyde + NAD+ + H2O = acrylate + NADH
-
show the reaction diagram
acrolein + NAD+ + H2O = ? + NADH + H+
-
show the reaction diagram
formaldehyde + H2O + acrolein = formate + allyl alcohol
-
show the reaction diagram
acrolein + NADPH + H+ = ? + NADP+
-
show the reaction diagram
1,2-propenal + NAD(P)H = propanal + NAD(P)+
-
show the reaction diagram
acrolein + NADPH = propanal + NADP+
-
show the reaction diagram
acrolein + methyl viologen = ?
-
show the reaction diagram
acrolein + reduced methylviologen = ? + oxidized methylviologen
-
show the reaction diagram
propenal + NADPH = propanal + NADP+
-
show the reaction diagram
NADPH + H+ + acrolein = NADP+ + propionaldehyde
-
show the reaction diagram
cyanide + acrolein = (2R)-2-hydroxybut-3-enenitrile
-

Product in Enzyme-catalyzed Reactions (18 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
2-propene-1-ol + NAD+ = 2-propene-1-al + NADH
-
-
show the reaction diagram
allyl alcohol + NAD+ = prop-2-enal + NADH + H+
-
-
show the reaction diagram
2-propen-1-ol + NADP+ = acrylaldehyde + NADPH
-
show the reaction diagram
allyl alcohol + NADP+ = acrylaldehyde + NADPH
-
show the reaction diagram
allyl alcohol + O2 = acrolein + H2O2
-
-
show the reaction diagram
allyl alcohol + ferricyanide = acrolein + ferricyanide
-
-
show the reaction diagram
allyl alcohol + ferricyanide = prop-2-enal + ferrocyanide
-

Activator in Enzyme-catalyzed Reactions (1 result)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
activates MMP-9 via EGFR/MAPK signaling and stimulation of pro-MMP-9 cleavage
-

Inhibitor in Enzyme-catalyzed Reactions (13 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
irreversible inhibition
-
irreversible, noncompetitive, IC50: 0.015 mM
-
irreversible inhibition
-
treatment of intact chloroplast
-
4% remaining activity at 0.5 mM, potent irreversible time-dependent inhibitor, addition of 1 mM vanadate slows inactivation of PTP1B by 0.5 mM acrolein
-
acrolein in cigarette smoke in part inhibits LTA4H peptidase activity
-
carbonyl modification with 0.1 mM
-
irreversible, no inactivation after prolonged incubation with glycidol phosphate and glycidaldehyde
-
79% inhibition at 0.03 mM
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (16 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
at pH 7.4 and 37°C
0.035
-
pH 7.0, 37°C
62.5
-
-
2.4
-
in 0.1 M potassium phosphate, pH 7.4
0.27
-
-
3.72
-
30°C
3.67
-
pH 6
0.667
-
pH 7.0, 25°C
pH 7, 25°C, mutant T53F
39.74
-
pH 7, 25°C, mutant T59F
1.25
-
pH 7, 25°C, wild-type
1.66
-
pH 7.3
at pH 6.0 and 25°C

KM Value (21 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
at pH 7.4 and 37°C
0.014
-
pH 7.0, 37°C
4.81
-
-
13
-
in 0.1 M potassium phosphate, pH 7.4
0.12
-
wild type isoform ALDH1A1, in 100 mM sodium diphosphate (pH 9.5), at 25°C
0.009
-
37°C, pH 7.0
-
0.15
-
pH 6
4.65
-
pH 7.0, 25°C
30°C
0.15
-
in 0.1 M phosphate buffer pH 6.4, at 22°C
5.6
-
22°C, pH 6.4
5.6
-
pH 7, 25°C, mutant T53F
2.3
-
pH 7, 25°C, mutant T59F
0.86
-
pH 7, 25°C, wild-type
1.45
-
pH 7.3
0.109
-
at pH 6.0 and 25°C

Ki Value (2 results)

COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
in sodium acetate (100 mM), bis-Tris (50 mM), Tris (50 mM), diethylenetriaminepentaacetic acid (5 mM), and 2,5-dimethylfuran (5% v/v), at pH 7 and 25°C
0.00023
-
pH 6.3, 38°C
0.447
-

IC50 Value (1 result)

COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
irreversible, noncompetitive, IC50: 0.015 mM
0.015
-

References & Links

Links to other databases for acrolein

ChEBI
PubChem
-
PubChem