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
Pathway Source
Pathways
KEGG
Drug metabolism - cytochrome P450, Hepatocellular carcinoma, Pathways in cancer
MetaCyc
detoxification of reactive carbonyls in chloroplasts

Roles as Enzyme Ligand

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

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EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
acrolein + NADPH + H+ = ? + NADP+
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show the reaction diagram
NADPH + H+ + acrolein = NADP+ + propionaldehyde
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In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
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show the reaction diagram
allyl alcohol + NAD+ = acrolein + NADH
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-
show the reaction diagram
allyl alcohol + NADP+ = acrolein + NADPH
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Substrate in Enzyme-catalyzed Reactions (30 results)

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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
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show the reaction diagram
acrolein + NAD+ + H2O = ? + NADH + H+
-
show the reaction diagram
formaldehyde + H2O + acrolein = formate + allyl alcohol
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show the reaction diagram
acrolein + NADPH + H+ = ? + NADP+
-
show the reaction diagram
1,2-propenal + NAD(P)H = propanal + NAD(P)+
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show the reaction diagram
acrolein + NADPH = propanal + NADP+
-
show the reaction diagram
acrolein + methyl viologen = ?
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show the reaction diagram
acrolein + reduced methylviologen = ? + oxidized methylviologen
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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
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Product in Enzyme-catalyzed Reactions (18 results)

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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
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Activator in Enzyme-catalyzed Reactions (1 result)

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COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
activates MMP-9 via EGFR/MAPK signaling and stimulation of pro-MMP-9 cleavage
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Inhibitor in Enzyme-catalyzed Reactions (13 results)

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COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
irreversible inhibition
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irreversible, noncompetitive, IC50: 0.015 mM
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irreversible inhibition
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treatment of intact chloroplast
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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
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acrolein in cigarette smoke in part inhibits LTA4H peptidase activity
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carbonyl modification with 0.1 mM
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irreversible, no inactivation after prolonged incubation with glycidol phosphate and glycidaldehyde
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79% inhibition at 0.03 mM
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (16 results)

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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
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in 0.1 M potassium phosphate, pH 7.4
0.27
-
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3.72
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30°C
3.67
-
pH 6
0.667
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pH 7.0, 25°C
pH 7, 25°C, mutant T53F
39.74
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pH 7, 25°C, mutant T59F
1.25
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pH 7, 25°C, wild-type
1.66
-
pH 7.3
at pH 6.0 and 25°C

KM Value (21 results)

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

Ki Value (2 results)

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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
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pH 6.3, 38°C
0.447
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IC50 Value (1 result)

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COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
irreversible, noncompetitive, IC50: 0.015 mM
0.015
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References & Links

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Links to other databases for acrolein

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ChEBI
PubChem
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PubChem