Ligand styrene oxide

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Basic Ligand Information

Molecular Structure
Picture of styrene oxide (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H8O
styrene oxide
AWMVMTVKBNGEAK-UHFFFAOYSA-N
Synonyms:
(R,S)-styrene oxide, 2-phenyloxirane, 7,8-styrene oxide, epoxyethyl benzene, phenylethylenoxide, styrene-7,8-oxide, styrene 1',2'-oxide, styrene 7,8-oxide, styrene epoxide

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
styrene oxide + H2O = styrene glycol
-

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
styrene + NADH + H+ + O2 = styrene epoxide + NAD+ + H2O
-
-
show the reaction diagram
styrene + FADH2 + O2 = styrene oxide + FAD + H2O
-

Substrate in Enzyme-catalyzed Reactions (23 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
styrene 1',2'-oxide + 1,4-dithiothreitol = styrene + oxidized dithiothreitol
-

Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
styrene + tert-butyl hydroperoxide = styrene oxide + ?
-
-
show the reaction diagram
styrene + KBr + H2O2 = 2-bromo-1-phenylethan-1-ol + 2-phenyloxirane + 2 H2O
-
-
show the reaction diagram
styrene + tert-butyl hydroperoxide = epoxyethyl benzene + ?
-
-
show the reaction diagram
styrene + NADH + H+ + O2 = styrene epoxide + NAD+ + H2O
-
show the reaction diagram
styrene + NAD(P)H + O2 = styrene epoxide + NAD(P)+ + H2O
-
-
show the reaction diagram
styrene + FADH2 + O2 = styrene oxide + FAD + H2O
-
-
show the reaction diagram
styrene + O2 + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ = styrene oxide + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O
-

Activator in Enzyme-catalyzed Reactions (1 result)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
slightly activating at 0.1 mM, inhibitory at 0.2 mM
-

Inhibitor in Enzyme-catalyzed Reactions (8 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
marked inhibition; marked inhibition
-
slightly activating at 0.1 mM, inhibitory at 0.2 mM
-
inhibits hydration of trans-9,10-epoxystearate
-
inhibits hydration of estroxide and androstene oxide
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (9 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
isoform GSTM2, at pH 7.4 and 25°C
2.4
-
isoform GSTM3, at pH 7.4 and 25°C
2.4
-
isoform GSTM4, at pH 7.4 and 25°C
3.13
-
isoform GSTM5, at pH 7.4 and 25°C
4.12
-
isoform GSTT1, at pH 7.4 and 25°C
2.22
-
isoform GSTT4, at pH 7.4 and 25°C
1.78
-
pH 7.4, mutant N55A
0.002
-
pH 7.4, mutant Y53F
0.176
-
pH 7.4, wild-type
0.47
-

KM Value (19 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
-
0.065
-
isoform GSTT4, at pH 7.4 and 25°C
0.183
-
isoform GSTT1, at pH 7.4 and 25°C
0.16
-
isoform GSTM5, at pH 7.4 and 25°C
0.09
-
isoform GSTM4, at pH 7.4 and 25°C
0.365
-
isoform GSTM3, at pH 7.4 and 25°C
0.11
-
isoform GSTM2, at pH 7.4 and 25°C
0.064
-
-
3.4
-
microsomal enzyme
0.143
-
enzyme from untreated animals
1.98
-
enzyme from clofibbrate-treated animals
1.36
-
cytosolic enzyme
0.517
-
pH 7.4, mutant N55A
1.4
-
pH 7.4, mutant Y53F
3.7
-
pH 7.4, wild-type
1.4
-
pH 7.0, 25°C
0.077
-

References & Links

Links to other databases for styrene oxide

ChEBI
PubChem
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PubChem