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Canalicular
multispecific
organic anion
transporter 2
Solute carrier
family 22
member 7
Cytochrome P450
2C9
Cytochrome P450
2C19
Cytochrome P450
2C19
UDP-
glucuronosyltransferase
2B11
Cytochrome P450
2C19
Cytochrome P450
2C19
Cytochrome P450
1A2
UDP-
glucuronosyltransferase
2B11
Sulfotransferase
1A1
Sulfotransferase
1A1
Cytochrome P450
2C9
Cytochrome P450
2C9
Cytochrome P450
2C9
Cytochrome P450
2C9
Cytochrome P450
2C9
Cytochrome P450
2C9
Cytochrome P450
2C9
Omeprazole
Omeprazole
Omeprazole
Omeprazole
Warfarin
Warfarin
O2
FMNH2
S-6-
Hydroxywarfarin
Flavin
Mononucleotide
H2 O
H+
FMNH2
O2
S-4'-
Hydroxywarfarin
Flavin
Mononucleotide
H2 O
H+
FMNH2
O2
R-4'-
Hydroxywarfarin
Flavin
Mononucleotide
H2 O
H+
Uridine
diphosphate
glucuronic acid
R-4'-
Hydroxywarfarin
glucuronide
Uridine
5'-diphosphate
H+
O2
FMNH2
R-6-
Hydroxywarfarin
H2 O
Flavin
Mononucleotide
H+
O2
FMNH2
R-8-
Hydroxywarfarin
H2 O
Flavin
Mononucleotide
H+
FMNH2
O2
R-7-
Hydroxywarfarin
H2 O
Flavin
Mononucleotide
H+
Uridine
diphosphate
glucuronic acid
R-7-
Hydroxywarfarin
glucuronide
Uridine
5'-diphosphate
H+
Phosphoadenosine
phosphosulfate
R-7-
Hydroxywarfarin
sulfate
Adenosine
3',5'-diphosphate
H+
Phosphoadenosine
phosphosulfate
R-6-
Hydroxywarfarin
sulfate
Adenosine
3',5'-diphosphate
H+
O2
FMNH2
S-7-
Hydroxywarfarin
Flavin
Mononucleotide
H2 O
H+
O2
FMNH2
(R)9-
hydroxywarfarin
H2 O
Flavin
Mononucleotide
H+
FMNH2
O2
(S)9-
hydroxywarfarin
H2 O
Flavin
Mononucleotide
H+
FMNH2
O2
R-Warfarin-R-
Alcohol
H2 O
Flavin
Mononucleotide
H+
FMNH2
O2
S-Warfarin-R-
Alcohol
Flavin
Mononucleotide
H2 O
H+
NADH
H2 O
NAD
R-Warfarin-S-
Alcohol
NADH
H2 O
S-Warfarin-S-
Alcohol
NAD
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Cytosol
Hepatocyte
Intestinal Epithelial Cell
Endoplasmic Reticulum
Oral administration
ABCC3
SLC22A7
CYP2C9
CYP2C19
CYP2C19
UGT2B11
CYP2C19
CYP2C19
CYP1A2
UGT2B11
SULT1A1
SULT1A1
CYP2C9
CYP2C9
CYP2C9
CYP2C9
CYP2C9
CYP2C9
CYP2C9
Omeprazole
Omeprazole
Omeprazole
Omeprazole
Warfarin
Warfarin
Oxygen
FMNH2
S-6-
Hydroxywarfarin
Flavin
Mononucleotide
Water
Hydrogen Ion
FMNH2
Oxygen
S-4'-
Hydroxywarfarin
Flavin
Mononucleotide
Water
Hydrogen Ion
FMNH2
Oxygen
R-4'-
Hydroxywarfarin
Flavin
Mononucleotide
Water
Hydrogen Ion
Uridine
diphosphate
glucuronic acid
R-4'-
Hydroxywarfarin
glucuronide
Uridine
5'-diphosphate
Hydrogen Ion
Oxygen
FMNH2
R-6-
Hydroxywarfarin
Water
Flavin
Mononucleotide
Hydrogen Ion
Oxygen
FMNH2
R-8-
Hydroxywarfarin
Water
Flavin
Mononucleotide
Hydrogen Ion
FMNH2
Oxygen
R-7-
Hydroxywarfarin
Water
Flavin
Mononucleotide
Hydrogen Ion
Uridine
diphosphate
glucuronic acid
R-7-
Hydroxywarfarin
glucuronide
Uridine
5'-diphosphate
Hydrogen Ion
Phosphoadenosine
phosphosulfate
R-7-
Hydroxywarfarin
sulfate
Adenosine
3',5'-diphosphate
Hydrogen Ion
Phosphoadenosine
phosphosulfate
R-6-
Hydroxywarfarin
sulfate
Adenosine
3',5'-diphosphate
Hydrogen Ion
Oxygen
FMNH2
S-7-
Hydroxywarfarin
Flavin
Mononucleotide
Water
Hydrogen Ion
Oxygen
FMNH2
(R)9-
hydroxywarfarin
Water
Flavin
Mononucleotide
Hydrogen Ion
FMNH2
Oxygen
(S)9-
hydroxywarfarin
Water
Flavin
Mononucleotide
Hydrogen Ion
FMNH2
Oxygen
R-Warfarin-R-
Alcohol
Water
Flavin
Mononucleotide
Hydrogen Ion
FMNH2
Oxygen
S-Warfarin-R-
Alcohol
Flavin
Mononucleotide
Water
Hydrogen Ion
NADH
Water
NAD
R-Warfarin-S-
Alcohol
NADH
Water
S-Warfarin-S-
Alcohol
NAD
ABCC3
SLC22A7
CYP2C9
CYP2C19
CYP2C19
UGT2B11
CYP2C19
CYP2C19
CYP1A2
UGT2B11
SULT1A1
SULT1A1
CYP2C9
CYP2C9
CYP2C9
CYP2C9
CYP2C9
CYP2C9
CYP2C9
Ompz
Ompz
Ompz
Ompz
Warfari
Warfari
O2
FMNH2
S6H
FlvnMnt
H2 O
H+
FMNH2
O2
S4H
FlvnMnt
H2 O
H+
FMNH2
O2
R4H
FlvnMnt
H2 O
H+
UDPGlcA
R-4-H g
UDP
H+
O2
FMNH2
R6H
H2 O
FlvnMnt
H+
O2
FMNH2
R8H
H2 O
FlvnMnt
H+
FMNH2
O2
R7H
H2 O
FlvnMnt
H+
UDPGlcA
R-7-H g
UDP
H+
Paps
R-7-H s
A3'5'PP
H+
Paps
R-6-H s
A3'5'PP
H+
O2
FMNH2
S-7-Hyd
FlvnMnt
H2 O
H+
O2
FMNH2
(R)-hyd
H2 O
FlvnMnt
H+
FMNH2
O2
(S)-hyd
H2 O
FlvnMnt
H+
FMNH2
O2
R-W-R-A
H2 O
FlvnMnt
H+
FMNH2
O2
S-W-R-A
FlvnMnt
H2 O
H+
NADH
H2 O
NAD
R-W-S-A
NADH
H2 O
S-W-S-A
NAD
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Heme
Cytosol
Hepatocyte
Intestinal Epithelial Cell
Endoplasmic Reticulum
Oral administration
ABCC3
SLC22A7
CYP2C9
CYP2C19
CYP2C19
UGT2B11
CYP2C19
CYP2C19
CYP1A2
UGT2B11
SULT1A1
SULT1A1
CYP2C9
CYP2C9
CYP2C9
CYP2C9
CYP2C9
CYP2C9
CYP2C9
Ompz
Ompz
Ompz
Ompz
Warfari
Warfari
O2
FMNH2
S6H
FlvnMnt
H2O
H+
FMNH2
O2
S4H
FlvnMnt
H2O
H+
FMNH2
O2
R4H
FlvnMnt
H2O
H+
UDPGlcA
R-4-H g
UDP
H+
O2
FMNH2
R6H
H2O
FlvnMnt
H+
O2
FMNH2
R8H
H2O
FlvnMnt
H+
FMNH2
O2
R7H
H2O
FlvnMnt
H+
UDPGlcA
R-7-H g
UDP
H+
Paps
R-7-H s
A3'5'PP
H+
Paps
R-6-H s
A3'5'PP
H+
O2
FMNH2
S-7-Hyd
FlvnMnt
H2O
H+
O2
FMNH2
(R)-hyd
H2O
FlvnMnt
H+
FMNH2
O2
(S)-hyd
H2O
FlvnMnt
H+
FMNH2
O2
R-W-R-A
H2O
FlvnMnt
H+
FMNH2
O2
S-W-R-A
FlvnMnt
H2O
H+
NADH
H2O
NAD
R-W-S-A
NADH
H2O
S-W-S-A
NAD