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(a)
OH
Cl
S
Cl
Cl
Cl
S
P O
O
Cl
Cl
Cl
III
HO
S
O
O N
I
II
P
O
OH
+
P
O
HO
O
N
Cl
N
Cl
HO
N
Cl
Cl
O
HO
O
UDPGA
Cl
C2
C1
O
OH
C3
C4
C5
IV
GSH
IV
GSH
Glu
S
Cl
P
Cl
Cl
Cl
S
O
Cl
Cl
Cl
S
Cl
O
P
O
O
S
N
S
O
O
NH
P
N
S
O
O O
P
O
O
HO
N
S
O
NH
O
O
O
S
O
NH
NH 2
HO O
N
O
O
O
NH
O
NH
OH
HO
C6
C8
C9
C7
OH
OH
OH OH
Gly
O
III
O
NH 2
NH 2
**
OH
UDPGA
OH
Glu/Gly
DETP
Gly
Cl
Cl
Cl
Cl
S
S
O
O
Glu/Gly
P
P
O
OH
Cl
N
S
Cl
O
O O
O O
N
S
O
OH
O
NH 2
Cl
Cl
NH
S
O
C13
HO
C12
N
S
O
NH
P
O
HO
O
OH
NH
N
S
O
NH 2
O
OH
?
NH 2
C10
Glu/DETP
OH
C11
O
NH 2
O Cl
P
Cl
O
OH
DETP
O O
N
S
OH
O
Gly/Gly
NH 2
*
Cl
Cl
O
O5
Cl
Cl
O
HO
S
S
OH
N
NH
HO
DETP
N
S
OH
NH 2
O P
C15
C14
O
Figure 9.3 ( a) In vitro metabolism of chlorpyrifos in human hepatocytes. Adapted from Choi et al. (2006) . (b) In vitro metabolism of chlorpyrifos
oxon in human hepatocytes. Adapted from Choi et al. (2006).
 
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