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trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
overview about the regio- and stereospecificity for utilization of dihydrodiol derivatives as substrates
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
isoform DD3 probably identical with 3(17)alpha-hydroxysteroid dehydrogenase EC 1.1.1.59 and D-xylose dehydrogenase EC 1.1.1.179
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
structure analysis reveals that the enzyme belongs to the aldo-keto reductase superfamily, like 3alpha-hydroxysteroid dehydrogenase, 17beta-hydroxysteroid dehydrogenase, 20alpha-hydroxysteroid dehydrogenase, aldose reductase, and aldehyde reductase
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
structure analysis reveals that the enzyme belongs to the aldo-keto reductase superfamily, like 3alpha-hydroxysteroid dehydrogenase, 17beta-hydroxysteroid dehydrogenase, 20alpha-hydroxysteroid dehydrogenase, aldose reductase, and aldehyde reductase
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
enzyme termed 3alpha-hydroxysteroid/dihydrodiol dehydrogenase, structure-based catalytic mechanism analysis, ordered bi-bi mechanism
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
cofactor binding and catalytic triad, alpha/beta-barrel structure
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
enzyme is multifunctional: 3alpha-hydroxysteroid dehydrogenase activity, EC 1.1.1.50, dihydrodiol dehydrogenase activity, EC 1.3.1.20, and 9-, 11-, and15-hydroxyprostaglandin dehydrogenase activity, belongs to aldo-keto reductase superfamily
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
D-xylose dehydrogenase EC 1.1.1.179 and dihydrodiol dehydrogenase EC 1.3.1.20 both follow an ordered bi-bi mechanism and are thus considered the same enzyme
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
identical with D-xylose dehydrogenase EC 1.1.1.179
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
probably identical with aldehyde reductase EC 1.1.1.2
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
probably identical with D-xylose dehydrogenase EC 1.1.1.179
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
isoforms belong to aldo-keto reductase superfamily
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
termed AKR1C as member of the aldo-keto-superfamily, overview
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
the cytosolic, but not the microsomal, enzyme is identical with 3alpha-hydroxysteroid dehydrogenase EC 1.1.1.50
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
DD4 is identical with human chlordecone reductase and 3alpha-hydroxysteroid dehydrogenase type 1, EC 1.1.1.213, catalyzes the oxidoreduction of various 3alpha-hydroxysteroids including bile acids and belong to the aldo-keto reductase superfamily, in this concern termed AKR1C4
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
isoform DD1 is identical with 3alpha-hydroxysteroid dehydrogenase EC 1.1.1.50, while isoform DD3 is a unique benzene dihydrodiol-specific enzyme
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
-
-
-
-
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(R)-tetralol + NADP+
? + NADPH
(S)-(+)-1,2,3,4-tetrahydronaphth-1-ol + NADP+
? + NADPH
(S)-indan-1-ol + NADP+
? + NADPH
(S)-tetralol + NADP+
? + NADPH
1-acenaphthenol + NAD(P)+
?
1-acenaphthol + NADP+
acenaphthylen-1-ol + NADPH
-
-
-
-
?
1-indanol + NADP+
3H-inden-1-ol + NADPH
17beta-estradiol + NAD(P)+
?
2,3-heptanedione + NADPH
?
-
-
-
-
?
2,3-hexanedione + NADPH
?
2,3-pentanedione + NADPH
?
2-cyclohexen-1-ol + NADP+
2-cyclohexene-1-one + NADPH
-
NAD+
-
-
?
2-deoxy-D-glucose + NADP+
2-deoxy-D-glucono-1,5-lactone + NADPH + H+
3-deoxyglucosone + NADPH
?
-
-
-
-
?
3-keto steroid + NAD(P)H
3alpha-hydroxy steroid + NAD(P)+
3-nitrobenzaldehyde + NADPH
3-nitrobenzylalcohol + NADP+
-
-
-
-
?
3alpha-hydroxy steroid + NADP+
3-keto steroid + NADPH
4-carboxybenzaldehyde + NADPH
?
-
-
-
-
?
4-chromanol + NADP+
?
-
-
-
r
4-chromanol + NADP+
? + NADPH
4-nitrobenzaldehyde + NAD(P)H
4-nitrobenzylalcohol + NAD(P)+
5alpha-androstan-3,17-dione + NADPH
5alpha-androstan-3alpha-ol-17-one + NADP+
-
isoform DD1, identical with 3alpha-hydroxysteroid dehydrogenase EC 1.1.1.50
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
5beta-androstan-3alpha-ol-17-one + NADP+
5beta-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
5beta-dihydrocortisone + NADPH
?
-
-
-
-
?
5beta-pregnan-3,20-diol + NADP+
5beta-pregnan-20-ol-3-one + NADPH
5beta-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5beta-pregnan-20-one + NADP+
-
-
-
-
?
7alpha-hydroxy-5beta-cholestan-3-one + NADPH
?
-
-
-
-
?
acenaphthenequinone + NADPH
?
-
-
-
-
?
acetoin + NADP+
?
-
-
-
-
?
alicyclic alcohol + NAD(P)+
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
camphorquinone + NADPH
?
-
-
-
-
?
camphorquinone + NADPH + H+
?
enzyme has dehydrogenase and reductase activities, enzyme is identical to NADP+-dependent D-xylose dehydrogenase
-
-
?
chenodeoxycholic acid + NADP+
?
-
DD1
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
D-arabinose + NADP+
D-arabinono-1,4-lactone + NADPH
D-galactose + NADP+
D-galactono-1,5-lactone + NADPH
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
D-glucuronate + NADP+
D-glucurono-1,5-lactone + NADPH
-
isoform DD4 no activity
-
-
r
D-glyceraldehyde + NADPH
?
D-lactaldehyde + NADP+
?
-
-
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
deoxycholic acid + NADP+
?
-
DD1
-
-
?
dihydroxyacetone + NADPH
?
dihydroxyacetone phosphate + NADPH
?
-
-
-
-
?
DL-glyceraldehyde + NADPH
?
-
probable identity with aldehyde reductase EC 1.1.1.2
-
-
?
DL-glyceraldehyde-3-phosphate + NADPH
?
-
-
-
-
?
epitestosterone + NAD(P)+
?
-
isoform DD3: dihydrodiol dehydrogenase EC 1.3.1.20 and 3(17)alpha-hydroxysteroid dehydrogenase EC 1.1.1.59 activities reside on a single protein
-
-
?
ethyl pyruvate + NADPH
ethyl lactate + NADP+
-
-
-
-
?
glycolithocholic acid + NAD(P)+
3-oxo-glycocholanoic acid + NAD(P)H
-
NAD+ preferred as cofactor
-
-
?
L-glyceraldehyde + NADPH
?
L-lactaldehyde + NADP+
?
-
-
-
-
?
lithocholic acid + NADP+
?
methyl pyruvate + NADPH
methyl lactate + NADP+
-
-
-
-
?
methylglyoxal + NADPH
?
-
-
-
-
?
naphthalene dihydrodiol + NAD(P)+
?
naphthalene dihydrodiol + NADP+
? + NADPH + H+
-
-
-
-
?
phenyl-1,2-propanedione + NADPH
?
-
-
-
-
?
phenylglyoxal + NADPH
?
-
-
-
-
?
pyridine-3-aldehyde + NADPH
?
pyridine-4-aldehyde + NADPH
?
-
-
-
-
?
S-(+)-1,2,3,4-tetrahydronaphth-1-ol + NADP+
? + NADPH
succinic semialdehyde + NADPH
?
-
isoform DD4 low activity
-
-
?
taurochenodeoxycholic acid + NADP+
?
-
DD1, DD3
-
-
?
taurocholic acid + NADP+
?
-
DD1
-
-
?
taurolithocholic acid + NADP+
?
-
DD1, DD3
-
-
?
testosterone + NADPH + H+
4-androsten-3alpha,17beta-diol + NADP+
-
NAD+
-
-
?
tetrahydrodeoxycorticosterone + NAD(P)+
?
-
isoform DD3: dihydrodiol dehydrogenase EC 1.3.1.20 and 3(17)alpha-hydroxysteroid dehydrogenase EC 1.1.1.59 activities reside on a single protein
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
trans-1,2-dihydroxy-1,2-dihydrophenanthrene + NADPH
?
-
-
-
-
?
trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene + NADP+
benzo[a]-pyrene-7,8-dione + NADPH
DD1, DD2, DD4, 3alpha-hydroxysteroid/dihydrodiol dehydrogenase
product is potent carcinogen
?
trans-benzene dihydrodiol + NADP+
? + NADPH
trans-naphthalene dihydrodiol + NAD(P)+
?
[1R,2R]-trans-cyclohexanediol + NADP+
?
-
-
-
-
?
additional information
?
-
(R)-indan-1-ol + NADP+
?
-
-
-
-
?
(R)-indan-1-ol + NADP+
?
-
DD4, recombinant double mutant S145C/L311V
-
-
?
(R)-tetralol + NADP+
?
-
DD4, recombinant double mutant S145C/L311V
-
-
?
(R)-tetralol + NADP+
?
-
-
-
?
(R)-tetralol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(R)-tetralol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(S)-(+)-1,2,3,4-tetrahydronaphth-1-ol + NADP+
? + NADPH
-
-
-
?
(S)-(+)-1,2,3,4-tetrahydronaphth-1-ol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(S)-indan-1-ol + NADP+
?
-
DD3
-
-
?
(S)-indan-1-ol + NADP+
?
-
-
-
-
?
(S)-indan-1-ol + NADP+
?
-
-
-
?
(S)-indan-1-ol + NADP+
?
-
DD4, wild-type and recombinant double mutant S145C/L311V
-
-
?
(S)-indan-1-ol + NADP+
?
-
DD1, DD4, mutant CDD1-4, mutant CDD4-1
-
-
?
(S)-indan-1-ol + NADP+
?
recombinant DD1, DD1, DD2
-
-
?
(S)-indan-1-ol + NADP+
?
-
-
-
?
(S)-indan-1-ol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(S)-indan-1-ol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(S)-tetralol + NADP+
?
DD1, DD2, recombinant DD1
-
-
?
(S)-tetralol + NADP+
?
-
DD4, recombinant double mutant S145C/L311V
-
-
?
(S)-tetralol + NADP+
?
-
-
-
?
(S)-tetralol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(S)-tetralol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
1-acenaphthenol + NAD(P)+
?
-
-
-
-
?
1-acenaphthenol + NAD(P)+
?
-
DD3
-
-
?
1-acenaphthenol + NAD(P)+
?
recombinant: DD1, DD2, and 3alpha-hydroysteroid dehydrogenase/dihydrodiol dehydrogenase
-
-
?
1-acenaphthenol + NAD(P)+
?
-
-
-
-
?
1-indanol + NADP+
3H-inden-1-ol + NADPH
-
-
-
-
?
1-indanol + NADP+
3H-inden-1-ol + NADPH
-
-
-
?
17beta-estradiol + NAD(P)+
?
-
-
-
-
?
17beta-estradiol + NAD(P)+
?
-
isoform DD3: dihydrodiol dehydrogenase EC 1.3.1.20 and 3(17)alpha-hydroxysteroid dehydrogenase EC 1.1.1.59 activities reside on a single protein
-
-
?
2,3-hexanedione + NADPH
?
-
-
-
-
?
2,3-hexanedione + NADPH
?
-
-
-
-
?
2,3-pentanedione + NADPH
?
-
-
-
-
?
2,3-pentanedione + NADPH
?
-
-
-
-
?
2-deoxy-D-glucose + NADP+
2-deoxy-D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
2-deoxy-D-glucose + NADP+
2-deoxy-D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
2-deoxy-D-glucose + NADP+
2-deoxy-D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
2-deoxy-D-glucose + NADP+
2-deoxy-D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
3-keto steroid + NAD(P)H
3alpha-hydroxy steroid + NAD(P)+
-
probably reversible reaction
-
-
?
3-keto steroid + NAD(P)H
3alpha-hydroxy steroid + NAD(P)+
-
-
-
r
3-keto steroid + NAD(P)H
3alpha-hydroxy steroid + NAD(P)+
-
reduces biologically important 3-oxo steroids of the androstane, pregnane, and cholane series
-
-
?
3alpha-hydroxy steroid + NADP+
3-keto steroid + NADPH
-
not, DD3
-
-
?
3alpha-hydroxy steroid + NADP+
3-keto steroid + NADPH
-
-
-
-
?
3alpha-hydroxy steroid + NADP+
3-keto steroid + NADPH
-
-
-
-
?
3alpha-hydroxy steroid + NADP+
3-keto steroid + NADPH
-
-
-
-
?
3alpha-hydroxy steroid + NADP+
3-keto steroid + NADPH
-
-
-
-
?
4-chromanol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
4-chromanol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
4-nitrobenzaldehyde + NAD(P)H
4-nitrobenzylalcohol + NAD(P)+
-
-
-
-
?
4-nitrobenzaldehyde + NAD(P)H
4-nitrobenzylalcohol + NAD(P)+
-
DD2, DD3
-
-
?
4-nitrobenzaldehyde + NAD(P)H
4-nitrobenzylalcohol + NAD(P)+
-
-
-
-
?
4-nitrobenzaldehyde + NAD(P)H
4-nitrobenzylalcohol + NAD(P)+
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
-
-
r
5beta-androstan-3,17-dione + NADPH
5beta-androstan-3alpha-ol-17-one + NADP+
-
-
-
-
?
5beta-androstan-3,17-dione + NADPH
5beta-androstan-3alpha-ol-17-one + NADP+
-
-
-
-
?
5beta-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
-
-
-
-
?
5beta-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
DD1, DD2, recombinant DD1
-
-
?
5beta-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
-
DD4 wild-type and mutants
-
-
?
5beta-pregnan-3,20-diol + NADP+
5beta-pregnan-20-ol-3-one + NADPH
-
-
-
-
?
5beta-pregnan-3,20-diol + NADP+
5beta-pregnan-20-ol-3-one + NADPH
DD1, DD2, recombinant DD1
-
-
?
alicyclic alcohol + NAD(P)+
?
-
not:
-
-
?
alicyclic alcohol + NAD(P)+
?
-
-
-
-
?
androsterone + NADPH
?
-
DD1, identical with 3alpha-hydroxysteroid dehydrogenase EC 1.1.1.50
-
-
?
androsterone + NADPH
?
-
-
-
-
?
androsterone + NADPH
?
-
DD4 wild-type and mutants
-
-
?
androsterone + NADPH
?
recombinant DD4
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
-
?
cholic acid + NADP+
?
-
DD1
-
-
?
cholic acid + NADP+
?
-
-
-
-
?
cholic acid + NADP+
?
-
DD4, wild-type and recombinant double mutant S145C/L311V
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
not:
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
not:
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
-
r
D-arabinose + NADP+
D-arabinono-1,4-lactone + NADPH
-
low activity
-
-
?
D-arabinose + NADP+
D-arabinono-1,4-lactone + NADPH
-
low activity
-
-
?
D-arabinose + NADP+
D-arabinono-1,4-lactone + NADPH
-
low activity
-
-
?
D-arabinose + NADP+
D-arabinono-1,4-lactone + NADPH
-
low activity
-
-
?
D-galactose + NADP+
D-galactono-1,5-lactone + NADPH
-
low activity
-
-
?
D-galactose + NADP+
D-galactono-1,5-lactone + NADPH
-
only isoform DD3
-
-
?
D-galactose + NADP+
D-galactono-1,5-lactone + NADPH
-
low activity
-
-
?
D-galactose + NADP+
D-galactono-1,5-lactone + NADPH
-
low activity
-
-
?
D-galactose + NADP+
D-galactono-1,5-lactone + NADPH
-
low activity
-
-
?
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
-
only isoform DD3
-
-
?
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
D-glyceraldehyde + NADPH
?
-
-
-
-
?
D-glyceraldehyde + NADPH
?
-
DD2 and DD3 show high activity, DD4 only shows low activity
-
-
?
D-glyceraldehyde + NADPH
?
-
-
-
-
?
D-ribose + NADP+
?
-
-
-
-
?
D-ribose + NADP+
?
-
-
-
-
?
D-ribose + NADP+
?
-
-
-
-
?
D-ribose + NADP+
?
-
-
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
also low activity with L-xylose
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
-
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
-
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
-
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
also low activity with L-xylose
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
also low activity with L-xylose
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
-
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
also low activity with L-xylose
-
-
?
diacetyl + NADPH
?
-
-
-
-
?
diacetyl + NADPH
?
-
-
-
-
?
diacetyl + NADPH
?
-
2,3-butanedione
-
-
?
dihydroxyacetone + NADPH
?
-
-
-
-
?
dihydroxyacetone + NADPH
?
-
-
-
-
?
L-glyceraldehyde + NADPH
?
-
-
-
-
?
L-glyceraldehyde + NADPH
?
-
DD2 and DD3 show high activity, DD4 only shows low activity
-
-
?
L-glyceraldehyde + NADPH
?
-
-
-
-
?
lithocholic acid + NADP+
?
-
DD1, DD3
-
-
?
lithocholic acid + NADP+
?
-
-
-
-
?
naphthalene dihydrodiol + NAD(P)+
?
-
-
-
-
?
naphthalene dihydrodiol + NAD(P)+
?
-
-
-
-
?
naphthalene dihydrodiol + NAD(P)+
?
-
-
-
-
?
naphthalene dihydrodiol + NAD(P)+
?
-
-
-
-
?
pyridine-3-aldehyde + NADPH
?
-
-
-
-
?
pyridine-3-aldehyde + NADPH
?
-
-
-
-
?
pyridine-3-aldehyde + NADPH
?
-
-
-
-
?
pyridine-3-aldehyde + NADPH
?
-
DD4 wild-type and mutants
-
-
?
S-(+)-1,2,3,4-tetrahydronaphth-1-ol + NADP+
? + NADPH
-
-
-
?
S-(+)-1,2,3,4-tetrahydronaphth-1-ol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
the reaction produces a ketol which then enolizes to the catechol
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
DD3
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
DD3: specific for, no activity towards other alcohols, aldehydes, ketones and quinones
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
-
r
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
DD1, DD2, recombinant DD1
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
the reaction produces a ketol which then enolizes to the catechol
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
-
r
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
the reaction produces a ketol which then enolizes to the catechol
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
the reaction produces a ketol which then enolizes to the catechol
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
the reaction produces a ketol which then enolizes to the catechol
-
?
trans-benzene dihydrodiol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
trans-benzene dihydrodiol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
trans-naphthalene dihydrodiol + NAD(P)+
?
-
-
-
-
?
trans-naphthalene dihydrodiol + NAD(P)+
?
-
DD3
-
-
?
trans-naphthalene dihydrodiol + NAD(P)+
?
-
-
-
-
?
trans-naphthalene dihydrodiol + NAD(P)+
?
-
-
-
-
r
trans-naphthalene dihydrodiol + NAD(P)+
?
-
-
-
-
?
trans-naphthalene dihydrodiol + NAD(P)+
?
-
-
-
-
?
trans-naphthalene dihydrodiol + NAD(P)+
?
-
-
-
-
?
trans-naphthalene dihydrodiol + NAD(P)+
?
-
-
-
-
?
trans-naphthalene dihydrodiol + NAD(P)+
?
-
-
-
-
?
trans-naphthalene dihydrodiol + NAD(P)+
?
-
-
-
-
?
additional information
?
-
-
metabolic inactivation of exogeneous xenobiotics
-
-
?
additional information
?
-
-
involved in the metabolism of steroid hormones and polycyclic aromatic hydrocarbons, and also in the reduction of ketone-containing drugs
-
-
?
additional information
?
-
-
involved in the metabolism of steroid hormones and polycyclic aromatic hydrocarbons, and also in the reduction of ketone-containing drugs
-
-
?
additional information
?
-
-
enzyme-mediated oxidative damage is involved in the hydroxychavicol and benzo[a]pyrene-induced toxic effects
-
-
?
additional information
?
-
-
the enzyme is a member of the aldo-keto reductase superfamily, which normally reduces polycyclic aromatic hydrocarbons in the liver, it plays an important role in detoxification
-
-
?
additional information
?
-
dihydrodiol dehydrogenase catalyzes the NADP+-linked oxidation of dihydrodiols of aromatic hydrocarbons to their corresponding catechols and is regarded as a toxication enzyme in the metabolism of carcinogenic polycyclic aromatic hydrocarbons because oxidation by the enzyme yields reactive and redox-active ortho-quinones and reactive oxygen species, broad substrate specificity indicates additional roles of the enzyme in the metabolism of endogenous and xenobiotic carbonyl compounds and the prevention of the development of glycation
-
-
?
additional information
?
-
dimeric dihydrodiol dehydrogenase catalyses the nicotinamide adenine dinucleotide phosphate NADP+-dependent oxidation of trans-dihydrodiols of aromatic hydrocarbons to their corresponding catechols, dimeric dihydrodiol dehydrogenase is also competent in the NADPH-driven reduction of a limited number of aldehyde and dicarbonyl compounds such as 3-deoxyglucosone, camphorquinone, and 3-nitrobenzaldehyde
-
-
?
additional information
?
-
no substrate: befunolol, prostaglandin D2, progesterone
-
-
?
additional information
?
-
no substrate: befunolol, prostaglandin D2, progesterone
-
-
?
additional information
?
-
-
metabolic inactivation of dihydrodiols or dihydrodiol epoxides derived from carcinogenic polycylic hydrocarbons
-
-
?
additional information
?
-
-
enzyme catalyzes formation of benz[a]anthracene-1,2-dihydrodiol which causes Cu[II]-mediated DNA damage including 8-oxo-7,8-dihydro-2-deoxyguanosine formation in the presence of NAD+
-
-
?
additional information
?
-
-
reduces biologically important 3-oxo steroids of the androstane, pregnane, and cholane series
-
-
?
additional information
?
-
-
detoxification of polycyclic aromatic trans-hydrodiols by formation of o-quinones from the reaction product of dihydrodiol oxidation
-
-
?
additional information
additional information
-
-
not: hydroxy steroids
-
-
?
additional information
additional information
-
-
xenobiotic acyclic alcohols (Japanese monkey)
-
-
?
additional information
additional information
-
-
3 forms: DD4 pI 4.2, DD3 pI 5.0 and DD2 pI 5.4, isoform DD4: strict specificity for benzene dihydrodiol and NADP+, and for reduced pyridine aldehydes, glyceraldehyde and, at low rate, for diacetyl, isoform DD3: oxidizes n-butanol, glycerol and sorbitol as well as benzene dihydrodiol in the presence of NADP+ or NAD+, and exhibits much higher reductase activity towards various aldehydes, aldoses and diacetyl
-
-
?
additional information
additional information
-
-
DD4 also catalyzes oxidoreduction of 3alpha-hydroxysteroids and bile acids and is thus thought to be identical with 3alpha-hydroxysteroid dehydrogenase EC 1.1.1.213
-
-
?
additional information
additional information
-
-
catalyzes oxidation of trans-dihydrodiols of aromatic hydrocarbons to corresponding catechols and oxidation of several pentoses
-
-
?
additional information
additional information
-
-
monomeric forms are identical with 3alpha-hydroxysteroid dehydrogenase EC 1.1.1.50 and provide a broad substrate specificity, while dimeric forms are identical with D-xylose dehydrogenase EC 1.1.1.179 and are active with trans-dihydrodiols and dicarbonyl compounds
-
-
?
additional information
additional information
-
-
not: hydroxy steroids
-
-
?
additional information
additional information
-
-
the enzyme transfers the 4-pro-R-hydrogen atom of NADPH to the carbonyl substrate
-
-
?
additional information
additional information
-
-
not: alcohols
-
-
?
additional information
additional information
-
-
NADP+ or NAD+ as cofactors
-
-
?
additional information
additional information
-
-
NADP+ or NAD+ as cofactors
-
-
?
additional information
additional information
-
-
regio- and stereospecificity
-
-
?
additional information
additional information
-
-
NADP+ or NAD+ as cofactors
-
-
?
additional information
additional information
-
-
oxidation of trans-dihydrodiols of polycyclic hydrocarbons and in this way suppression of formation of anti-diol epoxid carcinogens
-
-
?
additional information
additional information
-
-
overview about structure and utilization of trans-dihydrodiols as substrates
-
-
?
additional information
additional information
-
-
at least 2 proteins, monomeric form F2 and dimeric form F1, with both dihydrodiol dehydrogenase EC 1.3.1.20 and aldehyde reductase activity EC 1.1.1.2, F1: specifically oxidizes trans-hydrodiols of naphthalene and benzene strictly with NADP+ as cofactor, reduction of vicinal diketones, aromatic aldehydes and glyceraldes with NADPH as cofactor
-
-
?
additional information
additional information
-
-
not: hydroxy steroids
-
-
?
additional information
additional information
-
-
F2: high activity towards naphthalene dihydrodiol and some alcohols, low activity towards trans- and cis-benzene dihydrodiols and some alcohols, reduction of aldoses, vicinal diketones, aromatic aldehydes and glyceraldehydes with NADPH or NADH as cofactors
-
-
?
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1,7-phenanthroline
DD1, recombinant DD1, but DD2 less sensitive
1-Indanone
-
recombinant DD4
2,6-dihydroxyanthraquinone
3',3'',5',5''-tetrabromophenolphthalein
-
recombinant DD4
4-hydroxybenzaldehyde
-
-
4-hydroxybenzophenone
-
-
4-hydroxyphenylglyoxal
-
-
5,5'-dithiobis(2-nitrobenzoic acid)
5alpha-androstan-3,17-dione
-
DD3
5alpha-Androstan-3-beta-ol-17-one
-
-
5alpha-Pregnan-3beta-21-one
-
-
5beta-androstan-3,17-dione
-
DD3
5beta-Androstan-3alpha-ol-17-one
-
DD3
5beta-androstan-3beta-ol-17-one
-
-
5beta-Pregnan-3beta-ol-20-one
-
-
Benzo[a]pyrene-7,8-dione
-
-
Bromophenol blue
-
recombinant DD4
chenodeoxycholic acid
DD2 very sensitive, DD1 less sensitive, recombinant DD1
chrysin
inhibits enzyme expression at concentrations higher than 0.01 mM; inhibits enzyme expression at concentrations higher than 0.01 mM
cyclopentane-1,1-diacetic acid NaCl
-
inhibits only isoform F2
Dehydrolithocholic acid
-
DD2
diphosphate
-
high concentration: F2 slight inhibition, F1 stimulation
doxorubicin hydrochloride
-
50% inhibition at 0.000706 mM, parental 2008 cell, at 0.000377, 2008/C13* cell, at 0.000375 mM, 2008 cell expressing isoform 2
glutathione
-
wild-type and mutant C145S
Ibuprofen
very sensitive: DD2, less sensitive: DD1, recombinant DD1
KCl
-
increase in Km-value for D-xylose and NADP+
medroxyprogesterone
-
DD4 wild-type and mutants
Medroxyprogesterone acetate
-
recombinant: DD1, DD4, CDD1-4, CDD4-1
melphalan
-
50% inhibition at 0.009 mM, parental 2008 cell, at 0.0088, 2008/C13* cell, at 0.0057 mM, 2008 cell expressing isoform 2
N-ethylmaleimide
-
wild-type and mutant C145S
naphthalene-1,2-dione
-
-
p-chloromercuribenzene sulfonate
-
stronger effect on isoform F2
p-chloromercuribenzoate
-
stronger effect on isoform F1
p-chloromercuriphenyl sulfonate
paclitaxel
-
50% inhibition at 0.0000393 mM, parental 2008 cell, at 0.0000101, 2008/C13* cell, at 0.0000283 mM, 2008 cell expressing isoform 2
Phenol red
-
recombinant DD4
phenolphthalein phosphate
-
recombinant DD4
phosphate buffer
-
inhibitionn of mutant enzymes H79Q and Y180F
-
SO42-
-
inhibits only isoform F1
Thiol-blocking reagents
-
F1
-
Thymolphthalein
-
recombinant DD4
Ursodeoxycholic acid
very sensitiv: DD2, less sensitiv: DD1, recombinant DD1
ursodeoxylithocholic acid
-
DD2
vincristine
-
50% inhibition at 0.000021 mM, parental 2008 cell, at 0.000016, 2008/C13* cell, at 0.0000136 mM, 2008 cell expressing isoform 2
wogonin
inhibits enzyme expression at concentrations higher than 0.0025 mM; inhibits enzyme expression at concentrations higher than 0.0025 mM
1,10-phenanthroline
DD1, recombinant DD1, but DD2 less sensitive
1,10-phenanthroline
-
recombinant: DD1, DD4, CDD1-4, CDD4-1
17beta-estradiol
-
DD4, recombinant enzyme
2,6-dihydroxyanthraquinone
-
competitive inhibitor
2,6-dihydroxyanthraquinone
-
competitive inhibitor
4-hydroxyacetophenone
-
-
4-hydroxyacetophenone
-
competitive inhibitor
4-hydroxyacetophenone
-
-
4-hydroxyacetophenone
-
-
4-hydroxyacetophenone
-
inhibits dihydrodiol and D-xylose dehydrogenase activity
4-hydroxyacetophenone
-
competitive inhibitor
5,5'-dithiobis(2-nitrobenzoic acid)
-
i.e. DTNB, inhibits wild-type enzyme and mutant C145S
5,5'-dithiobis(2-nitrobenzoic acid)
-
inhibits DD1 and DD3, inhibition can be overcome by androsterone for DD1 and by benzenedihydrodiol for DD3, not vice versa
Barbital
-
DD2, DD4
Barbital
-
inhibits isoform F2
Betamethasone
-
DD4 wild-type and mutants
Betamethasone
-
DD4, recombinant enzyme
Betamethasone
-
recombinant: DD1, DD4, CDD1-4, CDD4-1
carboplatin
-
50% inhibition at 0.0358 mM, parental 2008 cell, at 0.578, 2008/C13* cell, at 0.0974 mM, 2008 cell expressing isoform 1, at 0.0871 mM, 2008 cell expressing isoform 2
carboplatin
-
50% inhibition at 0.036 mM, 2008 cells, at 0.578 mM, 2008/C13* cells, at 0.097 mM, cells constitutively overexpressing enzyme
cisplatin
-
50% inhibition at 0.0021 mM, parental 2008 cell, at 0.0186, 2008/C13* cell, at 0.0161 mM, 2008 cell expressing isoform 1, at 0.0062 mM, 2008 cell expressing isoform 2
cisplatin
-
50% inhibition at 0.002 mM, 2008 cells, at 0.019 mM, 2008/C13* cells, at 0.016 mM, cells constitutively overexpressing enzyme
dexamethasone
-
DD4 wild-type and mutants
dexamethasone
-
DD4, recombinant enzyme
Flufenamic acid
-
DD2
Flufenamic acid
-
DD4, recombinant enzyme
Flufenamic acid
DD1, DD2, recombinant DD1
Flufenamic acid
-
recombinant: DD1, DD4, CDD1-4, CDD4-1
Hexestrol
-
-
Hexestrol
-
DD4 wild-type and mutants
Hexestrol
-
DD4, recombinant enzyme
Hexestrol
DD1, DD2, recombinant DD1
Hexestrol
-
recombinant: DD1, DD4, CDD1-4, CDD4-1
Hexestrol
-
i.e. 4,4'-(1,2-diethyl-1,2-ethanediyl)bisphenol, inhibits isoform F2
indomethacin
-
-
indomethacin
-
DD4 wild-type and mutants
indomethacin
-
recombinant DD4
indomethacin
DD1, DD2, recombinant DD1
indomethacin
-
recombinant: DD1, DD4, CDD1-4, CDD4-1
indomethacin
-
cytosolic enzyme
indomethacin
-
inhibits both isoforms
isoascorbic acid
-
-
isoascorbic acid
competitive inhibitor
isoascorbic acid
-
competitive inhibitor
isoascorbic acid
-
inhibits dihydrodiol and D-xylose dehydrogenase activity
isoascorbic acid
-
competitive inhibitor
L-ascorbic acid
-
competitive inhibitor
L-ascorbic acid
-
competitive inhibitor
lithocholic acid
-
DD2
lithocholic acid
DD2, DD1, recombinant DD1
MgCl2
-
inhibition of mutant enzymes H79Q and Y180F
MgCl2
-
increase in Km-value for D-xylose and NADP+
NaCl
-
DD2, DD4
NaCl
-
high concentration: F2 inhibition, F1 stimulation
p-chloromercuriphenyl sulfonate
-
-
p-chloromercuriphenyl sulfonate
-
inhibits only DD3
Phenolphthalein
-
DD4 wild-type and mutants
Phenolphthalein
-
DD4, recombinant enzyme, inhibition mechanism
Phenolphthalein
-
recombinant: DD1, DD4, CDD1-4, CDD4-1
quercitrin
-
-
quercitrin
-
inhibits isoform F2 and slightly isoform F1
sorbinil
-
DD2, DD3 is more sensitive, DD4 no inhibition
sorbinil
-
inhibits isoform F1
Stilbestrol
-
-
additional information
-
DD3, product inhibition studies
-
additional information
-
DD4 is inhibited by steroidal anti-inflammatory drugs
-
additional information
-
DD2, product inhibition and inhibition mechanism of bile acids and anti-inflammatory drugs
-
additional information
-
further values for other cell lines
-
additional information
enzyme expression is not inhibited by baicalin and baicalein; enzyme expression is not inhibited by baicalin and baicalein
-
additional information
enzyme expression is not inhibited by baicalin and baicalein; enzyme expression is not inhibited by baicalin and baicalein
-
additional information
-
inhibition by nonsteroidal antiinflammatory drugs
-
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C145S
-
same sensitivity to SH-reagents as wild-type
C193S
-
no sensitivity to SH-reagents remaining
D50N
-
low dehydrogenase activity
H117Q
-
increased reductase activity
K84N
-
low dehydrogenase activity, no remaining reductase activity
Y55F
-
very low dehydrogenase activity
Y55H
-
decreased dehydrogenase activity, significant increased in reductase activity
L311V
-
native mutant with C to G replacement in DNA at position 931
L54V
-
DD1 mutant, increase in activity towards (S)-indan-1-ol and bile-acids, increased Km for trans-benzene dihydrodiol
S145C
-
native mutant with C to G replacement in DNA at position 434, no significant effect on activity
S145C/L311V
-
constructed double mutant with 3 to 5fold decreased activity for xenobiotic and steroidal substrates
A36D
production by site-directed mutagenesis
D280A
production by site-directed mutagenesis
F154A
production by site-directed mutagenesis
H76Q
production by site-directed mutagenesis
H79Q
production by site-directed mutagenesis
R37A
production by site-directed mutagenesis
R37D
production by site-directed mutagenesis
R41A
production by site-directed mutagenesis
R41D
production by site-directed mutagenesis
W125A
-
the mutation affects inhibition and substrate affinity
W125Y
production by site-directed mutagenesis
W254Y
production by site-directed mutagenesis
A36D
-
shows a decreased kcat value compared to the wild type enzyme
D280A
-
shows a decreased kcat value compared to the wild type enzyme
F154A
-
shows a decreased kcat value compared to the wild type enzyme
F279A
-
shows a decreased kcat value compared to the wild type enzyme
H76Q
-
shows a decreased kcat value compared to the wild type enzyme
K97M
-
shows a decreased kcat value compared to the wild type enzyme
K97R
-
shows a decreased kcat value compared to the wild type enzyme
R37A
-
shows a decreased kcat value compared to the wild type enzyme
R37D
-
shows a decreased kcat value compared to the wild type enzyme
R41A
-
shows a decreased kcat value compared to the wild type enzyme
R41D
-
shows a decreased kcat value compared to the wild type enzyme
W125Y
-
shows a decreased kcat value compared to the wild type enzyme
W254A
-
shows a decreased kcat value compared to the wild type enzyme
W254Y
-
shows a decreased kcat value compared to the wild type enzyme
Y180F
-
site-directed mutagenesis, very low activity
C170A
-
kinetically similar to wild-type
C217A
-
4fold increase in Km for 5alpha-androstan-3,17-dione and 2fold increase in Km for NADH
F279A
-
the mutation affects inhibition and substrate affinity
F279A
production by site-directed mutagenesis
K97M
-
mutant shows almost complete abrogation in activity for D-xylose oxidation and NADP+, and very poor activity with camphorquinone reduction and NADPH
K97M
production by site-directed mutagenesis
K97R
-
mutant shows almost complete abrogation in activity for D-xylose oxidation and NADP+, and very poor activity with camphorquinone reduction and NADPH
K97R
production by site-directed mutagenesis
R148A
-
activity and temperature stability are similar to the wild type enzyme
R148A
mutagenesis is performed using a QuickChange site-directed mutagenesis kit, dehydrogenase activity is comparable to that of the wild type
R148A/R202A
-
very low activity, the Vmax value of the mutant enzyme is 3.7fold lower than the wild type enzyme, displays significant temperature sensitivity
R148A/R202A
mutagenesis is performed using a QuickChange site-directedmutagenesis kit
R202A
-
activity and temperature stability are similar to the wild type enzyme
R202A
mutagenesis is performed using a QuickChange site-directed mutagenesis kit, dehydrogenase activity is comparable to that of the wild type
W254A
-
the mutation affects inhibition and substrate affinity
W254A
production by site-directed mutagenesis
H79Q
-
site-directed mutagenesis, moderate activity with 190fold increase in Km-value, inhibition by MgCl2 and potassium phosphate
H79Q
-
shows a decreased kcat value compared to the wild type enzyme
additional information
-
CDD1-4 mutant consisting of DD1 with C-terminal end of DD4 shows 10-37fold increase in Km for indan-1-ol and 1,2,3,4-tetrahydronaphth-1-ol and significantly decreased activity towards androstanes, higher activity with bile-acids and 5beta-steroid than DD1
additional information
-
CDD4-1 mutant consisting of DD4 with C-terminal end of DD1shows new stereospecificity toward indan-1-ol stereomers and increased Km-values with bile acids and 3-hydroxysteroids compared to DD4
additional information
-
constitutive overexpression of enzyme in 2008 cells leads to induction of cisplatin resistance. In cisplatin-resistant cell-line 2008/C13*, differential expression of enzyme and four more genes is found
additional information
-
knock down of enzyme isoform DHH1 expression by siRNA in CL-3 cells results in 1.4- to 2.2fold increase in DNA-benzo[a]pyrene adducts
additional information
-
overexpression of enzyme in lung adenocarcinoma cell lines results in a much higher resistance to doxorubicin, cisplatin and irradiation. Isoforms DDH2 and DDH1 transfectants show higher drug and radiation resistance than DDH3 transfectants
additional information
-
sequence analysis reveals high sequence homology between dimeric mammalian dihydrodiol dehydrogenases, but no homology with monomeric or cis-dihydrodiol-specific enzymes
additional information
-
sequence analysis
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Macaca fuscata
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-
brenda
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Ruditapes philippinarum
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