1.3.1.20: trans-1,2-dihydrobenzene-1,2-diol dehydrogenase
This is an abbreviated version!
For detailed information about trans-1,2-dihydrobenzene-1,2-diol dehydrogenase, go to the full flat file.
Word Map on EC 1.3.1.20
-
1.3.1.20
-
dihydrodiol
-
trans-dihydrodiols
-
medicine
-
polycyclic
-
catechols
-
nadp+-dependent
-
benzenedihydrodiol
-
indomethacin
-
penning
-
alpha-hydroxysteroids
-
o-quinones
-
talalay
-
anti-diol
-
1.1.1.184
-
+/-trans-7,8-dihydroxy-7,8-dihydrobenzoapyrene
-
non-k-region
-
benzaanthracene
-
alicyclic
-
trans-1,2-dihydrodiols
-
dicoumarol
-
chrysene
-
benzoapyrene-7,8-dione
-
harvey
-
pah-induced
-
androsterone
-
diagnostics
- 1.3.1.20
- dihydrodiol
-
trans-dihydrodiols
- medicine
-
polycyclic
- catechols
-
nadp+-dependent
- benzenedihydrodiol
- indomethacin
-
penning
-
alpha-hydroxysteroids
- o-quinones
-
talalay
-
anti-diol
-
1.1.1.184
-
+/-trans-7,8-dihydroxy-7,8-dihydrobenzoapyrene
-
non-k-region
-
benzaanthracene
-
alicyclic
-
trans-1,2-dihydrodiols
- dicoumarol
- chrysene
-
benzoapyrene-7,8-dione
-
harvey
-
pah-induced
- androsterone
- diagnostics
Reaction
Synonyms
AKR1C1, AKR1C2, DD, DDH, DDH1, DDH2, dehydrogenase, trans-1,2-dihydrobenzene-1,2-diol, DHDH, dihydrodiol dehydrogenase, More
ECTree
1.3.1.20 trans-1,2-dihydrobenzene-1,2-diol dehydrogenaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.3.1.20 - trans-1,2-dihydrobenzene-1,2-diol dehydrogenase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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
-
-
?
5beta-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5beta-pregnan-20-one + NADP+
-
-
-
-
?
camphorquinone + NADPH + H+
?
enzyme has dehydrogenase and reductase activities, enzyme is identical to NADP+-dependent D-xylose dehydrogenase
-
-
?
D-glucuronate + NADP+
D-glucurono-1,5-lactone + NADPH
-
isoform DD4 no activity
-
-
r
DL-glyceraldehyde + NADPH
?
-
probable identity with aldehyde reductase EC 1.1.1.2
-
-
?
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
-
-
?
glycolithocholic acid + NAD(P)+
3-oxo-glycocholanoic acid + NAD(P)H
-
NAD+ preferred as cofactor
-
-
?
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-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
?
(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+
?
-
DD4, wild-type and recombinant double mutant S145C/L311V
-
-
?
(S)-indan-1-ol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(S)-indan-1-ol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(S)-tetralol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(S)-tetralol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
1-acenaphthenol + NAD(P)+
?
recombinant: DD1, DD2, and 3alpha-hydroysteroid dehydrogenase/dihydrodiol dehydrogenase
-
-
?
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-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)+
-
reduces biologically important 3-oxo steroids of the androstane, pregnane, and cholane series
-
-
?
4-chromanol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
4-nitrobenzaldehyde + NAD(P)H
4-nitrobenzylalcohol + NAD(P)+
-
DD2, DD3
-
-
?
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
DD1, DD2, recombinant DD1
-
-
?
androsterone + NADPH
?
-
DD1, identical with 3alpha-hydroxysteroid dehydrogenase EC 1.1.1.50
-
-
?
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+
?
-
DD4, wild-type and recombinant double mutant S145C/L311V
-
-
?
D-arabinose + NADP+
D-arabinono-1,4-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+
-
only isoform DD3
-
-
?
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
D-glyceraldehyde + NADPH
?
-
DD2 and DD3 show high activity, DD4 only shows low activity
-
-
?
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+
-
also low activity with L-xylose
-
-
?
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+
-
also low activity with L-xylose
-
-
?
L-glyceraldehyde + NADPH
?
-
DD2 and DD3 show high activity, DD4 only shows low activity
-
-
?
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: specific for, no activity towards other alcohols, aldehydes, ketones and quinones
-
-
?
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
-
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
-
-
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
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
-
-
the enzyme transfers the 4-pro-R-hydrogen atom of NADPH to the carbonyl substrate
-
-
?
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
-
-
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
-
-
?
