Information on EC 1.3.1.20 - trans-1,2-dihydrobenzene-1,2-diol dehydrogenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.3.1.20
-
RECOMMENDED NAME
GeneOntology No.
trans-1,2-dihydrobenzene-1,2-diol dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dehydrogenation
oxidation
redox reaction
-
-
-
-
reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Metabolism of xenobiotics by cytochrome P450
-
-
SYSTEMATIC NAME
IUBMB Comments
trans-1,2-dihydrobenzene-1,2-diol:NADP+ oxidoreductase
-
CAS REGISTRY NUMBER
COMMENTARY hide
37255-32-6
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
3 forms: DD2 pI form 5.4, DD3 pI 5.0 form, and DD4 pI 4.2 form
-
-
Manually annotated by BRENDA team
rabbit
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-indan-1-ol + NADP+
?
show the reaction diagram
(R)-tetralol + NADP+
?
show the reaction diagram
(R)-tetralol + NADP+
? + NADPH
show the reaction diagram
(S)-(+)-1,2,3,4-tetrahydronaphth-1-ol + NADP+
? + NADPH
show the reaction diagram
(S)-indan-1-ol + NADP+
?
show the reaction diagram
(S)-indan-1-ol + NADP+
? + NADPH
show the reaction diagram
(S)-tetralol + NADP+
?
show the reaction diagram
(S)-tetralol + NADP+
? + NADPH
show the reaction diagram
1-acenaphthenol + NAD(P)+
?
show the reaction diagram
1-acenaphthol + NADP+
acenaphthylen-1-ol + NADPH
show the reaction diagram
-
-
-
-
?
1-indanol + NADP+
3H-inden-1-ol + NADPH
show the reaction diagram
17beta-estradiol + NAD(P)+
?
show the reaction diagram
2,3-heptanedione + NADPH
?
show the reaction diagram
-
-
-
-
?
2,3-hexanedione + NADPH
?
show the reaction diagram
2,3-pentanedione + NADPH
?
show the reaction diagram
2-cyclohexen-1-ol + NADP+
2-cyclohexene-1-one + NADPH
show the reaction diagram
-
NAD+
-
-
?
2-deoxy-D-glucose + NADP+
2-deoxy-D-glucono-1,5-lactone + NADPH + H+
show the reaction diagram
3-deoxyglucosone + NADPH
?
show the reaction diagram
-
-
-
-
?
3-keto steroid + NAD(P)H
3alpha-hydroxy steroid + NAD(P)+
show the reaction diagram
3-nitrobenzaldehyde + NADPH
3-nitrobenzylalcohol + NADP+
show the reaction diagram
-
-
-
-
?
3alpha-hydroxy steroid + NADP+
3-keto steroid + NADPH
show the reaction diagram
4-carboxybenzaldehyde + NADPH
?
show the reaction diagram
-
-
-
-
?
4-chromanol + NADP+
? + NADPH
show the reaction diagram
4-nitrobenzaldehyde + NAD(P)H
4-nitrobenzylalcohol + NAD(P)+
show the reaction diagram
5alpha-androstan-3,17-dione + NADPH
5alpha-androstan-3alpha-ol-17-one + NADP+
show the reaction diagram
-
isoform DD1, identical with 3alpha-hydroxysteroid dehydrogenase EC 1.1.1.50
-
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstan-3alpha,17beta-diol + NADP+
show the reaction diagram
5beta-androstan-3,17-dione + NADPH
5beta-androstan-3alpha-ol-17-one + NADP+
show the reaction diagram
5beta-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
show the reaction diagram
5beta-dihydrocortisone + NADPH
?
show the reaction diagram
-
-
-
-
?
5beta-pregnan-3,20-diol + NADP+
5beta-pregnan-20-ol-3-one + NADPH
show the reaction diagram
5beta-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5beta-pregnan-20-one + NADP+
show the reaction diagram
-
-
-
-
?
7alpha-hydroxy-5beta-cholestan-3-one + NADPH
?
show the reaction diagram
-
-
-
-
?
acenaphthenequinone + NADPH
?
show the reaction diagram
-
-
-
-
?
acetoin + NADP+
?
show the reaction diagram
-
-
-
-
?
alicyclic alcohol + NAD(P)+
?
show the reaction diagram
androsterone + NADPH
?
show the reaction diagram
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
show the reaction diagram
camphorquinone + NADPH
?
show the reaction diagram
-
-
-
-
?
camphorquinone + NADPH + H+
?
show the reaction diagram
enzyme has dehydrogenase and reductase activities, enzyme is identical to NADP+-dependent D-xylose dehydrogenase
-
-
?
chenodeoxycholic acid + NADP+
?
show the reaction diagram
-
DD1
-
-
?
cholic acid + NADP+
?
show the reaction diagram
cis-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
show the reaction diagram
D-arabinose + NADP+
D-arabinono-1,4-lactone + NADPH
show the reaction diagram
D-galactose + NADP+
D-galactono-1,5-lactone + NADPH
show the reaction diagram
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
show the reaction diagram
D-glucuronate + NADP+
D-glucurono-1,5-lactone + NADPH
show the reaction diagram
-
isoform DD4 no activity
-
-
r
D-glyceraldehyde + NADPH
?
show the reaction diagram
D-lactaldehyde + NADP+
?
show the reaction diagram
-
-
-
-
?
D-ribose + NADP+
?
show the reaction diagram
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
show the reaction diagram
deoxycholic acid + NADP+
?
show the reaction diagram
-
DD1
-
-
?
diacetyl + NADPH
?
show the reaction diagram
dihydroxyacetone + NADPH
?
show the reaction diagram
dihydroxyacetone phosphate + NADPH
?
show the reaction diagram
-
-
-
-
?
DL-glyceraldehyde + NADPH
?
show the reaction diagram
-
probable identity with aldehyde reductase EC 1.1.1.2
-
-
?
DL-glyceraldehyde-3-phosphate + NADPH
?
show the reaction diagram
-
-
-
-
?
epitestosterone + NAD(P)+
?
show the reaction diagram
-
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+
show the reaction diagram
-
-
-
-
?
glycolithocholic acid + NAD(P)+
3-oxo-glycocholanoic acid + NAD(P)H
show the reaction diagram
-
NAD+ preferred as cofactor
-
-
?
L-glyceraldehyde + NADPH
?
show the reaction diagram
L-lactaldehyde + NADP+
?
show the reaction diagram
-
-
-
-
?
lithocholic acid + NADP+
?
show the reaction diagram
methyl pyruvate + NADPH
methyl lactate + NADP+
show the reaction diagram
-
-
-
-
?
methylglyoxal + NADPH
?
show the reaction diagram
-
-
-
-
?
naphthalene dihydrodiol + NAD(P)+
?
show the reaction diagram
phenyl-1,2-propanedione + NADPH
?
show the reaction diagram
-
-
-
-
?
phenylglyoxal + NADPH
?
show the reaction diagram
-
-
-
-
?
pyridine-3-aldehyde + NADPH
?
show the reaction diagram
pyridine-4-aldehyde + NADPH
?
show the reaction diagram
-
-
-
-
?
S-(+)-1,2,3,4-tetrahydronaphth-1-ol + NADP+
? + NADPH
show the reaction diagram
succinic semialdehyde + NADPH
?
show the reaction diagram
-
isoform DD4 low activity
-
-
?
taurochenodeoxycholic acid + NADP+
?
show the reaction diagram
-
DD1, DD3
-
-
?
taurocholic acid + NADP+
?
show the reaction diagram
-
DD1
-
-
?
taurolithocholic acid + NADP+
?
show the reaction diagram
-
DD1, DD3
-
-
?
testosterone + NADPH + H+
4-androsten-3alpha,17beta-diol + NADP+
show the reaction diagram
-
NAD+
-
-
?
tetrahydrodeoxycorticosterone + NAD(P)+
?
show the reaction diagram
-
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
show the reaction diagram
trans-1,2-dihydroxy-1,2-dihydrophenanthrene + NADPH
?
show the reaction diagram
-
-
-
-
?
trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene + NADP+
benzo[a]-pyrene-7,8-dione + NADPH
show the reaction diagram
DD1, DD2, DD4, 3alpha-hydroxysteroid/dihydrodiol dehydrogenase
product is potent carcinogen
?
trans-benzene dihydrodiol + NADP+
? + NADPH
show the reaction diagram
trans-naphthalene dihydrodiol + NAD(P)+
?
show the reaction diagram
[1R,2R]-trans-cyclohexanediol + NADP+
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
5alpha-dihydrotestosterone + NADPH
5alpha-androstan-3alpha,17beta-diol + NADP+
show the reaction diagram
-
-
-
r
camphorquinone + NADPH + H+
?
show the reaction diagram
Q9TQS6
enzyme has dehydrogenase and reductase activities, enzyme is identical to NADP+-dependent D-xylose dehydrogenase
-
-
?
naphthalene dihydrodiol + NAD(P)+
?
show the reaction diagram
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NAD(P)+
NAD(P)H
-
high affinity for NADP(H)
NADPH
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
1,7-phenanthroline
DD1, recombinant DD1, but DD2 less sensitive
1-Indanone
-
recombinant DD4
17beta-estradiol
2,6-dihydroxyanthraquinone
3',3'',5',5''-tetrabromophenolphthalein
-
recombinant DD4
4-hydroxyacetophenone
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
-
-
androsterone
-
DD3
ascorbate
-
-
Barbital
Benzo[a]pyrene-7,8-dione
-
-
Betamethasone
Bromophenol blue
-
recombinant DD4
carboplatin
chenodeoxycholic acid
DD2 very sensitive, DD1 less sensitive, recombinant DD1
chenolithocholic acid
-
DD2
-
chrysin
inhibits enzyme expression at concentrations higher than 0.01 mM; inhibits enzyme expression at concentrations higher than 0.01 mM
Cibacron blue
-
-
cisplatin
cyclopentane-1,1-diacetic acid NaCl
-
inhibits only isoform F2
Dehydrolithocholic acid
-
DD2
dexamethasone
Dienstrol
-
-
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
Flufenamic acid
glutathione
-
wild-type and mutant C145S
Hexestrol
Ibuprofen
very sensitive: DD2, less sensitive: DD1, recombinant DD1
indomethacin
isoascorbic acid
KCl
-
increase in Km-value for D-xylose and NADP+
L-ascorbic acid
lithocholic acid
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
MgCl2
N-ethylmaleimide
-
wild-type and mutant C145S
naphthalene-1,2-dione
-
-
naproxen
-
DD2
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
phenolphthalein phosphate
-
recombinant DD4
Phosphate buffer
-
inhibitionn of mutant enzymes H79Q and Y180F
-
quercitrin
SO42-
-
inhibits only isoform F1
sorbinil
Stilbestrol
testosterone
-
-
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
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
bezafibric acid
-
DD4
Clofibric acid
-
DD4, CDD4-1
diphosphate
-
high concentration: F2 slight inhibition, F1 stimulation
fenofibric acid
-
DD4, CDD4-1
interleukin-6
stimulates enzyme expression; stimulates enzyme expression
potassium phosphate
-
-
SO42-
Sulfobromophthalein
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.056 - 0.382
(R)-tetralol
0.33
(S)-1-indanol
-
DD3
0.076 - 0.42
(S)-indan-1-ol
0.029 - 0.307
(S)-tetralol
0.022 - 0.54
1-Acenaphthenol
0.048 - 1.4
1-Indanol
3.9
2,3-Pentanedione
-
-
0.073 - 0.34
4-chromanol
3.3
4-Nitrobenzaldehyde
-
-
0.0031
5alpha-Androstan-3,17-dione
-
DD1
0.0029
5beta-androstan-3,17-dione
-
DD1
0.0074
5beta-Androstan-3alpha-ol-17-one
-
DD1
0.0035 - 0.0048
androsterone
0.1 - 26
Camphorquinone
0.0045
chenodeoxycholic acid
-
DD1
0.16
cholic acid
-
DD1
0.67 - 1.99
cis-benzene dihydrodiol
45
D-glyceraldehyde
-
-
0.8 - 213
D-xylose
0.0045
deoxycholic acid
-
DD1
0.8
diacetyl
-
2,3-butanedione
5.4
dihydroxyacetone
-
-
5
dihydroxyacetone phosphate
-
-
50
DL-glyceraldehyde-3-phosphate
-
-
121
L-Glyceraldehyde
-
-
0.0016 - 0.017
lithocholic acid
0.01 - 402
NADP+
0.001 - 28
NADPH
2.7 - 6.78
Naphthalene dihydrodiol
0.018 - 0.89
taurochenodeoxycholic acid
0.21
taurocholic acid
-
DD1
0.0038 - 0.033
taurolithocholic acid
0.017 - 2.6
trans-benzene dihydrodiol
0.28
trans-benzenedihydrodiol
-
-
1.5
trans-naphthalenedihydrodiol
-
DD3
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
84 - 2520
(R)-tetralol
0.417
(S)-1-indanol
Bos taurus
-
DD3
0.0567 - 2040
(S)-indan-1-ol
1320 - 2160
(S)-tetralol
0.125 - 2
1-Acenaphthenol
150 - 2880
4-chromanol
11.3
4-Nitrobenzaldehyde
Macaca fuscata
-
-
0.045 - 0.108
5beta-Androstan-3alpha,17beta-diol
0.00667 - 0.0183
androsterone
0.004 - 62.5
Camphorquinone
0.0115
chenodeoxycholic acid
Bos taurus
-
DD1
0.045 - 0.233
cholic acid
31.4
D-glyceraldehyde
Macaca fuscata
-
-
2.6
D-xylose
Macaca fuscata
-
wild type enzyme, in 25 mM Tris-HCl pH 7.5, at 25C
0.133
deoxycholic acid
Bos taurus
-
DD1
5.5
dihydroxyacetone
Macaca fuscata
-
-
4.3
dihydroxyacetone phosphate
Macaca fuscata
-
-
8
DL-glyceraldehyde-3-phosphate
Macaca fuscata
-
-
9.1
L-Glyceraldehyde
Macaca fuscata
-
-
0.0065 - 0.0867
lithocholic acid
0.367 - 0.783
taurochenodeoxycholic acid
0.07
taurocholic acid
Bos taurus
-
DD1
0.0817 - 0.217
taurolithocholic acid
0.00667 - 90
trans-benzene dihydrodiol
0.65 - 34
trans-naphthalene dihydrodiol
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.15
1-Indanone
-
recombinant DD4
0.011
5alpha-Androstan-3,17-dione
-
DD3
0.041
5beta-androstan-3,17-dione
-
DD3
0.031
5beta-Androstan-3alpha-ol-17-one
-
DD3
0.006
androsterone
-
DD3
0.0003
chenolithocholic acid
-
DD2
-
0.00009
Dehydrolithocholic acid
-
DD2
0.0006
Flufenamic acid
-
DD2
0.076
indomethacin
-
DD2
0.00004
lithocholic acid
-
DD2
0.0011
naproxen
-
DD2
0.00008
Phenolphthalein
-
recombinant DD4
0.00006
ursodeoxylithocholic acid
-
DD2
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00097 - 0.136
4-hydroxyacetophenone
0.037 - 4.176
isoascorbic acid
0.45
L-ascorbic acid
Sus scrofa
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0067
-
pH 7.4, cytosolic fraction of parental 2008 cell
0.011
-
extract, substrate naphthalene dihydrodiol
0.0213
-
pH 7.4, cytosolic fraction of 2008 cell expressing isoform 2
0.024
-
extract, substrate naphthalene dihydrodiol
0.0263
-
pH 7.4, cytosolic fraction of 2008 cell expressing isoform 1
0.0328
-
pH 7.4, cytosolic fraction of 2008/C13* cell
0.038
-
extract, substrate naphthalene dihydrodiol
0.04
-
R148A and R202A mutant, 25 mM Tris-HCl, pH 7.5, 0.25 mM NADP+
0.05
-
wild type enzyme in dimeric form, 25 mM Tris-HCl, pH 7.5, 0.25 mM NADP+
0.11 - 0.12
-
pH 10.0, kidney cortex, substrate trans-benzene dihydrodiol
0.21
DD4, substrate androsterone
0.73
-
DD4 recombinant double mutant S145C/L311V, purified, substrate (S)-indan-1-ol
1.2
-
monomeric form
1.5
-
DD4 recombinant mutant S145C, purified, substrate (S)-indan-1-ol
2.1
recombinant DD1, substrate 1-acenaphthenol
2.23
-
recombinant DD4, substrate (S)-indan-1-ol
2.5
recombinant DD2, substrate 1-acenaphthenol
2.8
recombinant 3alpha-hydroxysteroid/dihydrodiol dehydrogenase
5.525
-
purified enzyme
5.65
-
purified enzyme
7.3
-
co-purified enzyme, D-xylose dehydrogenase activity
8
-
co-purified enzyme, dihydrodiol dehydrogenase activity
500
-
substrate 1-indanol, 2008 cells
2000
-
substrate 1-indanol, 2008 cells constitutively overexpressing enzyme
6000
-
substrate 1-indanol, 2008/C13* cells
7000
-
substrate 1-acenaphthol, 2008 cells
26000
-
substrate 1-acenaphthol, 2008 cells constitutively overexpressing enzyme
33000
-
substrate 1-acenaphthol, 2008/C13* cells
35000
-
substrate camphorquinone, 2008 cells
65000
-
substrate camphorquinone, 2008/C13* cells
71000
-
substrate camphorquinone, 2008 cells constitutively overexpressing enzyme
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.8
-
F2: reduction of vicinal diketones, aromatic aldehydes and glyceraldehydes + NAD(P)H
6 - 8
-
F1: reduction of vicinal diketones, aromatic aldehydes and glyceraldehydes + NADPH
7.6
-
F2: oxidation of naphthalene dihydrodiol + NAD(P)+
9 - 9.5
-
DD2
9.7 - 10.5
-
mutant K84N of DD3
9.8
-
trans-benzene dihydrodiol
10
-
mutant D50N of DD3
10.2
-
F1: oxidation of trans-dihydrodiols of naphthalene and benzene + NADP+
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
assay at, substrate D-xylose, pH 10.0
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
squamous cell carcinoma
Manually annotated by BRENDA team
-
tumor from patients with gastric cancer
Manually annotated by BRENDA team
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low activity
Manually annotated by BRENDA team
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lung cancer cell line, high expression of enzyme isoform DDH1 and enzyme CYP1A1, and high level of DNA-benzo[a]pyrene adducts
Manually annotated by BRENDA team
-
lung cancer cell line, high expression of enzyme isoform DDH1 and enzyme CYP1A1, and high level of DNA-benzo[a]pyrene adducts
Manually annotated by BRENDA team
-
lung adenocarcinoma cell line
Manually annotated by BRENDA team
-
lung adenocarcinoma cell line
Manually annotated by BRENDA team
-
lung adenocarcinoma cell line
Manually annotated by BRENDA team
-
lung adenocarcinoma cell line
Manually annotated by BRENDA team
-
lung adenocarcinoma cell line
Manually annotated by BRENDA team
-
lung adenocarcinoma cell line
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
additional information
not found in liver and kidney
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
32000
-
1 * 32000, DD3, and 1 * 36000, DD4, SDS-PAGE
33000
-
2 * 33000 (DD3), 2 * 35000 (DD4), SDS-PAGE
64000
-
DD3, gel filtration
68000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
additional information
-
the dissociation of DD into the monomer largely affects the stability rather than catalytic activity
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystals are obtained at 19.9C in a culture plate via the vapour-diffusion method, crystal structure of dimeric dihydrodiol dehydrogenase complexed with the inhibitor isoascorbic acid is determined at 2.59 A resolution
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dimeric apoenzyme (at 2.0 A resolution) and enzyme-inhibitor complex (at 2.9 A resolution), crystals are grown using droplets consisting of the dihydrodiol dehydrogenase/NADPH solution mixed with a matching volume containing 1.5 M ammonium phosphate and 0.1 M sodium citrate at pH 5.6, tertiary structure is formed by a classical dinucleotide binding fold comprising of 2 beta-alpha-beta-alpha-beta motifs at the N-terminus and an eight-stranded, predominantly antiparallel beta-sheet at the C-terminus
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vapour diffusion method with 2 M ammonium phosphate and 0.1 M sodium citrate buffer (pH 5.6) and 20% glycerol
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in complex with isoascorbic acid, vapour diffusion method with 2 M ammonium sulfate, 0.1 M sodium citrate buffer pH 5.0, at 20C
-
vapour diffusion at 295 K with NADPH, growth for 2 days, buffer A: 1.5 M ammoinum phosphate, 0.1 M sodium citrate, pH 5.6 + buffer B: 10 mM Tris-HCl, 2 mM 2-mercaptoethanol, pH 8.5, preliminary x-ray structure analysis
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complexed with NADP+ and testosterone, 10fold molar excess of NADP+, 'waterbug' dialysis method in 10 mM potassium phosphate buffer, pH 7.0, containing 1 mM EDTA, 1 mM 2-mrcapthoethanol, 5% acetonitrile and 0.2 mM testosterone, and crystallization in presence of polethylene glycol 8000 in hanging drops at room temperature, single crystals; cryocrystallization: crystals were soaked in 21% polyethylene glycol 8000, 0.1 M sodium cacodylate, pH 6.4, 1.25 mM NADP+, 0.1 mM testosterone and 15% 2-methyl-2,4-pentanediol as cryoprotectant; structure determination, cofactor and substrate binding site, and model building
-
vapour diffusion at 22C in 100 mM sodium citrate, polyethylene glycol 6000 25%, 120 mM ammonium sulfate, pH 5.8, x-ray analysis
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45
-
dihydrodiol dehydrogenase and 3(17)alpha-hydroxysteroid dehydrogenase activity, pH 7.5, 5 min
50
-
dihydrodiol dehydrogenase and 3(17)alpha-hydroxysteroid dehydrogenase activity, pH 7.5, all activity lost
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate precipitation, Red Sepharose column chromatography, and Sephadex G-100 gel filtration
-
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
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co-purification of dihydrodiol and D-xylose dehydrogenase activities indicating that EC 1.1.1.179 and EC 1.3.1.20 are the same enzyme
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DD1 and DD3
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DD1, DD2, DD3, DD4
-
DD1, DD2, DD4 and 3alpha-hydroxysteroid dehydrogenase/dehydrodiol dehydrogenase, all recombinant from Escherichia coli
DD1, DD4, CDD1-4, CDD4-1, all recombinant from Escherichia coli
-
DD1, recombinant from Escherichia coli
DD3, recombinant, His-tagged protein from Escherichia coli
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DD4 double mutant S145C/L311V recombinant from Escherichia coli
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dihydrodiol dehydrogenase EC 1.3.1.20 and 3(17)alpha-hydroxysteroid dehydrogenase EC 1.1.1.59 activities reside on a single protein; enzyme forms: DD1, DD3
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purified from microsomes
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recombinant enzymes are purified from the 12000g supernatants of the homogenates of the cells, the single mutant enzymes are partially purified by the ammonium sulphate fractionation and chromatography on a Sephadex G-100 column, the wild type and double mutant enzyme are further purified by chromatography on a Red Sepharose column
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the recombinant enzymes are purified from the 12000g supernatants of the homogenates of the cells
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wild-type and mutant protein recombinant from Escherichia coli
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DD1, DD2, DD4, type 2 3alpha-hydroxysteroid/dihydrodiol dehydrogenase, expression in Escherichia coli
DD1, DD4, CDD1-4, CDD4-1, all expressed in Escherichia coli
-
DD1, expression in Escherichia coli
DD4 double mutant S145C/L311V overexpressed in Escherichia coli; DD4, isolation of mRNA of native mutants isolated from a liver sample, synthesis of cDNA by RT-PCR, polymorphism of DD4 gene
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DD4, expression in Escherichia coli JM109
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expressed in Escherichia coli BL21 (DE3) cells
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expressed in Escherichia coli BL21(DE3) cells
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expression in Escherichia coli
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expression of His-tagged protein in Escherichia coli
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expression of wild-type and mutants, H79Q and Y180F, in Escherichia coli
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in Escherichia coli BL21(DE3)
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overexpression in Escherichia coli
-
wild-type protein and mutants are expressed in Escherichia coli BL21 (DE3)
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
C87S
-
DD1 mutant
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
Q172L
-
DD1 mutant
R170H
-
DD1 mutant
R47H
-
DD1 mutant
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
T38V
-
DD1 mutant
V151M
-
DD1 mutant
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
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production by site-directed mutagenesis
K97M