Information on EC 1.1.1.159 - 7alpha-hydroxysteroid dehydrogenase

Word Map on EC 1.1.1.159
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)

The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.159
-
RECOMMENDED NAME
GeneOntology No.
7alpha-hydroxysteroid dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
cholate + NAD+ = 3alpha,12alpha-dihydroxy-7-oxo-5beta-cholan-24-oate + NADH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
glycocholate metabolism (bacteria)
-
-
Secondary bile acid biosynthesis
-
-
ursodeoxycholate biosynthesis (bacteria)
-
-
SYSTEMATIC NAME
IUBMB Comments
7alpha-hydroxysteroid:NAD+ 7-oxidoreductase
Catalyses the oxidation of the 7alpha-hydroxy group of bile acids and alcohols both in their free and conjugated forms. The Bacteroides fragilis and Clostridium enzymes can also utilize NADP+.
CAS REGISTRY NUMBER
COMMENTARY hide
39361-64-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
ATCC25285
-
-
Manually annotated by BRENDA team
formerly Eubacterium sp. strain VP1
-
-
Manually annotated by BRENDA team
strain VPI 12708
-
-
Manually annotated by BRENDA team
strain VPI 12708
-
-
Manually annotated by BRENDA team
strain B-0831
-
-
Manually annotated by BRENDA team
strain B-0831
-
-
Manually annotated by BRENDA team
strain CBS 897.97
-
-
Manually annotated by BRENDA team
strain CBS 897.97
-
-
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
(3alpha,5beta)-3-hydroxy-7,12-dioxocholan-24-oic acid + NADH
(3alpha,5beta,7alpha)-3,7-dihydroxy-12-oxocholan-24-oic acid + NAD+
show the reaction diagram
-
-
-
-
r
12-ketochenodeoxycholic acid + NAD+
7,12-diketochenodeoxycholic acid + NADH
show the reaction diagram
3,7-diketocholic acid + NADH
3-ketocholic acid + NAD+
show the reaction diagram
-
high activity
-
-
r
6-fluoro-7-ketohyocholic acid + NADH
6-fluoro-3alpha,6alpha,7alpha-trihydroxy-5beta-cholan-24-oic acid + NAD+ + NAD+
show the reaction diagram
-
-
-
-
r
7,12-diketolithocholic acid + NADH
12-ketochenodeoxycholic acid + NAD+
show the reaction diagram
-
-
-
r
7-keto-lithocholic acid + NADH
cheno-deoxycholic acid + NAD+
show the reaction diagram
7-ketochenodeoxycholic acid + NADH
3alpha,7alpha-dihydroxy-5beta-cholanoic acid + NAD+
show the reaction diagram
-
-
-
-
r
7-ketohyocholic acid + NADH
3alpha,6alpha,7alpha-trihydroxy-5beta-cholan-24-oic acid + NAD+
show the reaction diagram
-
low activity
-
-
r
bile acids + NAD(P)+
?
show the reaction diagram
chenodeoxycholic acid + NAD(P)+
3alpha-hydroxy-7-oxo-5beta-cholan-24-oic acid + NAD(P)H
show the reaction diagram
chenodeoxycholic acid + NAD+
3alpha-hydroxy-7-oxo-5beta-cholan-24-oic acid + NADH
show the reaction diagram
cholic acid + NAD(P)+
3alpha,12alpha-dihydroxy-7-oxo-5beta-cholan-24-oic acid + NADH
show the reaction diagram
cholic acid + NAD+
3alpha,12alpha-dihydroxy-7-oxo-5beta-cholan-24-oic acid + NADH
show the reaction diagram
cholic acid + NADH
7-ketocholic acid + NAD+
show the reaction diagram
-
low activity in the reverse reaction
-
-
r
dehydrocholic acid + NADH
3,12-diketolithocholic acid + NAD+
show the reaction diagram
-
-
-
r
ethyl (R)-2-hydroxy-2-(3,5-difluorophenyl)acetate + NAD+
ethyl 2-oxo-2-(3,5-difluorophenyl)acetate + NADH
show the reaction diagram
-
-
-
-
?
ethyl (R)-2-hydroxy-3,3-dimethylbutyrate + NAD+
ethyl 2-oxo-3,3-dimethylbutyrate + NADH
show the reaction diagram
-
-
-
-
?
ethyl (R)-2-hydroxy-3-methylbutyrate + NAD+
ethyl 2-oxo-3-methylbutyrate + NADH
show the reaction diagram
-
-
-
-
?
ethyl 2-hydroxy-2-(3,4-dichlorophenyl)acetate + NAD+
ethyl 2-oxo-2-(3,4-dichlorophenyl)acetate + NADH
show the reaction diagram
-
-
-
-
?
ethyl 2-hydroxy-2-(4-bromophenyl)acetate + NAD+
ethyl 2-oxo-2-(4-bromophenyl)acetate + NADH
show the reaction diagram
-
-
-
-
?
ethyl 2-hydroxy-2-(4-chlorophenyl)acetate + NAD+
ethyl 2-oxo-2-(4-chlorophenyl)acetate + NADH
show the reaction diagram
-
-
-
-
?
ethyl 2-hydroxy-2-(4-cyanophenyl)acetate + NAD+
ethyl 2-oxo-2-(4-cyanophenyl)acetate + NADH
show the reaction diagram
-
high activity
-
-
?
ethyl 2-hydroxy-2-(4-fluorophenyl)acetate + NAD+
ethyl 2-oxo-2-(4-fluorophenyl)acetate + NADH
show the reaction diagram
-
-
-
-
?
ethyl 2-hydroxy-2-(4-methylphenyl)acetate + NAD+
ethyl 2-oxo-2-(4-methylphenyl)acetate + NADH
show the reaction diagram
-
-
-
-
?
ethyl 2-hydroxy-2-cyclohexylacetate + NAD+
ethyl 2-oxo-2-cyclohexylacetate + NADH
show the reaction diagram
-
best substrate
-
-
?
ethyl 2-hydroxy-2-phenylacetate + NAD+
ethyl 2-oxo-2-phenylacetate + NADH
show the reaction diagram
-
-
-
-
?
glycochenodeoxycholic acid + NAD(P)+
N-[3alpha-hydroxy-7,24-dioxocholan-24-yl]glycine + NAD(P)H
show the reaction diagram
glycocholic acid + NAD+
N-[3alpha,12alpha-dihydroxy-7,24-dioxo-5beta-cholan-24-yl]glycine + NADH
show the reaction diagram
methyl 2-hydroxy-2-phenylacetate + NAD+
methyl 2-oxo-2-phenylacetate + NADH
show the reaction diagram
-
-
-
-
?
methyl benzoylformate + NADH
?
show the reaction diagram
-
-
-
-
?
taurochenodeoxycholic acid + NAD+
2[[3alpha-hydroxy-7,24-dioxo-5beta-cholan-24-yl]amino]ethane sulfonic acid + NADH
show the reaction diagram
taurocholic acid + NAD+
2[[3alpha,12alpha-dihydroxy-7,24-dioxo-5beta-cholan-24-yl]amino]ethane sulfonic acid + NADH
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
7-keto-lithocholic acid + NADH
cheno-deoxycholic acid + NAD+
show the reaction diagram
-
in the gastrointestinal tract of host organisms
-
-
?
bile acids + NAD(P)+
?
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
thio-NAD+
-
utilized with the same activity as NAD+
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
CaCl2
-
activation
KCl
-
activation
Mg2+
-
activation
NaCl
-
activation
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
-
-
ascorbic acid
-
-
chenodeoxycholate
-
substrate inhibition at concentration above 1 mM
CoCl2
CuCl2
diethyl dicarbonate
-
complete
FeCl3
glycochenodeoxycholate
-
substrate inhibition at concentration above 1 mM
HgCl2
iodoacetic acid
-
70% remaining activity at concentration 1 mM
N-bromosuccinimide
-
complete
o-phenanthroline
-
70% remaining acitvity at concentration 1 mM
p-chloromercuribenzoate
-
80% remaining activity at concentration 0.3 mM
p-hydroxymercuribenzoate
complete inhibition at 0.0075 mM
potassium oxalate
-
-
Sodium citrate
-
-
sodium lauryl sulfate
-
-
Sodium perchlorate
-
-
Sodium periodate
-
-
Sodium persulfate
-
-
taurochenodeoxycholate
-
substrate inhibition at concentration above 1 mM
Triton X-100
-
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
-
activation
dithiothreitol
-
activation
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.38
12-ketolithocholic acid
-
-
0.32 - 0.34
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoic acid
-
-
0.32 - 0.34
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl glycine
-
-
0.32 - 0.34
3alpha,7alpha,12alpha-trihydroxycholanoyl taurine
-
-
0.1
3alpha,7alpha-dihydroxy-5beta-cholanoic acid
-
-
0.1
3alpha,7alpha-Dihydroxy-5beta-cholanoyl glycine
-
-
0.1
3alpha,7alpha-dihydroxy-5beta-cholanoyl taurine
-
-
0.99
7,12-Diketolithocholic acid
-
-
0.0065 - 0.43
chenodeoxycholic acid
0.09 - 1.2
cholic acid
0.7
Dehydrocholic acid
-
-
0.085
glycochenodeoxycholic acid
-
-
1 - 1.25
glycocholic acid
0.15 - 0.709
NAD+
0.25 - 1.3
NADH
0.19 - 0.24
taurochenodeoxycholic acid
1 - 2
taurocholic acid
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8.18
chenodeoxycholic acid
Escherichia coli
-
-
7.92 - 151
cholic acid
0.417
glycocholic acid
Escherichia coli
-
-
3.43
taurochenodeoxycholic acid
Escherichia coli
-
-
3.13
taurocholic acid
Escherichia coli
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.035
-
cell extract
0.11
-
purified enzyme
0.32
-
purified recombinant enzyme, substrate methyl benzoylformate
1.1
-
crude extract
45
-
deoxycholic acid or lithocholic acid
70
-
purified native enzyme
332
-
NADP+, recombinant enzyme from Escherichia coli
351
purified enzyme, 37°C
374
-
NADP+
400
-
7,12-diketolithocholic acid, NADH
1600
-
cholic acid, NAD+
1700
-
12-ketolithocholic acid, NAD+
2348
-
taurocholic acid
2900
-
dehydrocholic acid, NADH
2916
-
glycocholic acid
3486
-
cholic acid
3743
-
taurochenodeoxycholic acid
3856
-
glycochenodeoxycholic acid
4164
-
chenodeoxycholic acid
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.3
-
dehydrocholic acid reduction
6.5
NADH oxidation
7 - 9
-
NADP+-dependent activity
8.5 - 9
-
oxidation of 7alpha-hydroxy group
9 - 10
-
oxidation of cholic acid
9.4 - 9.6
-
-
9.5 - 10
-
NAD+-dependent activity
10
-
oxidation of cholic acid
10.5
-
oxidation of cholic acid
additional information
-
value for reduction of dehydrocholic acid below 5.2, not measurable due to insolubility of substrate
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 10.5
NAD reduction
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22
-
assay at room temperature
28
-
substrate cholic acid
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Brucella melitensis biotype 1 (strain 16M / ATCC 23456 / NCTC 10094)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25000
-
SDS-PAGE
27000
-
4 * 27000, SDS-PAGE
28000
-
4 * 28000, SDS-PAGE
30000
-
? * 30000, SDS-PAGE
54000
-
gel filtration
80000
-
NAD+-specific form, gel filtration
104000
-
gel filtration
107100
-
sequence determination
108000
-
gel filtration
110000
120000
-
gel filtration
127000
-
NADP+-dependent form, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
? * 30000, SDS-PAGE
tetramer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
binary complex with NAD+, ternary complex with NADH and 7-oxoglycochenodeoxycholic acid as product, as well as possibly partially glycochenodeoxycholic acid as substrat
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.7 - 10.5
-
5°C overnight
286075
6 - 11
-
-
286075
8 - 9
-
-
286085
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
stable below
40
-
inactivation at
60
-
10 min stable
75
-
30 min, presence of substrates, NAD+-dependent form stable
80
-
10 min, complete inactivation
additional information
-
the enzyme is thermostable
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
inactivation by freezing
-
NAD+-dependent form lyophilized is stable to freezing/thawing, NADP+-dependent form lyophilized is unstable
-
stabilization by glutathione, EDTA
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, 7 days
-
4°C, purified enzyme, 50 mM sodium phosphate, pH 7.5, stable for 2 days
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme 175fold by anion exchange chromatography, ammonium sulfate fractionation, hydrophobic interaction and affinity chromatography
-
partially purified by ion-exchange chromatography
-
recombinant enzyme from Escherichia coli by heat treatment at 55-60°C, polyethyleneimine treatment, ammonium sulfate fractionation, and gel filtration, followed by lyophilization
-
recombinant from Escherichia coli, high yield
-
wild-type and recombinant from Escherichia coli
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
expression in Escherichia coli DH5alpha-MCR, DNA and amino acid sequence analysis
-
gene from strain HB101 cloned in plasmid pSD1 and expressed in Escherichia coli strain DH1
-
overexpression in Escherichia coli
-
overexpression in Escherichia coli DH5alpha, amino acid sequence analysis and comparison with other dehydrogenases
-
site directed mutagenesis
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
K163I
-
5.25% activity of wild-type activity
K163R
-
63.7% activity of wild-type activity
S146A
-
20.3% activity of wild-type activity
S146H
-
35.6% activity of wild-type activity
Y159F
-
no activity
Y159H
-
13.3% activity of wild-type activity
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
-
assay for stereospecific labeling of coenzymes NADP+ and NADPH
degradation
-
new integrated chemo-enzymatic synthesis of ursodeoxycholic acid starting from sodium cholate by 7alpha- and 12alpha-hydroxysteroid dehydrogenases
synthesis
Show AA Sequence (659 entries)
Please use the Sequence Search for a specific query.