Information on EC 1.1.1.176 - 12alpha-hydroxysteroid dehydrogenase

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The expected taxonomic range for this enzyme is: Bacteria

EC NUMBER
COMMENTARY
1.1.1.176
-
RECOMMENDED NAME
GeneOntology No.
12alpha-hydroxysteroid dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
cholate + NADP+ = 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oate + NADPH + H+
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
redox reaction
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
glycocholate metabolism (bacteria)
-
SYSTEMATIC NAME
IUBMB Comments
12alpha-hydroxysteroid:NADP+ 12-oxidoreductase
Catalyses the oxidation of the 12alpha-hydroxy group of bile acids, both in their free and conjugated form. Also acts on bile alcohols.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
12alpha-HSDH
-
-
12alpha-HSDH
-
-
12alpha-hydroxy steroid dehydrogenase
-
-
-
-
dehydrogenase, 12alpha-hydroxy steroid
-
-
-
-
NAD-dependent 12alpha-hydroxysteroid dehydrogenase
-
-
-
-
NADP-12alpha-hydroxysteroid dehydrogenase
-
-
-
-
NADP-dependent 12alpha-hydroxysteroid dehydrogenase
-
-
CAS REGISTRY NUMBER
COMMENTARY
61642-40-8
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
group P, strain 48-50
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
12-ketochenodeoxycholic acid + NADH
cholic acid + NAD+
show the reaction diagram
-
-
-
r
12-oxochenodeoxycholic acid + NADP+
(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxycholan-24-oic acid + NADPH + H+
show the reaction diagram
-
-
-
-
?
7alpha,12alpha-dihydroxy-5beta-cholanoate + NAD+
7alpha-hydroxy-12-oxo-5beta-cholanoate + NADH
show the reaction diagram
-
-
-
-
?
allocholate + NAD+
3alpha,7alpha-dihydroxy-12-oxo-5alpha-cholan-24-oic acid + NADH
show the reaction diagram
-
-
-
-
?
allodeoxycholate + NAD+
3alpha-hydroxy-12-oxo-5alpha-cholan-24-oic acid + NADH
show the reaction diagram
-
-
-
-
?
cholic acid + NAD(P)+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H
show the reaction diagram
-
-
-
-
?
cholic acid + NAD(P)+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H
show the reaction diagram
-
-
-
?
cholic acid + NAD(P)+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H
show the reaction diagram
-
-
-
-
r
cholic acid + NAD(P)+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H
show the reaction diagram
-
-
-
-
?
cholic acid + NAD(P)+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H
show the reaction diagram
-
-
-
-
?
cholic acid + NAD(P)+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H
show the reaction diagram
-
hardly accepts N6-modified NADP+ derivative
-
-
?, r
cholic acid + NAD(P)+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H
show the reaction diagram
-
i.e. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oic acid
-
-
?, r
cholic acid + NADP+
12-ketochenodeoxycholic acid + NADPH
show the reaction diagram
-
the assay is performed using an NADP+-regenerating system with acetone, NADPH, 2-propanol and alcohol dehydrogenase from Lactobacillus brevis or Thermoanaerobium brockii, overview
-
-
r
deoxycholic acid + NAD(P)+
3alpha-hydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H + H+
show the reaction diagram
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid
-
-
?
deoxycholic acid + NAD(P)+
3alpha-hydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H + H+
show the reaction diagram
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid
-
-
?
deoxycholic acid + NAD(P)+
3alpha-hydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H + H+
show the reaction diagram
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid
-
-
?
deoxycholic acid + NAD(P)+
3alpha-hydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H + H+
show the reaction diagram
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid
-
-
r
deoxycholic acid + NAD(P)+
3alpha-hydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H + H+
show the reaction diagram
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid
-
-
?
deoxycholic acid + NAD(P)+
3alpha-hydroxy-12-oxo-5beta-cholan-24-oic acid + NAD(P)H + H+
show the reaction diagram
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid
-
-
?
deoxycholic acid + NAD+
3alpha-hydroxy-12-oxo-5beta-cholan-24-oic acid + NADH + H+
show the reaction diagram
-
-
-
-
?
glycocholic acid + NAD+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanoyl glycine + NADH
show the reaction diagram
-
i.e. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl glycine
-
-
?
glycocholic acid + NAD+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanoyl glycine + NADH
show the reaction diagram
-
i.e. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl glycine
-
-
?
glycocholic acid + NAD+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanoyl glycine + NADH
show the reaction diagram
-
i.e. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl glycine
-
-
?
glycocholic acid + NAD+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanoyl glycine + NADH
show the reaction diagram
-
i.e. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl glycine
-
-
?
glycodeoxycholic acid + NAD+
3alpha-hydroxy-12-oxo-5beta-cholanoyl glycine + NADH
show the reaction diagram
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholanoyl glycine
-
-
?
glycodeoxycholic acid + NAD+
3alpha-hydroxy-12-oxo-5beta-cholanoyl glycine + NADH
show the reaction diagram
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholanoyl glycine
-
-
?
glycodeoxycholic acid + NAD+
3alpha-hydroxy-12-oxo-5beta-cholanoyl glycine + NADH
show the reaction diagram
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholanoyl glycine
-
-
?
glycodeoxycholic acid + NAD+
3alpha-hydroxy-12-oxo-5beta-cholanoyl glycine + NADH
show the reaction diagram
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholanoyl glycine
-
-
?
taurocholic acid + NAD(P)+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanoyl taurine + NAD(P)H
show the reaction diagram
-
-
-
-
-
taurocholic acid + NAD(P)+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanoyl taurine + NAD(P)H
show the reaction diagram
-
i.e. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl taurine
-
-
?
taurocholic acid + NAD(P)+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanoyl taurine + NAD(P)H
show the reaction diagram
-
i.e. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl taurine
-
-
?
taurocholic acid + NAD(P)+
3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanoyl taurine + NAD(P)H
show the reaction diagram
-
i.e. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl taurine
-
-
?
taurodeoxycholic acid + NAD+
3alpha-hydroxy-12-oxo-5beta-cholanoyl taurine + NADH
show the reaction diagram
-
-
-
-
?
taurodeoxycholic acid + NAD+
3alpha-hydroxy-12-oxo-5beta-cholanoyl taurine + NADH
show the reaction diagram
-
-
-
-
?
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
12-ketochenodeoxycholic acid + NADH
cholic acid + NAD+
show the reaction diagram
-
-
-
r
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
NAD+
-
10% of NADP+-activity
NADP+
-
low activity
NADPH
-
B-stereospecific
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
acetone
-
at 25% v/v and above
p-chloromercuribenzoate
-
-
pyridoxal 5'-phosphate
-
protection by NADP+ or NADPH
additional information
-
no substrate inhibition at high concentration of cholic acid
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0012
-
12-oxochenodeoxycholic acid
-
-
0.028
-
3alpha,12alpha-dihydroxy-5beta-cholanoate
-
-
0.8
-
3alpha,12alpha-dihydroxy-5beta-cholanoate
-
-
1.6
-
3alpha,12alpha-dihydroxy-5beta-cholanoate
-
-
0.17
-
3alpha,12alpha-dihydroxy-5beta-cholanoyl glycine
-
-
0.57
-
3alpha,12alpha-dihydroxy-5beta-cholanoyl glycine
-
-
0.44
-
3alpha,12alpha-dihydroxy-5beta-cholanoyl taurine
-
-
0.059
-
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoate
-
-
7
-
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoate
-
-
0.25
-
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl glycine
-
-
2.7
-
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl glycine
-
-
0.03
-
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl methyl ester
-
3alpha,12alpha-dihydroxy-5beta-cholanoate
4
-
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl taurine
-
-
0.1
-
7alpha,12alpha-dihydroxy-5beta-cholanoate
-
-
0.072
-
cholic acid
-
-
0.045
-
deoxycholic acid
-
-
0.024
-
NAD+
-
-
0.035
-
NADP+
-
-
0.0085
-
NADPH
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0.027
-
-
cell extract
0.3
-
-
purified enzyme
additional information
-
-
assay method development using an NADP+-regenerating system with acetone, NADPH, 2-propanol and alcohol dehydrogenase from Lactobacillus brevis or Thermoanaerobium brockii, optimization, overview
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5
6
-
reduction of dehydrocholic acid
8
10.5
-
oxidation of cholic acid
8.5
10.5
-
oxidation of bile acids
8.5
9
-
oxidation of cholic acid
8.5
9.5
-
oxidation of cholic acid
10.5
-
-
oxidation of bile acids
10.5
-
-
oxidation of deoxycholic acid
additional information
-
-
reduction of 12-oxochenodeoxycholic acid optimal below pH 5.0, not measurable due to insolubility of substrate
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
-
optimum above 55C, not measurable because enzyme is inactivated above 55C
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-
enzyme in 50% glycerol-containing solution
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
98000
106000
-
native PAGE, analytical ultracentrifugation
102000
108000
-
native PAGE, analytical ultracentrifugation, FPLC gel filtration
110000
-
-
SDS-PAGE, gel filtration
125000
-
-
gel filtration
225000
-
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
dimer
-
1 * 58000 + 1* 64000, SDS-PAGE
tetramer
-
4 * 26000, no disulfide bonds, SDS-PAGE, electron microscopy; 4 * 26000, SDS-PAGE
TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0
4
-
half-life: 11 days
25
-
-
half-life: 4 days, increases to 10 days by addition of NADP+
30
-
-
half-life: 2 days, increases to 5 days by addition of NADP+
43
-
-
slow inactivation
50
-
-
30 min, inactivation
56
-
-
rapid inactivation
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
glycerol, 50% v/v, stabilization
-
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
4C, 0.5 ml TEA-buffer, 3 days
-
-20C, 20 days, 50% loss of activity
-
-30C, 6 months, 50% glycerol, no loss of activity
-
-30C, concentrated form, at least 6 months
-
-20C, 3 months, 5% loss of activity
-
-20C, lyophilized, 4 months
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
partially purified by ion-exchange chromatography
-
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
degradation
-
new integrated chemo-enzymatic synthesis of ursodeoxycholic acid starting from sodium cholate by 7alpha- and 12alpha-hydroxysteroid dehydrogenases