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3,12-diketocholanoic acid + NADP+
?
-
-
-
-
r
3,7,12-triketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-3,12-diketo-5beta-cholanoic acid + NADP+
-
-
-
?
3,7,12-triketo-5beta-cholanoyl taurine + NADPH
7beta-hydroxy-3,12-diketo-5beta-cholanoyl taurine + NADP+
-
-
-
?
3,7-diketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-3-keto-5beta-cholanoic acid + NADP+
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
3alpha,7beta-dihydroxy-5beta-cholan-24-oic acid + NADP+
7-oxo-lithocholic acid + NADPH + H+
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
3alpha,7beta-dihydroxy-5beta-cholanoyl glycine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl glycine + NADPH
3alpha,7beta-dihydroxy-5beta-cholanoyl taurine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl taurine + NADPH
3alpha-hydroxy-7,12-diketo-5beta-cholanoic acid + NADPH
3alpha,7beta-dihydroxy-12-keto-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholan-24-oic acid + NADPH + H+
3alpha,7beta-dihydroxy-5beta-cholan-24-oic acid + NADP+
5-cholesten-3beta,7beta-diol + NADP+
5-cholesten-3beta-ol-7-one + NADPH
-
i.e. 7beta-hydroxycholesterol
-
-
?
7,12-diketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-12-keto-5beta-cholanoic acid + NADP+
7,12-dioxo-ursodeoxycholic acid + NADPH + H+
12-oxo-ursodeoxycholic acid + NADP+
7-ketolithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
7-oxo-lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
7beta-hydroxycholesterol + NADP+
7-oxocholesterol + NADPH
-
-
-
-
?
7beta-hydroxysteroid + NADP+
7-oxosteroid + NADPH + H+
chenodeoxycholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
corticosterone + NADP+
21-hydroxy-pregn-4-ene-3,11,20-trione + NADPH
-
oxidation at C-11
-
-
?
cortisone + NADP+
? + NADPH
-
oxidation at C-11
-
-
?
dehydrocholic acid + NADPH + H+
12-oxo-ursodeoxycholic acid + NADP+
dehydrocholic acid + NADPH + H+
? + NADP+ + H+
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
ursodeoxycholic acid + NADP+
7-ketolithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
7-oxo-lithocholic acid + NADPH + H+
additional information
?
-
3,7-diketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-3-keto-5beta-cholanoic acid + NADP+
-
-
-
?
3,7-diketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-3-keto-5beta-cholanoic acid + NADP+
-
-
-
?
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
-
-
-
?
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
-
-
-
?
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
-
partially reversible, poor substrate
-
r
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
-
ursocholic acid
-
r
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
-
ursocholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholan-24-oic acid + NADP+
7-oxo-lithocholic acid + NADPH + H+
i.e. ursodeoxycholic acid, exclusive specificity for the hydroxyl group in beta configuration at the C-7 position
-
-
r
3alpha,7beta-dihydroxy-5beta-cholan-24-oic acid + NADP+
7-oxo-lithocholic acid + NADPH + H+
i.e. ursodeoxycholic acid, exclusive specificity for the hydroxyl group in beta configuration at the C-7 position
-
-
r
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
only active on free and conjugated bile salts
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
activity only in the reductive reaction
-
-
ir
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
activity only in the reductive reaction
-
-
ir
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
r
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
partially reversible
-
r
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
only active on free and conjugated bile salts
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
active on both free and conjugated bile salts
-
?
3alpha,7beta-dihydroxy-5beta-cholanoyl glycine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl glycine + NADPH
-
-
-
?
3alpha,7beta-dihydroxy-5beta-cholanoyl glycine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl glycine + NADPH
-
-
-
?
3alpha,7beta-dihydroxy-5beta-cholanoyl taurine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl taurine + NADPH
-
-
-
?
3alpha,7beta-dihydroxy-5beta-cholanoyl taurine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl taurine + NADPH
-
-
-
?
3alpha,7beta-dihydroxy-5beta-cholanoyl taurine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl taurine + NADPH
-
partially reversible, poore substrate
-
r
3alpha-hydroxy-7,12-diketo-5beta-cholanoic acid + NADPH
3alpha,7beta-dihydroxy-12-keto-5beta-cholanoic acid + NADP+
-
-
-
?
3alpha-hydroxy-7,12-diketo-5beta-cholanoic acid + NADPH
3alpha,7beta-dihydroxy-12-keto-5beta-cholanoic acid + NADP+
-
-
-
?
3alpha-hydroxy-7-oxo-5beta-cholan-24-oic acid + NADPH + H+
3alpha,7beta-dihydroxy-5beta-cholan-24-oic acid + NADP+
i.e. 7-oxo-lithocholic acid
i.e. ursodeoxycholic acid
-
r
3alpha-hydroxy-7-oxo-5beta-cholan-24-oic acid + NADPH + H+
3alpha,7beta-dihydroxy-5beta-cholan-24-oic acid + NADP+
i.e 7-oxo-lithocholic acid, the forward reaction is preferred, formation of ursodeoxycholic acid
i.e. ursodeoxycholic acid
-
r
3alpha-hydroxy-7-oxo-5beta-cholan-24-oic acid + NADPH + H+
3alpha,7beta-dihydroxy-5beta-cholan-24-oic acid + NADP+
i.e. 7-oxo-lithocholic acid
i.e. ursodeoxycholic acid
-
r
3alpha-hydroxy-7-oxo-5beta-cholan-24-oic acid + NADPH + H+
3alpha,7beta-dihydroxy-5beta-cholan-24-oic acid + NADP+
i.e 7-oxo-lithocholic acid, the forward reaction is preferred, formation of ursodeoxycholic acid
i.e. ursodeoxycholic acid
-
r
7,12-diketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-12-keto-5beta-cholanoic acid + NADP+
-
-
-
?
7,12-diketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-12-keto-5beta-cholanoic acid + NADP+
-
-
-
?
7,12-dioxo-ursodeoxycholic acid + NADPH + H+
12-oxo-ursodeoxycholic acid + NADP+
-
-
-
-
?
7,12-dioxo-ursodeoxycholic acid + NADPH + H+
12-oxo-ursodeoxycholic acid + NADP+
-
-
-
-
?
7,12-dioxo-ursodeoxycholic acid + NADPH + H+
12-oxo-ursodeoxycholic acid + NADP+
-
-
-
-
?
7,12-dioxo-ursodeoxycholic acid + NADPH + H+
12-oxo-ursodeoxycholic acid + NADP+
-
-
-
-
?
7,12-dioxo-ursodeoxycholic acid + NADPH + H+
12-oxo-ursodeoxycholic acid + NADP+
-
-
-
-
?
7-ketolithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
only product, 90% conversion, 71% yield
-
r
7-ketolithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
only product, 90% conversion, 71% yield
-
r
7-oxo-lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
7-oxo-lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
after a first reaction step with EC 1.1.1.159, 7alpha-hydroxysteroid dehydrogenase, from chenodeoxycholic acid
-
-
?
7-oxo-lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
after a first reaction step with EC 1.1.1.159, 7alpha-hydroxysteroid dehydrogenase, from chenodeoxycholic acid
-
-
?
7-oxo-lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
7beta-hydroxysteroid + NADP+
7-oxosteroid + NADPH + H+
-
-
-
r
7beta-hydroxysteroid + NADP+
7-oxosteroid + NADPH + H+
stereoselective with 7-beta-hydroxysteroids
-
-
r
7beta-hydroxysteroid + NADP+
7-oxosteroid + NADPH + H+
-
-
-
r
7beta-hydroxysteroid + NADP+
7-oxosteroid + NADPH + H+
stereoselective with 7-beta-hydroxysteroids
-
-
r
chenodeoxycholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
chenodeoxycholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
chenodeoxycholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
chenodeoxycholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
chenodeoxycholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
dehydrocholic acid + NADPH + H+
12-oxo-ursodeoxycholic acid + NADP+
-
-
-
-
?
dehydrocholic acid + NADPH + H+
12-oxo-ursodeoxycholic acid + NADP+
-
-
-
-
?
dehydrocholic acid + NADPH + H+
12-oxo-ursodeoxycholic acid + NADP+
-
-
-
-
?
dehydrocholic acid + NADPH + H+
12-oxo-ursodeoxycholic acid + NADP+
-
-
-
-
?
dehydrocholic acid + NADPH + H+
12-oxo-ursodeoxycholic acid + NADP+
-
-
-
-
?
dehydrocholic acid + NADPH + H+
? + NADP+ + H+
-
-
-
-
?
dehydrocholic acid + NADPH + H+
? + NADP+ + H+
-
-
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
presence of both 7alpha-HSDH (EC 1.1.1.159) and 7beta-HSDH in one organism allows epimerization by a single bacterium
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
presence of both 7alpha-HSDH (EC 1.1.1.159) and 7beta-HSDH in one organism allows epimerization by a single bacterium
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
presence of both 7alpha-HSDH (EC 1.1.1.159) and 7beta-HSDH in one organism allows epimerization by a single bacterium
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
presence of both 7alpha-HSDH (EC 1.1.1.159) and 7beta-HSDH in one organism allows epimerization by a single bacterium
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
presence of both 7alpha-HSDH (EC 1.1.1.159) and 7beta-HSDH in one organism allows epimerization by a single bacterium
-
-
?
ursodeoxycholic acid + NADP+
7-ketolithocholic acid + NADPH + H+
-
-
-
-
r
ursodeoxycholic acid + NADP+
7-ketolithocholic acid + NADPH + H+
-
-
-
-
r
ursodeoxycholic acid + NADP+
7-oxo-lithocholic acid + NADPH + H+
-
-
-
r
ursodeoxycholic acid + NADP+
7-oxo-lithocholic acid + NADPH + H+
-
-
-
r
additional information
?
-
no activity with chenodeoxycholic acid, i.e. 3alpha,7alpha-dihydroxy-5beta-cholan-24-oic acid
-
-
?
additional information
?
-
no activity with chenodeoxycholic acid, i.e. 3alpha,7alpha-dihydroxy-5beta-cholan-24-oic acid
-
-
?
additional information
?
-
-
enzyme might also show 11beta-hydroxysteroid dehydrogenase activity, no activity with cholesterol, 7alpha-hydroxycholesterol, 25-hydroxycholesterol, pregnenolone, dehydroepiandrosterone, chenodoxycolic acid, and ursodeoxycholic acid
-
-
?
additional information
?
-
in vivo, the forward reaction that produces ursodeoxycholic acid from 7-oxo-lithocholic acid is observed to have a growth-dependent conversion rate of 90-100% after culture in anaerobic medium broth containing 1 mM 7-oxo-lithocholic acid, while the reverse reaction is undetectable. The purified 7beta-HSDH shows a kcat/Km value that is about 55fold higher for the forward reaction than for the reverse reaction, indicating that the enzyme favors the UDCA producing reaction
-
-
?
additional information
?
-
in vivo, the forward reaction that produces ursodeoxycholic acid from 7-oxo-lithocholic acid is observed to have a growth-dependent conversion rate of 90-100% after culture in anaerobic medium broth containing 1 mM 7-oxo-lithocholic acid, while the reverse reaction is undetectable. The purified 7beta-HSDH shows a kcat/Km value that is about 55fold higher for the forward reaction than for the reverse reaction, indicating that the enzyme favors the UDCA producing reaction
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
3,7,12-triketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-3,12-diketo-5beta-cholanoic acid + NADP+
-
-
-
?
3,7,12-triketo-5beta-cholanoyl taurine + NADPH
7beta-hydroxy-3,12-diketo-5beta-cholanoyl taurine + NADP+
-
-
-
?
3,7-diketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-3-keto-5beta-cholanoic acid + NADP+
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
3alpha,7beta-dihydroxy-5beta-cholanoyl glycine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl glycine + NADPH
3alpha,7beta-dihydroxy-5beta-cholanoyl taurine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl taurine + NADPH
3alpha-hydroxy-7,12-diketo-5beta-cholanoic acid + NADPH
3alpha,7beta-dihydroxy-12-keto-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholan-24-oic acid + NADPH + H+
3alpha,7beta-dihydroxy-5beta-cholan-24-oic acid + NADP+
7,12-diketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-12-keto-5beta-cholanoic acid + NADP+
7beta-hydroxycholesterol + NADP+
7-oxocholesterol + NADPH
-
-
-
-
?
7beta-hydroxysteroid + NADP+
7-oxosteroid + NADPH + H+
chenodeoxycholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
ursodeoxycholic acid + NADP+
7-oxo-lithocholic acid + NADPH + H+
additional information
?
-
3,7-diketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-3-keto-5beta-cholanoic acid + NADP+
-
-
-
?
3,7-diketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-3-keto-5beta-cholanoic acid + NADP+
-
-
-
?
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
-
-
-
?
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
-
-
-
?
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
-
partially reversible, poor substrate
-
r
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
-
ursocholic acid
-
r
3alpha,7beta,12alpha-trihydroxy-5beta-cholanoic acid + NADP+
3alpha,12alpha-dihydroxy-7-keto-5beta-cholanoic acid + NADPH
-
ursocholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
only active on free and conjugated bile salts
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
activity only in the reductive reaction
-
-
ir
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
activity only in the reductive reaction
-
-
ir
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
r
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
partially reversible
-
r
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
only active on free and conjugated bile salts
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
ursodeoxycholic acid
-
?
3alpha,7beta-dihydroxy-5beta-cholanoic acid + NADP+
3alpha-hydroxy-7-oxo-5beta-cholanoic acid + NADPH
-
active on both free and conjugated bile salts
-
?
3alpha,7beta-dihydroxy-5beta-cholanoyl glycine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl glycine + NADPH
-
-
-
?
3alpha,7beta-dihydroxy-5beta-cholanoyl glycine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl glycine + NADPH
-
-
-
?
3alpha,7beta-dihydroxy-5beta-cholanoyl taurine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl taurine + NADPH
-
-
-
?
3alpha,7beta-dihydroxy-5beta-cholanoyl taurine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl taurine + NADPH
-
-
-
?
3alpha,7beta-dihydroxy-5beta-cholanoyl taurine + NADP+
3alpha-hydroxy-7-keto-5beta-cholanoyl taurine + NADPH
-
partially reversible, poore substrate
-
r
3alpha-hydroxy-7,12-diketo-5beta-cholanoic acid + NADPH
3alpha,7beta-dihydroxy-12-keto-5beta-cholanoic acid + NADP+
-
-
-
?
3alpha-hydroxy-7,12-diketo-5beta-cholanoic acid + NADPH
3alpha,7beta-dihydroxy-12-keto-5beta-cholanoic acid + NADP+
-
-
-
?
3alpha-hydroxy-7-oxo-5beta-cholan-24-oic acid + NADPH + H+
3alpha,7beta-dihydroxy-5beta-cholan-24-oic acid + NADP+
i.e. 7-oxo-lithocholic acid
i.e. ursodeoxycholic acid
-
r
3alpha-hydroxy-7-oxo-5beta-cholan-24-oic acid + NADPH + H+
3alpha,7beta-dihydroxy-5beta-cholan-24-oic acid + NADP+
i.e. 7-oxo-lithocholic acid
i.e. ursodeoxycholic acid
-
r
7,12-diketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-12-keto-5beta-cholanoic acid + NADP+
-
-
-
?
7,12-diketo-5beta-cholanoic acid + NADPH
7beta-hydroxy-12-keto-5beta-cholanoic acid + NADP+
-
-
-
?
7beta-hydroxysteroid + NADP+
7-oxosteroid + NADPH + H+
-
-
-
r
7beta-hydroxysteroid + NADP+
7-oxosteroid + NADPH + H+
-
-
-
r
chenodeoxycholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
chenodeoxycholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
chenodeoxycholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
chenodeoxycholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
chenodeoxycholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
presence of both 7alpha-HSDH (EC 1.1.1.159) and 7beta-HSDH in one organism allows epimerization by a single bacterium
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
lithocholic acid + NADPH + H+
ursodeoxycholic acid + NADP+
-
-
-
-
?
ursodeoxycholic acid + NADP+
7-oxo-lithocholic acid + NADPH + H+
-
-
-
r
ursodeoxycholic acid + NADP+
7-oxo-lithocholic acid + NADPH + H+
-
-
-
r
additional information
?
-
in vivo, the forward reaction that produces ursodeoxycholic acid from 7-oxo-lithocholic acid is observed to have a growth-dependent conversion rate of 90-100% after culture in anaerobic medium broth containing 1 mM 7-oxo-lithocholic acid, while the reverse reaction is undetectable. The purified 7beta-HSDH shows a kcat/Km value that is about 55fold higher for the forward reaction than for the reverse reaction, indicating that the enzyme favors the UDCA producing reaction
-
-
?
additional information
?
-
in vivo, the forward reaction that produces ursodeoxycholic acid from 7-oxo-lithocholic acid is observed to have a growth-dependent conversion rate of 90-100% after culture in anaerobic medium broth containing 1 mM 7-oxo-lithocholic acid, while the reverse reaction is undetectable. The purified 7beta-HSDH shows a kcat/Km value that is about 55fold higher for the forward reaction than for the reverse reaction, indicating that the enzyme favors the UDCA producing reaction
-
-
?
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Bile induction of 7alpha- and 7beta-hydroxysteroid dehydrogenases in Clostridium absonum
Biochim. Biophys. Acta
665
262-269
1981
Clostridium sardiniense
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Formation of ursodeoxycholic acid from chenodeoxycholic acid by a 7beta-hydroxysteroid dehydrogenase-elaborating Eubacterium aerofaciens strain cocultured with 7alpha-hydroxysteroid dehydrogenase-elaborating organisms
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44
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brenda
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Clostridium sp., Clostridium sp. 25.11.c
brenda
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91
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Oryctolagus cuniculus
brenda
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90
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2011
Collinsella aerofaciens, Collinsella aerofaciens DSM 3979
brenda
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Enzymatic routes for the synthesis of ursodeoxycholic acid
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191
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2014
Clostridium sardiniense, [Clostridium] scindens, Paeniclostridium sordellii, Collinsella aerofaciens, Fusarium equiseti
brenda
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Contribution of the 7beta-hydroxysteroid dehydrogenase from Ruminococcus gnavus N53 to ursodeoxycholic acid formation in the human colon
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54
3062-3069
2013
[Ruminococcus] gnavus (A7B4V1), [Ruminococcus] gnavus ATCC 29149 (A7B4V1)
brenda
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Structural and biochemical insights into 7beta-hydroxysteroid dehydrogenase stereoselectivity
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Collinsella aerofaciens (A4ECA9), Collinsella aerofaciens ATCC 25986 (A4ECA9)
brenda
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Structure of NADP+-bound 7beta-hydroxysteroid dehydrogenase reveals two cofactor-binding modes
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73
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2017
Collinsella aerofaciens, Collinsella aerofaciens ATCC 25986
brenda
Zhang, X.; Fan, D.; Hua, X.; Zhang, T.
Large-scale production of ursodeoxycholic acid from chenodeoxycholic acid by engineering 7alpha- and 7beta-hydroxysteroid dehydrogenase
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42
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[Ruminococcus] torques, [Ruminococcus] torques ATCC 35915
brenda
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65
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[Ruminococcus] torques, [Ruminococcus] torques ATCC 35915
brenda