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Literature summary for 1.1.1.149 extracted from

  • Hara, A.; Inazu, A.; Deyashiki, Y.; Nozawa, Y.
    Substrate specificity and kinetic mechanism of Tetrahymena 20alpha-hydroxysteroid dehydrogenase (1995), Adv. Exp. Med. Biol., 372, 249-258.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
Bile acids e.g. lithocholic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena pyriformis
Bile acids e.g. lithocholic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena thermophila
cibacron coenzyme analog, competitively with respect to both coenzymes Tetrahymena pyriformis
cibacron coenzyme analog, competitively with respect to both coenzymes Tetrahymena thermophila
Dienstrol competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena pyriformis
Dienstrol competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena thermophila
ethyl acetate noncompetitively with respect to NADP+ and (S)-ethyl 3-hydroxybutyrate at backward reaction Tetrahymena pyriformis
ethyl acetate noncompetitively with respect to NADP+ and (S)-ethyl 3-hydroxybutyrate at backward reaction Tetrahymena thermophila
fatty acids e.g. myristic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena pyriformis
fatty acids e.g. myristic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena thermophila
NADP+ (non)competitively with respect to NADPH and ethyl acetoacetate at forward reaction Tetrahymena pyriformis
NADP+ (non)competitively with respect to NADPH and ethyl acetoacetate at forward reaction Tetrahymena thermophila
Phenobarbital competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena pyriformis
Phenobarbital competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena thermophila
quercitrin competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena pyriformis
quercitrin competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena thermophila
sorbinil competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena pyriformis
sorbinil competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena thermophila
Tolrestat competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena pyriformis
Tolrestat competitive with respect to (S)-ethyl 3-hydroxybutyrate Tetrahymena thermophila

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0013
-
n-octyl acetoacetate
-
Tetrahymena pyriformis
0.0015
-
n-hexyl acetoacetate
-
Tetrahymena pyriformis
0.0016
-
n-octyl acetoacetate
-
Tetrahymena thermophila
0.002
-
NADPH +/-0.0001, ethyl acetoacetate Tetrahymena thermophila
0.002 0.003 17alpha-hydroxypregnenolone
-
Tetrahymena pyriformis
0.002 0.003 17alpha-hydroxypregnenolone
-
Tetrahymena thermophila
0.0024
-
n-hexyl acetoacetate
-
Tetrahymena thermophila
0.003
-
17alpha-hydroxyprogesterone
-
Tetrahymena pyriformis
0.003
-
17alpha-hydroxyprogesterone
-
Tetrahymena thermophila
0.004
-
n-butyl acetoacetate
-
Tetrahymena pyriformis
0.004
-
n-butyl acetoacetate
-
Tetrahymena thermophila
0.005 0.008 2,3-heptanedione
-
Tetrahymena pyriformis
0.005 0.008 2,3-heptanedione
-
Tetrahymena thermophila
0.006
-
1-phenyl-1,2-propanedione
-
Tetrahymena pyriformis
0.006
-
1-phenyl-1,2-propanedione
-
Tetrahymena thermophila
0.008
-
benzyl acetoacetate
-
Tetrahymena pyriformis
0.008
-
benzyl acetoacetate
-
Tetrahymena thermophila
0.01 0.016 2,3-Hexanedione
-
Tetrahymena pyriformis
0.01 0.016 2,3-Hexanedione
-
Tetrahymena thermophila
0.012
-
NADP+ +/-0.001, (S)-ethyl 3-hydroxybutyrate Tetrahymena thermophila
0.012 0.015 ethyl 2-methylacetoacetate
-
Tetrahymena pyriformis
0.012 0.015 ethyl 2-methylacetoacetate
-
Tetrahymena thermophila
0.013 0.014 17alpha,20alpha-dihydroxyprogesterone
-
Tetrahymena pyriformis
0.013 0.014 17alpha,20alpha-dihydroxyprogesterone
-
Tetrahymena thermophila
0.015 0.018 2,3-Butanedione
-
Tetrahymena pyriformis
0.015 0.018 2,3-Butanedione
-
Tetrahymena thermophila
0.018 0.021 2,3-Pentanedione
-
Tetrahymena pyriformis
0.018 0.021 2,3-Pentanedione
-
Tetrahymena thermophila
0.02 0.032 ethyl acetoacetate
-
Tetrahymena pyriformis
0.02 0.032 ethyl acetoacetate
-
Tetrahymena thermophila
0.02 0.022 acetoacetyl-CoA
-
Tetrahymena pyriformis
0.02 0.022 acetoacetyl-CoA
-
Tetrahymena thermophila
0.025
-
ethyl pyruvate
-
Tetrahymena pyriformis
0.025
-
ethyl pyruvate
-
Tetrahymena thermophila
0.027
-
ethyl 4-chloroacetoacetate
-
Tetrahymena pyriformis
0.027
-
ethyl 4-chloroacetoacetate
-
Tetrahymena thermophila
0.039 0.045 isatin
-
Tetrahymena pyriformis
0.039 0.045 isatin
-
Tetrahymena thermophila
0.049 0.051 Pyridine-3-aldehyde
-
Tetrahymena pyriformis
0.049 0.051 Pyridine-3-aldehyde
-
Tetrahymena thermophila
0.073
-
5beta-pregnan-20alpha-ol-3-one
-
Tetrahymena pyriformis
0.092 0.129 1,2-Cyclohexanedione
-
Tetrahymena thermophila
0.117 0.123 methyl acetoacetate
-
Tetrahymena thermophila
0.123
-
methyl acetoacetate
-
Tetrahymena pyriformis
0.129
-
1,2-Cyclohexanedione
-
Tetrahymena pyriformis
0.131 0.243 2,4-Pentanedione
-
Tetrahymena thermophila
0.186 0.272 acetoin
-
Tetrahymena pyriformis
0.221 0.254 4-nitrobenzaldehyde
-
Tetrahymena pyriformis
0.221 0.254 4-nitrobenzaldehyde
-
Tetrahymena thermophila
0.222 0.447 ethyl 3-oxovalerate
-
Tetrahymena thermophila
0.23 0.57 3,4-hexanedione
-
Tetrahymena thermophila
0.243
-
2,4-Pentanedione
-
Tetrahymena pyriformis
0.272
-
acetoin
-
Tetrahymena thermophila
0.3 0.464 D-glyceraldehyde
-
Tetrahymena pyriformis
0.303 0.654 ethyl benzoylacetate
-
Tetrahymena thermophila
0.356 0.548 methylglyoxal
-
Tetrahymena pyriformis
0.356 0.548 methylglyoxal
-
Tetrahymena thermophila
0.447
-
ethyl 3-oxovalerate
-
Tetrahymena pyriformis
0.447 0.591 Phenylglyoxal
-
Tetrahymena thermophila
0.464
-
D-glyceraldehyde
-
Tetrahymena thermophila
0.534 0.587 D-Lactaldehyde
-
Tetrahymena thermophila
0.57
-
3,4-hexanedione
-
Tetrahymena pyriformis
0.587
-
D-Lactaldehyde
-
Tetrahymena pyriformis
0.591
-
Phenylglyoxal
-
Tetrahymena pyriformis
0.654
-
ethyl benzoylacetate
-
Tetrahymena pyriformis
0.852 1.3 DL-glyceraldehyde 3-phosphate
-
Tetrahymena thermophila
0.945 1.06 Pyridine-4-aldehyde
-
Tetrahymena thermophila
1 1.3 (S)-ethyl 3-hydroxybutyrate
-
Tetrahymena pyriformis
1 1.3 (S)-ethyl 3-hydroxybutyrate
-
Tetrahymena thermophila
1.06
-
Pyridine-4-aldehyde
-
Tetrahymena pyriformis
1.3
-
DL-glyceraldehyde 3-phosphate
-
Tetrahymena pyriformis
1.6
-
trans-benzene-1S,2S-dihydrodiol
-
Tetrahymena pyriformis
1.6
-
trans-benzene-1S,2S-dihydrodiol
-
Tetrahymena thermophila
2.02 2.9 cis-benzene-1,2-dihydrodiol racemic Tetrahymena pyriformis
2.9
-
cis-benzene-1,2-dihydrodiol racemic Tetrahymena thermophila
4.8 5 (S)-methyl 3-hydroxybutyrate
-
Tetrahymena pyriformis
4.8 5 (S)-methyl 3-hydroxybutyrate
-
Tetrahymena thermophila
20
-
ethyl acetoacetate +/-1 Tetrahymena thermophila
34.8 66.3 2,3-Butanediol
-
Tetrahymena pyriformis
50.9 79.7 trans-1S,2S-cyclohexanediol
-
Tetrahymena pyriformis
66.3
-
2,3-Butanediol
-
Tetrahymena thermophila
79.7
-
trans-1S,2S-cyclohexanediol
-
Tetrahymena thermophila
1870
-
(S)-ethyl 3-hydroxybutyrate +/-60 Tetrahymena thermophila

Molecular Weight [Da]

Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
33000
-
2 * 33000, SDS-PAGE Tetrahymena pyriformis
33000
-
2 * 33000, SDS-PAGE Tetrahymena thermophila
68000
-
-
Tetrahymena pyriformis
68000
-
-
Tetrahymena thermophila

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Tetrahymena pyriformis role of enzyme suggested to be for detoxication or metabolism of carbonyl compounds because of broad substrate specificity ?
-
?
additional information Tetrahymena thermophila role of enzyme suggested to be for detoxication or metabolism of carbonyl compounds because of broad substrate specificity ?
-
?

Organism

Organism UniProt Comment Textmining
Tetrahymena pyriformis
-
-
-
Tetrahymena thermophila
-
-
-

Purification (Commentary)

Purification (Comment) Organism
co-purification with aldehyde reductase and dihydrodiol dehydrogenase Tetrahymena pyriformis
five steps co-purification with aldehyde reductase and dihydrodiol dehydrogenase, ammonium sulfate precipitation, HPLC Tetrahymena thermophila

Reaction

Reaction Comment Organism Reaction ID
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+ = 17alpha-hydroxyprogesterone + NAD(P)H + H+ aldoketo reductase superfamily Tetrahymena pyriformis
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+ = 17alpha-hydroxyprogesterone + NAD(P)H + H+ aldoketo reductase superfamily Tetrahymena thermophila
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+ = 17alpha-hydroxyprogesterone + NAD(P)H + H+ bibi mechanism Tetrahymena pyriformis
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+ = 17alpha-hydroxyprogesterone + NAD(P)H + H+ bibi mechanism Tetrahymena thermophila

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
0.012
-
+/-0.005 Tetrahymena pyriformis
0.024
-
+/-0.006 Tetrahymena thermophila
5
-
-
Tetrahymena thermophila

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(S)-methyl 3-hydroxybutyrate + NADP+
-
Tetrahymena pyriformis methyl acetoacetate + NADPH + H+
-
r
(S)-methyl 3-hydroxybutyrate + NADP+
-
Tetrahymena thermophila methyl acetoacetate + NADPH + H+
-
r
1,2-cyclohexanedione + NADP+ 66% activity compared to pyridine 3-aldehyde Tetrahymena pyriformis ?
-
r
1,2-cyclohexanedione + NADP+ 50% activity compared to pyridine 3-aldehyde Tetrahymena thermophila ?
-
r
1-phenyl-1,2-propanedione + NADPH
-
Tetrahymena pyriformis NADP+ + ?
-
?
1-phenyl-1,2-propanedione + NADPH
-
Tetrahymena thermophila NADP+ + ?
-
?
17alpha-hydroxypregnenolone + NADPH
-
Tetrahymena pyriformis ? + NADP+
-
?
17alpha-hydroxypregnenolone + NADPH
-
Tetrahymena thermophila ? + NADP+
-
?
17alpha-hydroxyprogesterone + NADPH + H+
-
Tetrahymena pyriformis 17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
r
17alpha-hydroxyprogesterone + NADPH + H+
-
Tetrahymena thermophila 17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
r
2,3-butanediol + NADP+
-
Tetrahymena pyriformis ?
-
r
2,3-butanediol + NADP+
-
Tetrahymena thermophila ?
-
r
2,3-butanedione + NADPH
-
Tetrahymena pyriformis ? + NADP+
-
?
2,3-butanedione + NADPH
-
Tetrahymena thermophila ? + NADP+
-
?
2,3-heptanedione + NADPH
-
Tetrahymena pyriformis NADP+ + ?
-
?
2,3-heptanedione + NADPH
-
Tetrahymena thermophila NADP+ + ?
-
?
2,3-hexanedione + NADPH
-
Tetrahymena pyriformis NADP+ + ?
-
?
2,3-hexanedione + NADPH
-
Tetrahymena thermophila NADP+ + ?
-
?
2,3-pentanedione + NADPH
-
Tetrahymena pyriformis NADP+ + ?
-
?
2,3-pentanedione + NADPH
-
Tetrahymena thermophila NADP+ + ?
-
?
2,4-pentanedione + NADP+
-
Tetrahymena pyriformis ?
-
r
2,4-pentanedione + NADP+
-
Tetrahymena thermophila ?
-
r
3,4-hexanedione + NADP+
-
Tetrahymena pyriformis ?
-
r
3,4-hexanedione + NADP+
-
Tetrahymena thermophila ?
-
r
4-nitrobenzaldehyde + NADPH
-
Tetrahymena pyriformis 4-nitrobenzyl alcohol + NADP+
-
?
4-nitrobenzaldehyde + NADPH
-
Tetrahymena thermophila 4-nitrobenzyl alcohol + NADP+
-
?
5beta-pregnan-20alpha-ol-3-one + NADP+
-
Tetrahymena pyriformis ?
-
r
acetoacetyl-CoA + NADPH
-
Tetrahymena pyriformis NADP+ + ?
-
?
acetoacetyl-CoA + NADPH
-
Tetrahymena thermophila NADP+ + ?
-
?
acetoin + NADPH + H+
-
Tetrahymena pyriformis ?
-
r
acetoin + NADPH + H+
-
Tetrahymena thermophila ?
-
r
benzyl acetoacetate + NADPH + H+
-
Tetrahymena pyriformis ?
-
r
benzyl acetoacetate + NADPH + H+
-
Tetrahymena thermophila ?
-
r
cis-benzene-1,2-dihydrodiol + NADP+
-
Tetrahymena pyriformis ?
-
r
cis-benzene-1,2-dihydrodiol + NADP+
-
Tetrahymena thermophila ?
-
r
D-glyceraldehyde + NADPH + H+
-
Tetrahymena pyriformis glycerol + NADP+
-
r
D-glyceraldehyde + NADPH + H+
-
Tetrahymena thermophila glycerol + NADP+
-
r
D-lactaldehyde + NADPH + H+
-
Tetrahymena pyriformis ?
-
r
D-lactaldehyde + NADPH + H+
-
Tetrahymena thermophila ?
-
r
DL-glyceraldehyde 3-phosphate + NADPH + H+
-
Tetrahymena pyriformis glycerol 3-phosphate + NADP+
-
r
DL-glyceraldehyde 3-phosphate + NADPH + H+
-
Tetrahymena thermophila glycerol 3-phosphate + NADP+
-
r
ethyl 2-methylacetoacetate + NADPH
-
Tetrahymena pyriformis NADP+ + ?
-
?
ethyl 2-methylacetoacetate + NADPH
-
Tetrahymena thermophila NADP+ + ?
-
?
ethyl 3-oxovalerate + NADPH + H+
-
Tetrahymena pyriformis ?
-
r
ethyl 3-oxovalerate + NADPH + H+
-
Tetrahymena thermophila ?
-
r
ethyl 4-chloroacetoacetate + NADPH
-
Tetrahymena pyriformis NADP+ + ?
-
?
ethyl 4-chloroacetoacetate + NADPH
-
Tetrahymena thermophila NADP+ + ?
-
?
ethyl acetoaetate + NADPH
-
Tetrahymena thermophila (S)-ethyl 3-hydroxybutyrate + NADP+
-
r
ethyl benzoylacetate + NADPH + H+
-
Tetrahymena pyriformis ?
-
r
ethyl benzoylacetate + NADPH + H+
-
Tetrahymena thermophila ?
-
r
ethyl pyruvate + NADPH
-
Tetrahymena pyriformis NADP+ + ?
-
?
ethyl pyruvate + NADPH
-
Tetrahymena thermophila NADP+ + ?
-
?
isatin + NADPH
-
Tetrahymena pyriformis NADP+ + ?
-
?
isatin + NADPH
-
Tetrahymena thermophila NADP+ + ?
-
?
methyl acetoacetate + NADPH + H+
-
Tetrahymena pyriformis ?
-
r
methyl acetoacetate + NADPH + H+
-
Tetrahymena thermophila ?
-
r
methylglyoxal + NADPH
-
Tetrahymena pyriformis NADP+ + ?
-
?
methylglyoxal + NADPH
-
Tetrahymena thermophila NADP+ + ?
-
?
additional information other substrates: 2,3-butanedione to 2,3-heptanedione, 1-phenyl-1,2-propanedione, ethyl 2-methylacetoacetate, acetoacetyl-CoA, ethyl pyruvate, ethyl 4-chloroacetoacetate, isatin, pyridine-3-aldehyde , not 20beta-hydroxysteroids, 1,2-cyclohexanedione, methyl acetoacetate, 2,4-pentanedione, acetoin, 4-nitrobenzaldehyde, ethyl 3-oxovalerate, 3,4-hexanedione, D-glyceraldehyde, ethyl benzoylacetate, D-lactaldehyde, DL-glceraldehyde 3-phosphate, pyridine-4-aldehyde, (S)-ethyl-3-hydroxybutyrate, trans-benzene-1S,2S-dihydrodiol, cis-benzene-1,2-dihydrodiol, (S)-methyl 3-hydroxybutyrate Tetrahymena pyriformis ?
-
?
additional information other substrates: 2,3-butanedione to 2,3-heptanedione, 1-phenyl-1,2-propanedione, ethyl 2-methylacetoacetate, acetoacetyl-CoA, ethyl pyruvate, ethyl 4-chloroacetoacetate, isatin, pyridine-3-aldehyde , not 20beta-hydroxysteroids, 1,2-cyclohexanedione, methyl acetoacetate, 2,4-pentanedione, acetoin, 4-nitrobenzaldehyde, ethyl 3-oxovalerate, 3,4-hexanedione, D-glyceraldehyde, ethyl benzoylacetate, D-lactaldehyde, DL-glceraldehyde 3-phosphate, pyridine-4-aldehyde, (S)-ethyl-3-hydroxybutyrate, trans-benzene-1S,2S-dihydrodiol, cis-benzene-1,2-dihydrodiol, (S)-methyl 3-hydroxybutyrate Tetrahymena thermophila ?
-
?
additional information role of enzyme suggested to be for detoxication or metabolism of carbonyl compounds because of broad substrate specificity Tetrahymena pyriformis ?
-
?
additional information role of enzyme suggested to be for detoxication or metabolism of carbonyl compounds because of broad substrate specificity Tetrahymena thermophila ?
-
?
n-butyl acetoacetate + NADPH + H+
-
Tetrahymena pyriformis ?
-
r
n-butyl acetoacetate + NADPH + H+
-
Tetrahymena thermophila ?
-
r
n-hexyl acetoacetate + NADPH + H+
-
Tetrahymena pyriformis ?
-
r
n-hexyl acetoacetate + NADPH + H+
-
Tetrahymena thermophila ?
-
r
n-octyl acetoacetate + NADPH + H+
-
Tetrahymena pyriformis ?
-
r
n-octyl acetoacetate + NADPH + H+
-
Tetrahymena thermophila ?
-
r
phenylglyoxal + NADP+
-
Tetrahymena pyriformis ?
-
r
phenylglyoxal + NADP+
-
Tetrahymena thermophila ?
-
r
pyridine-3-aldehyde + NADPH
-
Tetrahymena pyriformis NADP+ + ?
-
?
pyridine-3-aldehyde + NADPH
-
Tetrahymena thermophila NADP+ + ?
-
?
pyridine-4-aldehyde + NADP+
-
Tetrahymena pyriformis ?
-
r
pyridine-4-aldehyde + NADP+
-
Tetrahymena thermophila ?
-
r
trans-1S,2S-cyclohexanediol + NADP+
-
Tetrahymena pyriformis ?
-
r
trans-1S,2S-cyclohexanediol + NADP+
-
Tetrahymena thermophila ?
-
r
trans-benzene-1S,2S-dihydrodiol + NADP+
-
Tetrahymena pyriformis ?
-
r
trans-benzene-1S,2S-dihydrodiol + NADP+
-
Tetrahymena thermophila ?
-
r

Subunits

Subunits Comment Organism
dimer 2 * 33000, SDS-PAGE Tetrahymena pyriformis
dimer 2 * 33000, SDS-PAGE Tetrahymena thermophila

Cofactor

Cofactor Comment Organism Structure
NADP+
-
Tetrahymena pyriformis
NADP+
-
Tetrahymena thermophila
NADPH
-
Tetrahymena pyriformis
NADPH
-
Tetrahymena thermophila