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IUBMB Comments Also acts on other short-chain secondary alcohols and, slowly, on primary alcohols.
The enzyme appears in viruses and cellular organisms
Synonyms
s-adh, isopropanol dehydrogenase, nadph-dependent primary-secondary alcohol dehydrogenase,
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isopropanol dehydrogenase
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NADPH-dependent primary-secondary alcohol dehydrogenase
ADH
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NADPH-dependent primary-secondary alcohol dehydrogenase
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NADPH-dependent primary-secondary alcohol dehydrogenase
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propan-2-ol + NADP+ = acetone + NADPH + H+
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propan-2-ol:NADP+ oxidoreductase
Also acts on other short-chain secondary alcohols and, slowly, on primary alcohols.
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4-methyl-1-pentanol + NAD+
4-methyl-1-pentanal + NADH
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?
4-methyl-1-pentanol + NADP+
4-methyl-1-pentanal + NADPH
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?
6-methyl-2-heptanol + NAD+
6-methyl-2-heptanone + NADH + H+
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6-methyl-2-heptanol + NADP+
6-methyl-2-heptanone + NADPH
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?
acetaldehyde + NADPH + H+
ethanol + NADP+
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r
acetone + NADPH + H+
propan-2-ol + NADP+
butan-2-ol + NADP+
butanone + NADPH + H+
preferred direction of the reaction is reduction rather than oxidation
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r
butanone + NADPH + H+
butan-2-ol + NADP+
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r
ethanol + NAD+
ethanal + NADH
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?
ethanol + NADP+
acetaldehyde + NADPH + H+
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r
ethanol + NADP+
ethanal + NADPH + H+
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?
pentan-2-ol + NADP+
pentan-2-one + NADPH + H+
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r
pentan-3-ol + NADP+
pentan-3-one + NADPH + H+
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r
pentan-3-one + NADPH + H+
pentan-3-ol + NADP+
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r
propan-1-ol + NADP+
propanal + NADPH + H+
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r
propan-2-ol + NAD+
acetone + NADH
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NAD+ effectively substitutes for NADP+
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?
propan-2-ol + NADP+
acetone + NADPH
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propan-2-ol + NADP+
acetone + NADPH + H+
additional information
?
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acetone + NADPH + H+
propan-2-ol + NADP+
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?
acetone + NADPH + H+
propan-2-ol + NADP+
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?
acetone + NADPH + H+
propan-2-ol + NADP+
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r
propan-2-ol + NADP+
acetone + NADPH + H+
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?
propan-2-ol + NADP+
acetone + NADPH + H+
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?
propan-2-ol + NADP+
acetone + NADPH + H+
preferred direction of the reaction is reduction rather than oxidation
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r
additional information
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also acts on short-chain secondary alcohols and, slowly, on primary alcohols
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additional information
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possibly takes part in the further metabolic reactions of the fragments formed from the side-chain of the steroid hormone precursor in the adrenals or gonads
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additional information
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enzyme transfers the pro-R hydrogen from the pyridine 4 position of the reduced coenzyme. This stereospecificity is stable over a broad range of temperatures up to 70°C and different concentrations of the coenzyme (catalytic or stoichiometric). NADP+ and its synthetic analogs, 3-acetylpyridine-ADP+ and thio-NADP+, can be used successfully
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?
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butan-2-ol + NADP+
butanone + NADPH + H+
preferred direction of the reaction is reduction rather than oxidation
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r
propan-2-ol + NADP+
acetone + NADPH + H+
preferred direction of the reaction is reduction rather than oxidation
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r
additional information
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possibly takes part in the further metabolic reactions of the fragments formed from the side-chain of the steroid hormone precursor in the adrenals or gonads
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?
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NAD+
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effectively substitutes for NADP+
additional information
no cofactor: NADH
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NADP+
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NADPH
strictly specific for NADPH
NADPH
enzyme transfers the pro-R hydrogen from the pyridine 4 position of the reduced coenzyme. This stereospecificity is stable over a broad range of temperatures up to 70°C and different concentrations of the coenzyme (catalytic or stoichiometric)
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2,2'-dipyridyl
5 mM, 80% residual activity
4-hydroxymercuribenzoic acid
0.1 mM, 49% residual activity
4-Methylpyrazole
5 mM, 68% residual activity
iodacetamide
50 mM, 49% residual activity
pyrazole
5 mM, 74% residual activity
additional information
not inhibitory: EDTA up to 5 mM
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0.00071
4-Methyl-1-pentanol
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0.00259
6-methyl-2-heptanol
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0.00028
acetaldehyde
37°C, pH 7.0
0.00078
butan-2-ol
37°C, pH 9.0
0.000061
Butanone
37°C, pH 7.0
0.0052
NADP+
pH 7.0, 37°C, cosubstrate acetone
0.51
NADPH
pH 9.0, 37°C, cosubstrate propan-2-ol
0.0056
pentan-2-ol
37°C, pH 9.0
0.0015
pentan-3-ol
37°C, pH 9.0
0.000256
pentan-3-one
37°C, pH 7.0
0.0275
propan-1-ol
37°C, pH 9.0
0.00056 - 0.00178
propan-2-ol
0.000093
acetone
37°C, pH 7.0
0.6
acetone
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at pH 7.5 and 25°C
0.00024
ethanol
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0.00056
propan-2-ol
37°C, pH 9.0
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5.5
reduction of acetone, citrate buffer
6.4 - 7
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in mitochondria
6.5 - 7.5
reduction of acetone, Bis/Tris propane buffer
8 - 8.5
oxidation of propan-2-ol, Bis/Tris propane buffer
9.5
oxidation of propan-2-ol, glycine/HCl buffer
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brenda
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brenda
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Uniprot
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putative
UniProt
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activity detected in mitochondria and cytoplasm
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brenda
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brenda
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39100
2 * 43000, SDS-PAGE, 2 * 39100, calculated
43000
2 * 43000, SDS-PAGE, 2 * 39100, calculated
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dimer
2 * 43000, SDS-PAGE, 2 * 39100, calculated
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iron limitation results in a 1.5fold increase in enzyme mRNA
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diagnostics
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characterization of adrenal and gonadal tissue
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Ploc, I.; Starka, L.
Gas chromatographic study of the histochemical reaction for isopropanol dehydrogenase
J. Chromatogr.
172
374-378
1979
Rattus norvegicus
brenda
Sutak, R.; Hrdy, I.; Dolezal, P.; Cabala, R.; Sedinova, M.; Lewin, J.; Harant, K.; Mueller, M.; Tachezy, J.
Secondary alcohol dehydrogenase catalyzes the reduction of exogenous acetone to 2-propanol in Trichomonas vaginalis
FEBS J.
279
2768-2780
2012
Trichomonas vaginalis (A2DJ40)
brenda
Peretz, M.; Bogin, O.; Keinan, E.; Burstein, Y.
Stereospecificity of hydrogen transfer by the NADP-linked alcohol dehydrogenase from the thermophilic bacterium Thermoanaerobium brockii
Int. J. Pept. Protein Res.
42
490-495
1993
Thermoanaerobacter brockii (P14941)
brenda
Koepke, M.; Gerth, M.L.; Maddock, D.J.; Mueller, A.P.; Liew, F.; Simpson, S.D.; Patrick, W.M.
Reconstruction of an acetogenic 2,3-butanediol pathway involving a novel NADPH-dependent primary-secondary alcohol dehydrogenase
Appl. Environ. Microbiol.
80
3394-3403
2014
Clostridium autoethanogenum, Clostridium autoethanogenum DSM 10061
brenda
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1.1.1.80 isopropanol dehydrogenase (NADP+)
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