1.1.1.2: alcohol dehydrogenase (NADP+)

This is an abbreviated version, for detailed information about alcohol dehydrogenase (NADP+), go to the full flat file.

Reaction

a primary alcohol
+
NADP+
=
an aldehyde
+
NADPH
+
H+

Synonyms

2° Adh, 3-DG-reducing enzyme, AAur_2040, ADH, ADH-1, ADH-2, ADH-I, ADH-II, ADH2, Adh319, ADH4, Adh6, AdhA, AdhB, AKR1A1, AKR1A4, alcohol dehydrogenase C, alcohol dehydrogenase [NADP(+)], Alcohol dehydrogenase [NADP+], aldehyde reductase, aldehyde reductase (NADPH2), aldehyde/ketone reductase, aldo-keto reductase, Aldo-keto reductase family 1 member A1, aldose reductase, ALDR, alipathic aldehyde reductase, ALR, ALR 1, ALR1, BdhA, bovine brain aldehyde reductase, D-glucuronate reductase, daunorubicin reductase, DRD, EhADH1, Gre2p, hexogenate dehydrogenase, high-Km aldehyde reductase, HvADH2, L-hexonate dehydrogenase, LB-RADH, LBADH, liver alcohol dehydrogenase, low-Km aldehyde reductase, mevaldate reductase, Mpd1, NADP(H)-dependent alcohol dehydrogenase, NADP-alcohol dehydrogenase, NADP-aldehyde reductase, NADP-dependent aldehyde reductase, NADP-linked aryl alcohol dehydrogenase, NADPH-aldehyde reductase, NADPH-cytochrome c reductase, NADPH-dependent aldehyde reductase, NADPH-dependent FALDR, NADPH-dependent fatty aldehyde reductase, NADPH-linked aldehyde reductase, nonspecific succinic semialdehyde reductase, Octopine dehydrogenase, putative iron alcohol dehydrogenase, PyAeADHII, rabbit kidney aldehyde-ketone reductase, RADH, ScADHVI, short-chain ADH, short-chain alcohol dehydrogenase, short-chain dehydrogenase/reductase, TBADH, TbADH1, Teth39_1597, Teth514_0564, TPN-L-hexonate dehydrogenase, TPNH-linked aldehyde reductase, TPNH-specific aldehyde reductase, triphosphopyridine nucleotide-linked aldehyde reductase, TsAdh319, Y63 protein, yeast alcohol dehydrogenase, YqhD

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.2 alcohol dehydrogenase (NADP+)

Inhibitors

Inhibitors on EC 1.1.1.2 - alcohol dehydrogenase (NADP+)

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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1H-indol-1-yl)acetic acid
-
(2,3-dihydrocyclopenta[b]indol-4(1H)-yl)acetic acid
-
(3-benzyl-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
32.8% inhibition at 0.010 mM
(3-sulfanyl-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid
-
(3-[[(2-fluorophenyl)methyl]sulfanyl]-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid
-
(3-[[2-oxo-2-(2,4,6-trimethylanilino)ethyl]sulfanyl]-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid
-
(4-oxo-3,4-dihydro-5H-pyridazino[4,5-b]indol-5-yl)acetic acid
-
(6H-indolo[2,3-b]quinoxalin-6-yl)acetic acid
-
(7H-indolo[2',3':5,6][1,2,4]triazino[2,3-a]benzimidazol-7-yl)acetic acid
-
(8-methyl-3-[[2-oxo-2-(propylamino)ethyl]sulfanyl]-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid
-
(NH4)2SO4
-
-
1,10-phenanthroline
1-(2-(bis-(4-fluorophenyl)methoxy)ethyl)-4-(3-phenyl-2-propenyl)piperazine
-
i.e. GBR13069. 0.08 mM, 61% inhibition
1-(2-diphenylmethoxyethyl)-4-(3-phenyl-2-propenyl)-piperazine
-
GBR12783, i.e. 0.08 mM, 59% inhibition
1-(4-nitrobenzyl)-3-(4-(2-morpholinoethyl) piperazin-1-yl)quinoxalin-2(1H)-one
-
23% inhibition
-
1-(4-nitrobenzyl)-3-(4-(3-(trifluoromethyl) phenyl)piperazin-1-yl) quinoxalin-2(1H)-one
-
43% inhibition
-
1-(4-nitrobenzyl)-3-(4-(4-methoxyphenyl) piperazin-1-yl)quinoxalin-2(1H)-one
-
26% inhibition
-
1-(4-nitrobenzyl)-3-(4-(pyrazin-2-yl) piperazin-1-yl)quinoxalin-2(1H)-one
-
24% inhibition
-
1-(4-nitrobenzyl)-3-styrylquinoxalin-2(1H)-one
-
30% inhibition
-
12-ketochenodeoxycholic acid
-
inhibition of the ADH from Lactobacillus brevis by bile acids, acetone prevents partially
2',5'-ADP
-
-
2,3-dimethylsuccinic acid
2,4-dimethylglutaric acid
-
-
2,5-dihydro-3H-[1,2,4]triazino[5,6-b]indole-3-thione
-
2-(2-oxo-3-phenethylquinoxalin-1(2H)-yl) acetic acid
-
-
-
2-(2-oxo-3-styrylquinoxalin-1(2H)-yl) acetic acid
-
-
-
2-(3,7-bis(4-fluorophenyl)-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
41.0% inhibition at 0.010 mM
2-(3-(2,4-difluorophenylamino)-6-nitro-2-oxoquinoxalin-1(2H)-yl) acetic acid
-
-
-
2-(3-(2,4-dihydroxyphenyl)-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
36.6% inhibition at 0.010 mM
2-(3-(3-(tert-butylamino)-3-oxoprop-1-en-1-yl)-2-oxoquinoxalin-1(2H)-yl) acetic acid
-
-
-
2-(3-(3-indolyl)-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
32.3% inhibition at 0.010 mM
2-(3-(4-(4-methoxyphenyl) piperazin-1-yl)-2-oxoquinoxalin-1(2H)-yl) acetic acid
-
-
-
2-(3-(4-bromothiophenoxy)-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
12.8% inhibition at 0.010 mM
2-(3-(4-chlorothiophenoxy)-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
42.4% inhibition at 0.010 mM
2-(3-(4-fluorophenethyl)-2-oxoquinoxalin-1(2H)-yl) acetic acid
-
-
-
2-(3-(4-fluorophenyl)-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
31.8% inhibition at 0.010 mM
2-(3-(4-fluorostyryl)-2-oxoquinoxalin-1(2H)-yl) acetic acid
-
-
-
2-(3-(4-fluorostyryl)-6-nitro-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
-
-
2-(3-(4-hydroxyphenyl)-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
34.6% inhibition at 0.010 mM
2-(3-phenoxy-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
6.6% inhibition at 0.010 mM
2-(3-phenyl-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
25.4% inhibition at 0.010 mM
2-(3-thiophenoxy-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
32.2% inhibition at 0.010 mM
2-(6-bromo-3-(2,4-dihydroxyphenyl)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
38.1% inhibition at 0.010 mM
2-(6-bromo-3-(4-bromothiophenoxy)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
8.7% inhibition at 0.010 mM
2-(6-chloro-3-(2,4-dihydroxyphenyl)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
46.5% inhibition at 0.010 mM
2-(6-chloro-3-(4-fluorostyryl)-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
-
-
2-(6-fluoro-3-(2,4-dihydroxyphenyl)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
42.5% inhibition at 0.010 mM
2-(7-(4-fluorobenzyl)-3-(2,4-dihydroxyphenyl)-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
11.6% inhibition at 0.010 mM
2-(7-bromo-3-(2,4-dihydroxyphenyl)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
35.9% inhibition at 0.010 mM
2-(7-bromo-3-(3-indolyl)-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
17.5% inhibition at 0.010 mM
2-(7-bromo-3-(4-bromothiophenoxy)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
24.0% inhibition at 0.010 mM
2-(7-bromo-3-(4-chlorothiophenoxy)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
10.2% inhibition at 0.010 mM
2-(7-chloro-2-oxo-3-styrylquinoxalin-1(2H)-yl) acetic acid
-
-
-
2-(7-chloro-3-(2,4-dihydroxyphenyl)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
44.5% inhibition at 0.010 mM
2-(7-chloro-3-(2-benzothiophene)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
53.3% inhibition at 0.010 mM
2-(7-chloro-3-(4-bromothiophenoxy)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
14.1% inhibition at 0.010 mM
2-(7-chloro-3-(4-chlorothiophenoxy)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
17.3% inhibition at 0.010 mM
2-(7-chloro-3-(4-fluorophenyl)-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
23.6% inhibition at 0.010 mM
2-(7-fluoro-3-(2,4-dihydroxyphenyl)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
46.2% inhibition at 0.010 mM
2-(7-fluoro-3-(4-bromothiophenoxy)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
45.5% inhibition at 0.010 mM
2-(7-fluoro-3-(4-chlorothiophenoxy)-2-oxoquinoxalin-1(2H)-yl)-acetic acid
-
29.5% inhibition at 0.010 mM
2-(7-fluoro-3-(4-fluorophenyl)-2-oxoquinoxalin-1(2H)-yl)acetic acid
-
35.8% inhibition at 0.010 mM
2-ethylhexanoate
-
-
2-mercaptoethanol
-
-
20alpha-hydroxysteroid dehydrogenase
-
competitive inhibition, the inhibitor forms a 10fold stronger binding interaction with the catalytic residue (Tyr55), non-conserved hydrogen bonding interaction with His222, and additional van der Waals contacts with the non-conserved C-terminal residues Leu306, Leu308 and Phe311 that contribute to the inhibitor's selectivity advantage for 20alpha-hydroxysteroid dehydrogenase over 3,5-dichlorosalicylic acid
-
3,3'-tetramethylenglutaric acid
3,3-dimethylglutaric acid
-
-
3,5-dichlorosalicylic acid
-
mixed type of competitive and non-competitive patterns with respect to the substrate. The inhibitor forms a network of hydrogen bonds with the active site residues Trp22, Tyr50, His113, Trp114 and Arg312. Is a less potent inhibitor of ALR1 (256fold) when compared to 20alpha-hydroxysteroid dehydrogenase
3-(1H-indol-1-yl)propanoic acid
-
3-(4-fluorostyryl)-1-(4-nitrobenzyl) quinoxalin-2(1H)-one
-
24% inhibition
-
3-(benzo[b] thiophen-3-yl)-1-(4-nitrobenzyl)quinoxalin-2(1H)-one
-
32% inhibition
-
3-[3-[(diethylamino)methyl]-1H-indol-1-yl]propanoic acid
-
4-carboxybenzaldehyde
-
uncompetitive substrate inhibition
4-chloromercuribenzoate
-
1 mM, complete inactivation
5,5'-dithiobis-(2-nitrobenzoate)
-
-
acetone
Ag+
-
100% inhibition
AL-1576
0.5 microM, (10 x KI), 13fold higher affinity for aldehyde reductase than for aldose reductase; 0.5 microM, (10 x KI), 13fold higher affinity for aldehyde reductase than for aldose reductase, reversible
AL1576
Alconil
Alrestatin
Amaranth
-
-
Amobarbital
-
-
Amytal
-
-
arachidonic acid
-
-
ascorbic acid
-
in 100 mM MES buffer (pH 6.5) with 200 mM NADPH, 0.25 mM decanal, and 125 microg of FALDR fusion protein. 1 mM inhibits by 24%
ATP-ribose
-
competitive inhibition
benzodiazepine
Benzoic acid
-
-
beta-mercaptoethanol
-
in 100 mM MES buffer (pH 6.5) with 200 mM NADPH, 0.25 mM decanal, and 125 microg of FALDR fusion protein. 1 mM inhibits by 25%
Blue dextran
-
-
-
Ca2+
-
26% inhibition
carbamazepine
-
-
Cd2+
1 mM, complete inhibition
chlorpromazine
chlorpromazine-HCl
-
-
cholic acid
-
inhibition of the ADH from Lactobacillus brevis by bile acids, acetone prevents partially
Chromone
-
-
Cibacron blue F3GA
Co2+
-
91% inhibition
D-glucuronate
-
high concentrations, inhibition in a non-competitive manner
diethyldicarbonate
-
kidney aldehyde reductase
diethyldithiocarbamate
-
in 100 mM MES buffer (pH 6.5) with 200 mM NADPH, 0.25 mM decanal, and 125 microg of FALDR fusion protein. 1 mM inhibits by 50%, 0.25 mM inhibits by 39%
Diphenic acid
Diphenylhydantoin
-
-
dipyridyl
-
in 100 mM MES buffer (pH 6.5) with 200 mM NADPH, 0.25 mM decanal, and 125 microg of FALDR fusion protein. 1 mM inhibits by 54%, 0.25 mM inhibits by 41%
Dithionite
-
in 100 mM MES buffer (pH 6.5) with 200 mM NADPH, 0.25 mM decanal, and 125 microg of FALDR fusion protein. 1 mM inhibits by 75%, 0.25 mM inhibits by 92%
dithiothreitol
-
in 100 mM MES buffer (pH 6.5) with 200 mM NADPH, 0.25 mM decanal, and 125 microg of FALDR fusion protein. 1 mM inhibits by 24%
Dodecanol
-
in 100 mM MES buffer (pH 6.5) with 200 mM NADPH, 0.25 mM decanal, and 125 microg of FALDR fusion protein. 1 mM inhibits by 46%, 0.25 mM inhibits by 45%
epalrestat
Ethacrynic acid
-
-
ethylphenylhydantoin
-
-
fidarestat
flunarizine
-
0.08 mM, 54% inhibition
glycerol
-
non-competitive inhibitor with D-glyceraldehyde as substrate
haematin
-
-
hydroxylamine
-
-
indigo carmine
-
-
Indocyanine green
-
-
indomethacin
-
-
iodoacetamide
iodoacetic acid
L-Gulonic acid
-
product inhibition
lidorestat
binding mode, overview
LiSO4
-
Mg2+
-
10 mM, 78% of initial activity
Mn2+
-
29% inhibition
N-(tert-butyl)-3-(4-(4-nitrobenzyl)-3-oxo-3, 4-dihydroquinoxalin-2-yl) acryl amide
-
36% inhibition
-
N-ethylmaleimide
NADP+
NADPH
NaN3
1 mM, complete loss of activity
ONO-2235
-
-
p-chloromercuribenzoate
p-hydroxymercuribenzoate
p-mercuribenzoate
phenacemide
-
-
Phenobarbital
Phenobarbitone
-
-
phenolsulfophthalein
-
-
-
Phenylmethylsulfonylfluoride
-
lower molecular weight form
phenylpyruvic acid
-
low-molecular weight aldehyde reductase, noncompetitively inhibition
ponalrestat
potassium phosphate
-
-
Procion Reed HE3B
-
-
pyrazole
pyridine 3-aldehyde
quercetin
quercetrin
-
-
Rose bengal
-
-
sodium amobarbital
-
-
Sodium barbitone
Sodium fluoride
-
-
sodium phenobarbital
sodium valproate
sorbinil
Sulfobromophthalein
-
-
Tolrestat
zopolrestat
-
-
[(5H-[1,2,4]triazino[5,6-b]indol-3-yl)sulfanyl]acetic acid
-
[2-oxo-3-(2-phenylethyl)quinoxalin-1(2H)-yl]acetic acid
-
22.0% inhibition at 0.010 mM
[2-oxo-3-[(Z)-2-phenylethenyl]quinoxalin-1(2H)-yl]acetic acid
-
32.0% inhibition at 0.010 mM
-
[3-(2,2-dimethylpropanoyl)-1H-indol-1-yl]acetic acid
-
[3-[(diethylamino)methyl]-1H-indol-1-yl]acetic acid
-
[3-[(dimethylamino)methyl]-2-methyl-1H-indol-1-yl]acetic acid
-
[3-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2-oxoquinoxalin-1(2H)-yl]acetic acid
-
32.6% inhibition at 0.010 mM
[3-[(E)-2-(4-hydroxyphenyl)ethenyl]-2-oxoquinoxalin-1(2H)-yl]acetic acid
-
42.4% inhibition at 0.010 mM
[3-[(E)-2-(4-methoxyphenyl)ethenyl]-2-oxoquinoxalin-1(2H)-yl]acetic acid
-
21.8% inhibition at 0.010 mM
[3-[(morpholin-4-yl)methyl]-1H-indol-1-yl]acetic acid
-
[3-[(propan-2-yl)sulfanyl]-5H-[1,2,4]triazino[5,6-b]indol-5-yl]acetic acid
-
[3-[(pyrrolidin-1-yl)methyl]-1H-indol-1-yl]acetic acid
-
[3-[2-(4-hydroxyphenyl)ethyl]-2-oxoquinoxalin-1(2H)-yl]acetic acid
-
12.2% inhibition at 0.010 mM
[5-(3-carboxymethoxy-4-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid
-
crystallization data. The rotameric state of the conserved residue Trp220 in aldehyde reductase ALR1, i.e Trp 219 in aldose reductase ALR2, is important in forming a pi-stacking interaction with the inhibitor in aldose reductase and contributes to the difference in the binding of the inhibitor to the enzymes; i.e. CMD, a potent inhibitor of ALR2, but not for ALR1. For binding to ALR1, the partially disordered inhibitor forms a tight network of hydrogen bonds with the active site residues Tyr50 and His113 and NADPH, structure molecular modelling, overview. The non-conserved C-terminal residue Leu300 in ALR2, which is Pro301 in ALR1, contributes to inhibitor selectivity
[5-(3-hydroxy-4-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetic acid
-
; i.e. HMD, modelling of inhibitor-enzyme active site complex
[7-fluoro-3-[(E)-2-(4-hydroxyphenyl)ethenyl]-2-oxoquinoxalin-1(2H)-yl]acetic acid
-
36.2% inhibition at 0.010 mM
[7-fluoro-3-[2-(4-hydroxyphenyl)ethyl]-2-oxoquinoxalin-1(2H)-yl]acetic acid
-
23.0% inhibition at 0.010 mM
additional information
-