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Literature summary for 1.2.1.3 extracted from

  • Buchman, C.D.; Hurley, T.D.
    Inhibition of the aldehyde dehydrogenase 1/2 family by psoralen and coumarin derivatives (2017), J. Med. Chem., 60, 2439-2455 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.2.1.3

Crystallization (Commentary)

Crystallization (Comment) Organism
purified enzyme in complex with inhibitor 2, X-ray diffraction structure determination and analysis at 2.4 A resolution Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
2,3,5,6,9-pentamethyl-7H-furo[3,2-g][1]benzopyran-7-one 12.8% inhibition at 0.01 mM Homo sapiens
2,3,5,6-tetramethyl-7H-furo[3,2-g][1]benzopyran-7-one 80.5% inhibition at 0.01 mM Homo sapiens
2,3,5-trimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one 98.5% inhibition at 0.01 mM Homo sapiens
2,3,5-trimethyl-6-[3-oxo-3-(piperidin-1-yl)propyl]-7H-furo[3,2-g][1]benzopyran-7-one competitve, 96.2% inhibition at 0.01 mM Homo sapiens
2,3-dimethyl-5-propyl-7H-furo[3,2-g][1]benzopyran-7-one 76.2% inhibition at 0.01 mM Homo sapiens
2-[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]acetamide 10.5 inhibition at 0.01 mM Homo sapiens
3,4,10-trimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-2,6-dione 19.8% inhibition at 0.01 mM Homo sapiens
3,4,8,9-tetramethyl-7H-furo[2,3-f][1]benzopyran-7-one 53.6% inhibition at 0.01 mM Homo sapiens
3,4-dimethyl-6,7,8,9-tetrahydro-2H-[1]benzofuro[3,2-g][1]benzopyran-2-one 38.7% inhibition at 0.01 mM Homo sapiens
3,5-dimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one 93.75% inhibition at 0.01 mM Homo sapiens
3-(7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-3-yl)propanoic acid
-
 Homo sapiens
3-benzyl-4-methyl-2-oxo-2H-1-benzopyran-7-yl methanesulfonate
-
 Homo sapiens
3-tert-butyl-5,6-dimethyl-7H-furo[3,2-g][1]benzopyran-7-one 30.3% inhibition at 0.01 mM Homo sapiens
3-[(3-oxobutan-2-yl)oxy]-6H-dibenzo[b,d]pyran-6-one 35.6% inhibition at 0.01 mM Homo sapiens
4-methyl-7-[(3-methylbut-2-en-1-yl)oxy]-2H-1-benzopyran-2-one 6.7% inhibition at 0.01 mM Homo sapiens
4-methyl-7-[(prop-2-en-1-yl)oxy]-2H-1-benzopyran-2-one 5.4% inhibition at 0.01 mM Homo sapiens
5-benzyl-2,3-dimethyl-7H-furo[3,2-g][1]benzopyran-7-one 16.3% inhibition at 0.01 mM Homo sapiens
5-methyl-2-[(3-oxobutan-2-yl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 5.6% inhibition at 0.01 mM Homo sapiens
6-benzyl-3,5-dimethyl-7H-furo[3,2-g][1]benzopyran-7-one 16.4% inhibition at 0.01 mM; 7.2% inhibition at 0.01 mM Homo sapiens
6-bromo-3-[(1E)-N-hydroxyethanimidoyl]-2H-1-benzopyran-2-one 51.8% inhibition at 0.01 mM Homo sapiens
6-methyl-3,4-dihydro-2H,8H-benzo[1,2-b:5,4-b']dipyran-2,8-dione 74.5% inhibition at 0.01 mM Homo sapiens
7-(2-oxopropoxy)-2H-1-benzopyran-2-one 6.7% inhibition at 0.01 mM Homo sapiens
7-methoxy-4-methyl-2H-1-benzopyran-2-one 5.2% inhibition at 0.01 mM Homo sapiens
8,9-dimethyl-2,3-dihydrocyclopenta[c]furo[3,2-g][1]benzopyran-4(1H)-one 91.75% inhibition at 0.01 mM Homo sapiens
9,10-dimethyl-1,2,3,4-tetrahydro-5H-6,8-dioxacyclopenta[b]phenanthren-5-one 83.7% inhibition at 0.01 mM Homo sapiens
9,10-dimethyl-5H-6,8-dioxacyclopenta[b]phenanthren-5-one 57.8% inhibition at 0.01 mM Homo sapiens
daidzin
-
 Homo sapiens
kolaflavanone
-
 Homo sapiens
methyl 2-[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]propanoate
-
 Homo sapiens
additional information inhibition of the aldehyde dehydrogenase 1/2 family by psoralen and coumarin derivatives, structure-function relationships, overview. Poor or no inhibition by 4-methyl-7-(2-oxopropoxy)-2H-1-benzopyran-2-one, 2-[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]propanoic acid, 2H-furo[2,3-h][1]benzopyran-2-one, 4-methyl-7-(2-oxo-2-phenylethoxy)-2H-1-benzopyran-2-one, 2-[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]-N-phenylacetamide, 7-(diethylamino)-4-methyl-2H-1-benzopyran-2-one, 3-benzyl-4-methyl-2-oxo-2H-1-benzopyran-7-yl methanesulfonate, and N-(4,7-dimethyl-2-oxo-2H-1-benzopyran-6-yl)-2-methylpropanamide; inhibition of the aldehyde dehydrogenase 1/2 family by psoralen and coumarin derivatives, structure-function relationships, overview. Poor or no inhibition by 7-(diethylamino)-4-methyl-2H-1-benzopyran-2-one and 6-bromo-3-[(1E)-N-hydroxyethanimidoyl]-2H-1-benzopyran-2-one Homo sapiens
N-benzyl-3-(2,3,5-trimethyl-7-oxo-7H-furo[3,2-g][1]benzopyran-6-yl)propanamide 30.2% inhibition at 0.01 mM Homo sapiens
[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]acetonitrile 58.7% inhibition at 0.01 mM Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens P05091
-
-
Homo sapiens P30837
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
propionaldehyde + NAD+ + H2O
-
 Homo sapiens propionate + NADH + H+
-
 ?

Synonyms

Synonyms Comment Organism
Aldh1b1
-
 Homo sapiens
ALDH2
-
 Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
 assay at Homo sapiens

Cofactor

Cofactor Comment Organism Structure
NAD+
-
 Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000067
-
 pH 7.5, 25°C Homo sapiens 8,9-dimethyl-2,3-dihydrocyclopenta[c]furo[3,2-g][1]benzopyran-4(1H)-one
0.000067
-
 pH 7.5, 25°C Homo sapiens 9,10-dimethyl-1,2,3,4-tetrahydro-5H-6,8-dioxacyclopenta[b]phenanthren-5-one
0.000086
-
 pH 7.5, 25°C Homo sapiens 2,3-dimethyl-5-propyl-7H-furo[3,2-g][1]benzopyran-7-one
0.000095
-
 pH 7.5, 25°C Homo sapiens 9,10-dimethyl-1,2,3,4-tetrahydro-5H-6,8-dioxacyclopenta[b]phenanthren-5-one
0.00011
-
 pH 7.5, 25°C Homo sapiens 2,3,5-trimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one
0.00015
-
 pH 7.5, 25°C Homo sapiens 3,4,8,9-tetramethyl-7H-furo[2,3-f][1]benzopyran-7-one
0.00015
-
 pH 7.5, 25°C Homo sapiens 9,10-dimethyl-5H-6,8-dioxacyclopenta[b]phenanthren-5-one
0.00016
-
 pH 7.5, 25°C Homo sapiens 8,9-dimethyl-2,3-dihydrocyclopenta[c]furo[3,2-g][1]benzopyran-4(1H)-one
0.00019
-
 pH 7.5, 25°C Homo sapiens 2,3,5,6-tetramethyl-7H-furo[3,2-g][1]benzopyran-7-one
0.00031
-
 pH 7.5, 25°C Homo sapiens 2,3,5,6-tetramethyl-7H-furo[3,2-g][1]benzopyran-7-one
0.00034
-
 pH 7.5, 25°C Homo sapiens 3,5-dimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one
0.00036
-
 pH 7.5, 25°C Homo sapiens 2,3,5-trimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one
0.00036
-
 pH 7.5, 25°C Homo sapiens 2,3-dimethyl-5-propyl-7H-furo[3,2-g][1]benzopyran-7-one
0.00047
-
 pH 7.5, 25°C Homo sapiens 6-methyl-3,4-dihydro-2H,8H-benzo[1,2-b:5,4-b']dipyran-2,8-dione
0.00088
-
 pH 7.5, 25°C Homo sapiens 3,5-dimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one
0.0015
-
 pH 7.5, 25°C Homo sapiens methyl 2-[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]propanoate
0.002
-
 pH 7.5, 25°C Homo sapiens 2,3,5-trimethyl-6-[3-oxo-3-(piperidin-1-yl)propyl]-7H-furo[3,2-g][1]benzopyran-7-one
0.0026
-
 pH 7.5, 25°C Homo sapiens 2,3,5-trimethyl-6-[3-oxo-3-(piperidin-1-yl)propyl]-7H-furo[3,2-g][1]benzopyran-7-one
0.0035
-
 pH 7.5, 25°C Homo sapiens daidzin
0.0046
-
 pH 7.5, 25°C Homo sapiens 6-bromo-3-[(1E)-N-hydroxyethanimidoyl]-2H-1-benzopyran-2-one
0.0051
-
 pH 7.5, 25°C Homo sapiens daidzin
0.013
-
 pH 7.5, 25°C Homo sapiens 3-benzyl-4-methyl-2-oxo-2H-1-benzopyran-7-yl methanesulfonate