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Literature summary for 1.2.1.36 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 1.2.1.36

Activating Compound

Activating Compound Comment Organism Structure
7-(2-oxopropoxy)-2H-1-benzopyran-2-one activates by 6% at 0.01 mM Homo sapiens

Crystallization (Commentary)

Crystallization (Comment) Organism
purified enzyme in complex with inhibitors 2,3,5-trimethyl-6-[3-oxo-3-(piperidin-1-yl)propyl]-7H-furo[3,2-g][1]benzopyran-7-one, 7-(diethylamino)-4-methyl-2H-1-benzopyran-2-one, and 3-benzyl-4-methyl-2-oxo-2H-1-benzopyran-7-yl methanesulfonate, X-ray diffraction structure determination and analysis at 1.70-2.05 A resolution Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
2,3,5,6,9-pentamethyl-7H-furo[3,2-g][1]benzopyran-7-one 21.6% inhibition at 0.01 mM Homo sapiens
2,3,5,6-tetramethyl-7H-furo[3,2-g][1]benzopyran-7-one 9.5% inhibition at 0.01 mM Homo sapiens
2,3,5-trimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one 63.7% 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 91.3% inhibition at 0.01 mM Homo sapiens
2,3-dimethyl-5-propyl-7H-furo[3,2-g][1]benzopyran-7-one 25.9% inhibition at 0.01 mM Homo sapiens
2-[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]-N-phenylacetamide 50.4% inhibition at 0.01 mM Homo sapiens
2-[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]acetamide 71.5% inhibition at 0.01 mM Homo sapiens
2H-furo[2,3-h][1]benzopyran-2-one 39.0% inhibition at 0.01 mM Homo sapiens
3,4,10-trimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-2,6-dione 32.6% inhibition at 0.01 mM Homo sapiens
3,4,8,9-tetramethyl-7H-furo[2,3-f][1]benzopyran-7-one 38.5% 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 35.7% inhibition at 0.01 mM Homo sapiens
3,5-dimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one 51.4% inhibition at 0.01 mM Homo sapiens
3-benzyl-4-methyl-2-oxo-2H-1-benzopyran-7-yl methanesulfonate 75.4% inhibition at 0.01 mM Homo sapiens
3-tert-butyl-5,6-dimethyl-7H-furo[3,2-g][1]benzopyran-7-one 5.5% inhibition at 0.01 mM Homo sapiens
3-[(3-oxobutan-2-yl)oxy]-6H-dibenzo[b,d]pyran-6-one 41.3% inhibition at 0.01 mM Homo sapiens
4-methyl-7-(2-oxo-2-phenylethoxy)-2H-1-benzopyran-2-one 71.0% inhibition at 0.01 mM Homo sapiens
4-methyl-7-(2-oxopropoxy)-2H-1-benzopyran-2-one 47.8% inhibition at 0.01 mM Homo sapiens
4-methyl-7-[(3-methylbut-2-en-1-yl)oxy]-2H-1-benzopyran-2-one 61.7% inhibition at 0.01 mM Homo sapiens
4-methyl-7-[(prop-2-en-1-yl)oxy]-2H-1-benzopyran-2-one 64.5% inhibition at 0.01 mM Homo sapiens
5-benzyl-2,3-dimethyl-7H-furo[3,2-g][1]benzopyran-7-one 43.0% inhibition at 0.01 mM Homo sapiens
5-methyl-2-[(3-oxobutan-2-yl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 31.3% inhibition at 0.01 mM Homo sapiens
6-benzyl-3,5-dimethyl-7H-furo[3,2-g][1]benzopyran-7-one 12.6% inhibition at 0.01 mM; 41.5% inhibition at 0.01 mM Homo sapiens
6-bromo-3-[(1E)-N-hydroxyethanimidoyl]-2H-1-benzopyran-2-one
-
 Homo sapiens
6-methyl-3,4-dihydro-2H,8H-benzo[1,2-b:5,4-b']dipyran-2,8-dione 34.8% inhibition at 0.01 mM Homo sapiens
7-(2-oxopropoxy)-2H-1-benzopyran-2-one 7.6% inhibition at 0.01 mM Homo sapiens
7-(diethylamino)-4-methyl-2H-1-benzopyran-2-one 85.7% inhibition at 0.01 mM Homo sapiens
7-methoxy-4-methyl-2H-1-benzopyran-2-one 19.8% inhibition at 0.01 mM Homo sapiens
8,9-dimethyl-2,3-dihydrocyclopenta[c]furo[3,2-g][1]benzopyran-4(1H)-one 49.2% inhibition at 0.01 mM Homo sapiens
9,10-dimethyl-1,2,3,4-tetrahydro-5H-6,8-dioxacyclopenta[b]phenanthren-5-one 43.7% inhibition at 0.01 mM Homo sapiens
9,10-dimethyl-5H-6,8-dioxacyclopenta[b]phenanthren-5-one 17.6% inhibition at 0.01 mM Homo sapiens
daidzin
-
 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 daidzin, methyl 2-[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]propanoate, 2-[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]propanoic acid, 3-(7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-3-yl)propanoic acid, and 6-bromo-3-[(1E)-N-hydroxyethanimidoyl]-2H-1-benzopyran-2-one; inhibition of the aldehyde dehydrogenase 1/2 family by psoralen and coumarin derivatives, structure-function relationships, overview. Poor or no inhibition by daidzin, methyl 2-[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]propanoate, 9,10-dimethyl-1,2,3,4-tetrahydro-5H-6,8-dioxacyclopenta[b]phenanthren-5-one, and 7-(diethylamino)-4-methyl-2H-1-benzopyran-2-one; inhibition of the aldehyde dehydrogenase 1/2 family by psoralen and coumarin derivatives, structure-function relationships, overview. Poor or no inhibition by methyl 2-[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]propanoate, 7-(diethylamino)-4-methyl-2H-1-benzopyran-2-one, and 6-bromo-3-[(1E)-N-hydroxyethanimidoyl]-2H-1-benzopyran-2-one Homo sapiens
N-(4,7-dimethyl-2-oxo-2H-1-benzopyran-6-yl)-2-methylpropanamide 40.2% inhibition at 0.01 mM Homo sapiens
N-benzyl-3-(2,3,5-trimethyl-7-oxo-7H-furo[3,2-g][1]benzopyran-6-yl)propanamide 6.4% inhibition at 0.01 mM Homo sapiens
[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]acetonitrile 64.3% inhibition at 0.01 mM Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
all-trans-retinal + H2O + NAD+ Homo sapiens
-
 all-trans-retinoate + NADH + 2 H+
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens O94788
-
-
Homo sapiens P00352
-
-
Homo sapiens P47895
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
all-trans-retinal + H2O + NAD+
-
 Homo sapiens all-trans-retinoate + NADH + 2 H+
-
 ?
propionaldehyde + NAD+
-
 Homo sapiens propionate + NADH + H+
-
 ?

Synonyms

Synonyms Comment Organism
ALDH1A1
-
 Homo sapiens
Aldh1a2
-
 Homo sapiens
Aldh1a3
-
 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
0.000065
-
 pH 7.5, 25°C Homo sapiens 9,10-dimethyl-1,2,3,4-tetrahydro-5H-6,8-dioxacyclopenta[b]phenanthren-5-one
0.000069
-
 pH 7.5, 25°C Homo sapiens 2,3-dimethyl-5-propyl-7H-furo[3,2-g][1]benzopyran-7-one
0.00013
-
 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
0.00013
-
 pH 7.5, 25°C Homo sapiens 8,9-dimethyl-2,3-dihydrocyclopenta[c]furo[3,2-g][1]benzopyran-4(1H)-one
0.00013
-
 pH 7.5, 25°C Homo sapiens 9,10-dimethyl-1,2,3,4-tetrahydro-5H-6,8-dioxacyclopenta[b]phenanthren-5-one
0.00017
-
 pH 7.5, 25°C Homo sapiens 8,9-dimethyl-2,3-dihydrocyclopenta[c]furo[3,2-g][1]benzopyran-4(1H)-one
0.00027
-
 pH 7.5, 25°C Homo sapiens 2,3,5,6-tetramethyl-7H-furo[3,2-g][1]benzopyran-7-one
0.0003
-
 pH 7.5, 25°C Homo sapiens 2,3,5-trimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one
0.00033
-
 pH 7.5, 25°C Homo sapiens 2,3,5,6-tetramethyl-7H-furo[3,2-g][1]benzopyran-7-one
0.0004
-
 pH 7.5, 25°C Homo sapiens 2,3,5-trimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one
0.00076
-
 pH 7.5, 25°C Homo sapiens 3,5-dimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one
0.0011
-
 pH 7.5, 25°C Homo sapiens 3,5-dimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one
0.0016
-
 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
0.0045
-
 pH 7.5, 25°C Homo sapiens daidzin
0.01
-
 pH 7.5, 25°C Homo sapiens 3-benzyl-4-methyl-2-oxo-2H-1-benzopyran-7-yl methanesulfonate
0.011
-
 pH 7.5, 25°C Homo sapiens 3-benzyl-4-methyl-2-oxo-2H-1-benzopyran-7-yl methanesulfonate
0.014
-
 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