1.2.1.3: aldehyde dehydrogenase (NAD+)
This is an abbreviated version!
For detailed information about aldehyde dehydrogenase (NAD+), go to the full flat file.
Word Map on EC 1.2.1.3
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1.2.1.3
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aldhs
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retinoic
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metastasis
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self-renewal
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isozymes
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stem-like
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smoke
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esophageal
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drinker
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nanog
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flush
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myocardial
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east
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retinaldehyde
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tumorigenic
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clinicopathological
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case-control
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smoking
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colorectal
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epithelial-mesenchymal
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cyp2e1
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chemoresistance
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spheroid
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alcohol-induced
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disulfiram
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mesenchymal
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alcohol-related
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sphere
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detoxify
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habit
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nitroglycerin
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cell-like
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4-hydroxy-2-nonenal
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tumor-initiating
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trinitrate
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mammosphere
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keratocytes
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csc-like
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sphere-forming
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cyanamide
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aerodigestive
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non-drinkers
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epcam
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glyceryl
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alcohol-dependent
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tumorsphere
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chloral
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analysis
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dehydrogenase-1
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synthesis
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low-km
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medicine
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ichthyosis
- 1.2.1.3
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aldhs
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retinoic
- metastasis
-
self-renewal
- isozymes
-
stem-like
-
smoke
- esophageal
-
drinker
-
nanog
-
flush
- myocardial
-
east
- retinaldehyde
-
tumorigenic
-
clinicopathological
-
case-control
-
smoking
- colorectal
-
epithelial-mesenchymal
- cyp2e1
-
chemoresistance
-
spheroid
-
alcohol-induced
- disulfiram
- mesenchymal
-
alcohol-related
-
sphere
-
detoxify
-
habit
- nitroglycerin
-
cell-like
- 4-hydroxy-2-nonenal
-
tumor-initiating
- trinitrate
-
mammosphere
- keratocytes
-
csc-like
-
sphere-forming
- cyanamide
-
aerodigestive
-
non-drinkers
- epcam
-
glyceryl
-
alcohol-dependent
-
tumorsphere
- chloral
- analysis
-
dehydrogenase-1
- synthesis
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low-km
- medicine
- ichthyosis
Reaction
Synonyms
ADH, AdhE, AHD-M1, ALD1A1, ALD4, ALD6, ALDDH, aldehyde dehydrogenase, aldehyde dehydrogenase (NAD), aldehyde dehydrogenase 1, aldehyde dehydrogenase 16, aldehyde dehydrogenase 1A1, aldehyde dehydrogenase 1A3, aldehyde dehydrogenase 1B1, aldehyde dehydrogenase 2, aldehyde dehydrogenase 3A1, aldehyde dehydrogenase 6, aldehyde dehydrogenase 7A1, aldehyde dehydrogenase class 1, aldehyde dehydrogenase type 2, Aldehyde dehydrogenase [NAD+], Aldehyde dehydrogenase, cytosolic, Aldehyde dehydrogenase, microsomal, aldehyde dehydrogenase-2, aldehyde dehydrogenase7, aldehyde:NAD+ oxidoreductase, ALDH, ALDH 2, ALDH I, ALDH II, ALDH-2, ALDH-E1, ALDH-E2, ALDH1, ALDH1-NL, ALDH16, ALDH1A1, Aldh1a2, Aldh1a3, Aldh1a7, Aldh1b1, ALDH2, ALDH2(1), ALDH2(2), ALDH2(3), ALDH22A1, ALDH2B8, ALDH2C4, ALDH3A1, ALDH3A2, Aldh3b1, ALDH3H1, ALDH3I1, ALDH5A, ALDH7, Aldh7a1, ALDH7B4, Aldh8a1, ALDHI, ALDHTt, ALDHX, ALHDII, Allergen Alt a 10, aryl-aldehyde dehydrogenases, BADH, benzaldehyde dehydrogenase, Brassica turgor-responsive/drought-induced gene 26 protein, Bt-Aldh, Btg-26, class 1 aldehyde dehydrogenase, class 2 aldehyde dehydrogenase, class I ALDH, CoA-independent aldehyde dehydrogenase, coniferyl-aldehyde dehydrogenase, Cphy_1178, EC 1.1.1.70, ETA-crystallin, FeaB-K-12, gamma-aminobutyraldehyde dehydrogenase, hALDH2, HsALDH16A1, irreversible NAD+-dependent aldehyde dehydrogenase, K(+)-ACDH, K(+)-activated acetaldehyde dehydrogenase, KGSADH, LsALDH16, m-methylbenzaldehyde dehydrogenase, Matured fruit 60 kDa protein, MF-60, Mg(2+)-ACDH, Mg(2+)-activated acetaldehyde dehydrogenase, mitochondrial aldehyde dehydrogenase, More, NAD+-dependent aldehyde dehydrogenase, NAD+-dependent ALDH, NAD+-linked aldehyde dehydrogenase, NAD+-pimelic semialdehyde-dependent aldehyde dehydrogenase, NAD+-specific ALDH, NAD-aldehyde dehydrogenase, NAD-dependent 4-hydroxynonenal dehydrogenase, NAD-dependent aldehyde dehydrogenase, NAD-linked aldehyde dehydrogenase, Non-lens ALDH1, p-ALDH2, P51, phenylacetaldehyde dehydrogenase, PhnN, phnY, phosphonoacetaldehyde dehydrogenase, phosphonoacetaldehyde oxidase, PM-ALDH9, PnAA dehydrogenase, propionaldehyde dehydrogenase, PuuC, R-aminobutyraldehyde dehydrogenase, RALDH, RALDH(II), RalDH1, Retinal dehydrogenase, retinal dehydrogenase type I, sALDH, salvery aldehyde dehydrogenase, ThnG, TTC0513, Turgor-responsive protein 26G, yALDH, YneI
ECTree
1.2.1.3 aldehyde dehydrogenase (NAD+)Advanced search results
results (
results (Inhibitors
Inhibitors on EC 1.2.1.3 - aldehyde dehydrogenase (NAD+)
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INHIBITOR 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
IMAGE
2,3,5,6,9-pentamethyl-7H-furo[3,2-g][1]benzopyran-7-one
12.8% inhibition at 0.01 mM
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2,3,5,6-tetramethyl-7H-furo[3,2-g][1]benzopyran-7-one
80.5% inhibition at 0.01 mM
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2,3,5-trimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one
98.5% inhibition at 0.01 mM
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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
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2,3-dimethyl-5-propyl-7H-furo[3,2-g][1]benzopyran-7-one
76.2% inhibition at 0.01 mM
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2,6-Dichloro-4-nitrophenol
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primarily inhibits isoform ALDH2 (non-competitive), but does not affect isoform ALDH3A1
2-[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]acetamide
10.5 inhibition at 0.01 mM
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3,4,10-trimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-2,6-dione
19.8% inhibition at 0.01 mM
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3,4,8,9-tetramethyl-7H-furo[2,3-f][1]benzopyran-7-one
53.6% inhibition at 0.01 mM
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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
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3,5-dimethyl-6-propyl-7H-furo[3,2-g][1]benzopyran-7-one
93.75% inhibition at 0.01 mM
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3-(7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-3-yl)propanoic acid
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3-tert-butyl-5,6-dimethyl-7H-furo[3,2-g][1]benzopyran-7-one
30.3% inhibition at 0.01 mM
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3-[(3-oxobutan-2-yl)oxy]-6H-dibenzo[b,d]pyran-6-one
35.6% inhibition at 0.01 mM
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4-amino-4-methyl-pent-2-ynthioic acid S-methylester
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i.e. ampal thiolester, inhibits ALDH1 activity in ALDH1-transfected L1210T cells resistant to hydroperoxycyclophosphamide
4-dimethylamino-4-methyl-pent-2-ynthioic acid S-methylester
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competitive, 0.4 mM, 30 min, 80% inhibition
4-hydroxy-2-nonenal
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4-hydroxy-2-nonenal completely inactivates ALDH2 activity in vitro at 100 mM
4-methyl-4-morpholin-4-yl-pent-2-ynthioic acid S-methylester
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0.6 mM, 60 min, 15% inhibition
4-methyl-7-[(3-methylbut-2-en-1-yl)oxy]-2H-1-benzopyran-2-one
6.7% inhibition at 0.01 mM
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4-methyl-7-[(prop-2-en-1-yl)oxy]-2H-1-benzopyran-2-one
5.4% inhibition at 0.01 mM
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4-tetramethylammonium-4-methyl-pent-2-ynthioic acid S-methylester
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0.6 mM, 60 min, 15% inhibition
5-benzyl-2,3-dimethyl-7H-furo[3,2-g][1]benzopyran-7-one
16.3% inhibition at 0.01 mM
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5-methyl-2-[(3-oxobutan-2-yl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one
5.6% inhibition at 0.01 mM
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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
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6-bromo-3-[(1E)-N-hydroxyethanimidoyl]-2H-1-benzopyran-2-one
51.8% inhibition at 0.01 mM
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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
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7-(2-oxopropoxy)-2H-1-benzopyran-2-one
6.7% inhibition at 0.01 mM
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7-methoxy-4-methyl-2H-1-benzopyran-2-one
5.2% inhibition at 0.01 mM
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8,9-dimethyl-2,3-dihydrocyclopenta[c]furo[3,2-g][1]benzopyran-4(1H)-one
91.75% inhibition at 0.01 mM
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8-[[4-(3-furoyl)-1-piperazinyl]methyl]-1,3-dimethyl-7-(3-methylbutyl)-3,7-dihydro-1H-purine-2,6-dione
i.e. CM026
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9,10-dimethyl-1,2,3,4-tetrahydro-5H-6,8-dioxacyclopenta[b]phenanthren-5-one
83.7% inhibition at 0.01 mM
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9,10-dimethyl-5H-6,8-dioxacyclopenta[b]phenanthren-5-one
57.8% inhibition at 0.01 mM
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adenosine 5'-monophosphate
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competitive with NAD+ and noncompetitive with acetaldehyde
arsenite
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47% residual activity at 1 mM arsenite at pH 9.5, 28% residual activity at 2 mM arsenite at pH 7.4
c-Jun N-terminal protein kinase
incubation with catalytically active JNK leads to significant inhibition of ALDH2 activity. CCl4 exposure activates JNK which translocates to mitochondria and phosphorylates ALDH2 contributing to inhibition of ALDH2 activity
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Chlorpropamide
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this inhibition may play a role in cataract formation in patients maintained on systemic corticosteroids and in tablet-dependent diabetics
cyclohexanal
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substrate inhibition at elevated aldehyde concentration, increase of NAD+ concentration from 0.85 mM to 2.55 mM removes substrate inhibition
deoxycorticosterone
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this inhibition may play a role in cataract formation in patients maintained on systemic corticosteroids and in tablet-dependent diabetics
diethylaminobenzaldehyde
0.025 mM diethylaminobenzaldehyde inhibits about 80% of the enzymatic activity
Indole-3-acetaldehyde
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substrate inhibition at elevated aldehyde concentration, increase of NAD+ concentration from 0.85 mM to 2.55 mM removes substrate inhibition
molinate sulfoxide
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i.e. S-ethyl-hexahydro-1H-azepine-1-carbothioate sulfoxide, irreversible inhibition of ALDH2
N-(2-(trifluoromethyl)benzyl)-N-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(4-(4-isopropylbenzoyl)piperazin-1-yl)propanamide
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N-(2-chlorobenzyl)-N-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(4-(4-isopropylbenzoyl)piperazin-1-yl)propanamide
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N-(2-fluorobenzyl)-N-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(4-(4-isopropylbenzoyl)piperazin-1-yl)propanamide
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N-(2-methoxybenzyl)-N-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(4-(4-isopropylbenzoyl)piperazin-1-yl)propanamide
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N-(2-methylbenzyl)-N-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(4-(4-isopropylbenzoyl)piperazin-1-yl)propanamide
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N-(3-(trifluoromethyl)benzyl)-N-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(4-(4-isopropylbenzoyl)piperazin-1-yl)propanamide
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N-(3-chlorobenzyl)-N-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(4-(4-isopropylbenzoyl)piperazin-1-yl)propanamide
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N-(3-fluorobenzyl)-N-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(4-(4-isopropylbenzoyl)piperazin-1-yl)propanamide
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N-(3-methoxybenzyl)-N-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(4-(4-isopropylbenzoyl)piperazin-1-yl)propanamide
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N-(3-methylbenzyl)-N-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(4-(4-isopropylbenzoyl)piperazin-1-yl)propanamide
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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
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p-hydroxyphenylacetaldehyde
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substrate inhibition at elevated aldehyde concentration, increase of NAD+ concentration from 0.85 mM to 2.55 mM removes substrate inhibition
p-nitrophenyl pivalate
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inhibits dehydrogenase activity with propanal and D-glyceraldehyde
pivaldehyde
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substrate inhibition at elevated aldehyde concentration, increase of NAD+ concentration from 0.85 mM to 2.55 mM removes substrate inhibition
pyridine 3-aldehyde
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substrate inhibition at elevated aldehyde concentration, increase of NAD+ concentration from 0.85 mM to 2.55 mM removes substrate inhibition
[(4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy]acetonitrile
58.7% inhibition at 0.01 mM
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acetaldehyde
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0.02 mM, substrate inhibition of isoenzyme I, no inhibition of isoenzyme II and III
acetaldehyde
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acetaldehyde inhibition of the enzyme is initiated below concentrations of 0.05 mM in the presence of 0.5 mM NAD or less
Alda-1
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0.01 mM Alda-1 inhibits the apparent formaldehyde oxidation activity of the wild type enzyme by about 90%
Chloral hydrate
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competitive inhibition of hydrolysis of p-nitrophenyl acetate, mixed inhibition with p-nitrophenyl pivalate
Chloral hydrate
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inhibition of isoenzyme I and II from mitochondria and isoenzyme II from microsomes, no inhibition of isoenzyme I from microsomes
Cu2+
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0.1 mM CuSO4, 7% inhibition of microsomal enzyme, 81% inhibition of the cytosolic enzyme
Disulfiram
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inhibition of isoenzyme III, isoenzyme I is extremely sensitive, isoenzyme II is totally insensitive
Disulfiram
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at higher concentrations of propionaldehyde (0.5 and 1 mM), ALDH1B1 activity is inhibited by disulfiram, with the extent of inhibition being about 40% at 0.01 mM disulfiram
Disulfiram
0.025 mM diethylaminobenzaldehyde inhibits about 20-30% of the enzymatic activity
Disulfiram
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no effect on microsomal enzyme, complete inhibition of the cytosolic enzyme
Disulfiram
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inhibits activity of mitochondrial isoenzyme I with NAD+ and activity of isoenzyme I and II from microsomes and mitochondria with NADP+
ethanol
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chronic or binge ethanol-exposure significantly decreases ALDH1 activity via S-nitrosylation, activity is restored by addition of dithiothreitol, ALDH1 activity (using 0.015 mM propionaldehyde as a substrate) is significantly inhibited (by 61%) in chronically ethanol-fed rats
Mg2+
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wild type enzyme activity is inhibited (64%) by Mg2+ at pH 7.4, whereas the GFP-tagged enzyme activity is not affected by Mg2+
Mg2+
Mg2+ ions suppresses (R)-trans-4-hydroxy-2-nonenal oxidation by ALDH5A to a greater extent than that of (S)-trans-4-hydroxy-2-nonenal
NADH
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competitive with respect to NAD+, non-competitive with respect to acetaldehyde
NADH
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competitive with NAD+ at high and low concentrations of acetaldehyde, product inhibitor
NADH
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while acetaldehyde alone (1.6 mM) as an inhibiting factor yields a relative rate around 38% of the maximum experimental rate, the result with 0.18 mM initial NADH is 13% of the maximum experimental rate and further declines to 6.5% at 0.4 mM NADH
nitroglycerin
intravenous nitroglycerin treatment inhibits ALDH-2 activity, activity can be restored using dithiothreitol
nitroglycerin
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ALDH2 dehydrogenase activity is inhibited by about 50% by large doses of nitroglycerin
nitroglycerin
complete inhibition at 0.05 mM nitroglycerin which can be reversed by the addition of 0.4 mM dithiothreitol
nitroglycerin
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exposure of ALDH2 to nitroglycerin results in mechanism-based oxidative inactivation of the enzyme that is partially reversed by dithiothreitol
nitroglycerin
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more than half of the original activity retained in the presence of 5.5 mM and approximate 80% of the activity is lost by the addition of 11 mM nitroglycerin
p-hydroxymercuribenzoate
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0.05 mM, potent inhibition of isoenzyme I from microsomes and mitochondria, isoenzyme II from microsomes and mitochondria is less sensitive
p-nitrobenzaldehyde
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substrate inhibition at elevated aldehyde concentration, increase of NAD+ concentration from 0.85 mM to 2.55 mM removes substrate inhibition
progesterone
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this inhibition may play a role in cataract formation in patients maintained on systemic corticosteroids and in tablet-dependent diabetics
propanal
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competitive inhibition of hydrolysis of p-nitrophenyl acetate, mixed inhibition with p-nitrophenyl pivalate
additional information
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EDTA has no effect on ALDH activity
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additional information
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inclusion of protease inhibitors, 1 mM benzamidine and 1 mM phenylmethylsulfonyl fluoride, in preparation of homogenate supernatants slightly inhibit ALDH activity
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additional information
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at the lowest concentration of substrate tested (propionaldehyde 0.1 mM), ALDH1B1 is not affected by disulfiram
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additional information
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activities of isoforms ALDH2 and ALDH3A1 are unaffected by pentachlorophenol (up to a concentration of 1 mM)
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additional information
design, synthesis of 1,3-dimethylpyrimidine-2,4-diones as potent and selective aldehyde dehydrogenase 1A1 (ALDH1A1, EC 1.2.1.36) inhibitors and comparison of inhibitory activities on different ALDH isozymes, overview
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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
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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
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additional information
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at low coenzyme concentrations, below 0.005 mM, and high aldehyde concentrations substrate inhibition of oxidation rates is observed
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