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1.2.1.11: aspartate-semialdehyde dehydrogenase

This is an abbreviated version!
For detailed information about aspartate-semialdehyde dehydrogenase, go to the full flat file.

Word Map on EC 1.2.1.11

Reaction

L-aspartate 4-semialdehyde
+
phosphate
 +
NADP+
=
L-4-aspartyl phosphate
 +
NADPH
 +
H+

Synonyms

AFUA_3G06830, ASA dehydrogenase, ASA DH, ASA-DH, ASADH, ASADHD, Asd, ASD enzyme, Asd1, Asd2, AsdA, aspartate beta-semialdehyde dehydrogenase, aspartate semialdehyde dehydrogenase, aspartate-beta-semialdehyde dehydrogenase, aspartate-beta-semialdeyhyde dehydrogenase, aspartate-semialdehyde dehydrogenase, aspartic acid semialdehyde dehydrogenase, aspartic beta-semialdehyde dehydrogenase, aspartic semialdehyde dehydrogenase, aspartyl beta-semialdehyde dehydrogenase, aspartyl semialdehyde dehydrogenase, BDCG_01946, CNA02450, dehydrogenase, aspartate semialdehyde, ecASADH, FtASADH, hiASADH, L-aspartate-beta-semialdehyde dehydrogenase, L-aspartate-beta-semialdehyde:NADP oxidoreductase (phosphorylating), Rv3708c

ECTree

     1 Oxidoreductases
         1.2 Acting on the aldehyde or oxo group of donors
             1.2.1 With NAD+ or NADP+ as acceptor
                1.2.1.11 aspartate-semialdehyde dehydrogenase

Inhibitors

Inhibitors on EC 1.2.1.11 - aspartate-semialdehyde dehydrogenase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R)-5-[(2-carboxyphenyl)carbamoyl]cyclohexa-3,5-diene-1,3-dicarboxylate
(1R)-5-[(3-nitrophenyl)carbamoyl]cyclohexa-3,5-diene-1,3-dicarboxylate
(1R)-5-[(4-nitrophenyl)carbamoyl]cyclohexa-3,5-diene-1,3-dicarboxylate
(2R,3aR)-5-[(methylsulfonyl)methyl]-2,3,3a,4-tetrahydro-1H-indole-2-carboxylate
(2R,5R)-2,3,4,5-tetrahydropyridine-2,5-dicarboxylate
(2R,5R)-5-nitro-2,3,4,5-tetrahydropyridine-2-carboxylate
(2R,7aR)-2,3,7,7a-tetrahydro-1H-indole-2,6-dicarboxylate
(2R,7aR)-6-hydroxy-2,3,7,7a-tetrahydro-1H-indole-2-carboxylate
(2R,7aR)-6-nitro-2,3,7,7a-tetrahydro-1H-indole-2-carboxylate
(2R,8aR)-2,7-dinitro-1,2,8,8a-tetrahydronaphthalene
(3aR)-2-oxo-2,3,3a,4-tetrahydro-1H-benzimidazole-5-carboxylic acid
(3aR)-5-nitro-1,3,3a,4-tetrahydro-2H-benzimidazol-2-one
(3aR)-5-nitro-3a,4-dihydro-1H-indene-1,3(2H)-dione
(3aR)-5-nitro-3a,4-dihydro-1H-isoindole-1,3(2H)-dione
(3aR)-6-chloro-5-nitro-3a,4-dihydro-1H-isoindole-1,3(2H)-dione
(7aR)-2-oxo-2,3,7,7a-tetrahydro-1H-indole-6-carboxylate
(7aR)-3-(carboxylatomethyl)-6-nitro-7,7a-dihydro-1H-indole-2-carboxylate
(S)-2-amino-5-fluoro-4-oxo-5-phosphono-pentanoic acid
irreversible inhibition
(S)-2-amino-5-phosphono-pent-4-ynoic acid
-
1,4-Naphthoquinone
-
-
1-amino-2-naphthol-4-sulfonic acid
-
-
-
2'-phosphoribose AMP
-
-
2,3-dichloro-1,4-naphthoquinone
-
-
2,3-dichloro-5,6-dicyano-1,4-benzoquinone
-
-
2,3-dichloro-5,8-dihydroxy-1,4-naphthoquinone
-
-
-
2-Aminoadipate
2-bromo-1,4-naphthoquinone
-
-
-
2-Chloro-1,4-naphthoquinone
-
-
2-chloro-3-methoxy-1,4-naphthoquinone
a selective, low to sub-micromolar inhibitors of the fungal ASADHs
-
3-Chloroacetylpyridine-adenine dinucleotide phosphate
-
NADP+ and NADPH protect
3-hydroxyaspartic acid
-
-
4-([[(1S)-1-carboxy-2-hydroxyethyl]amino]methyl)benzene-1,2-dicarboxylic acid
4-([[(1S)-1-carboxyethyl]amino]methyl)benzene-1,2-dicarboxylic acid
4-benzoquinone
enzyme binding structure analysis, a competitive and rel. weak inhibitor. The carbonyl oxygens of the inhibitor each participate in hydrogen bonds, one with the epsilon-nitrogen of Lys211 and the guanidine nitrogen of Arg114 (substrate binding residues), and the other with the thiol of the Cys154 nucleophile. There are also hydrophobic interactions with Asn153. While the position of these carbonyl groups are fixed, the aromatic ring adopts a somewhat different orientation in each of the subunits of the dimer
4-nitro-N,N-diethylbenzimidazolinone
4-nitro-N,N-dimethylbenzimidazolinone
4-nitro-N-ethylphthalimide
4-nitro-N-methylphthalimide
5-(carboxylatocarbonyl)-1H-pyrrole-2-carboxylate
5-aminoisoquinoline
-
-
-
5-[[(4-nitrophenyl)amino]carbonyl]-1,3-benzenedimethylcarboxylate
acetylenic and z-olefinic analogues
-
competitive inhibition
-
adenosine 5'-triphosphate
-
causes a time-dependent inactivation at a concentration of 3.5 mM, 0°C, pH 6.5 and 2 mM dithiothreitol, inactivation can be completely reversed by warming the reaction mixture to 25°C, 50% inactivation occurs at a concentration of 2.5 mM, NADH protects
aromatic aldehydes
-
e.g.: benzaldehyde, weak
catechol
-
-
caulerpin
-
molecular docking and dynamics simulation of Vibrio anguillarum aspartate semialdehyde dehydrogenase with natural product caulerpin, which binds with high energy. Caulerpin can be used as antibiotic against Vibrio anguillarum in fish aquaculture industry
cis-5-phosphonic acid pipecolic acid
-
-
cyclohexyl iodide
-
-
-
cysteine
-
in the reverse reaction
D-Cystine
-
70% inhibition at 0.01 mM, binds via the cysteine moiety covalently to the catalytic Cys135 of the enzyme, pH-dependent proces, optimal at pH 7.0-7.5, inhibition is reversible by DTT, dithioerythritol, 2-mercaptoethanol, dimercaptopropanol, and reduced glutathione, no protection by aspartate-beta-semialdehyde, NADP+ or NADPH, inhibition mechanism and kinetics
dimethyl pyridine-2,5-dicarboxylate
DTNB
-
reversible by DTT, dithioerythritol, 2-mercaptoethanol, dimercaptopropanol, and reduced glutathione
formaldehyde
-
-
Glutaraldehyde
-
-
GSSG
-
oxidized glutathione
homocysteine
-
in the reverse reaction
iodoacetamide
-
at 0.1 mM: 45.4% inactivation in the absence of NADP+, 22% inactivation in the presence of 1 mM NADP+
iodoacetate
L-2-Amino-4-oxo-5-chloropentanoic acid
L-cystine
L-cystine diethyl ester
-
68% inhibition at 0.01 mM, reversible by DTT, dithioerythritol, 2-mercaptoethanol, dimercaptopropanol, and reduced glutathione
L-cystine dimethyl ester
-
67% inhibition at 0.01 mM, reversible by DTT, dithioerythritol, 2-mercaptoethanol, dimercaptopropanol, and reduced glutathione
L-cystine hydroxamate
-
20% inhibition at 0.01 mM, reversible by DTT, dithioerythritol, 2-mercaptoethanol, dimercaptopropanol, and reduced glutathione
L-isoleucine
L-leucine
-
inhibits, when added to a final concentration of 10 mM in the assay system produces a decrease of 0.004 units in specific activity
L-lysine
L-methionine
L-threonine
methyl 5-nitropyridine-2-carboxylate
N-((4-(2-benzyl)vinyl)benzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(1-naphthyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(2-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(2-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(2-naphthyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(2-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(2-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(3-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(3-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(3-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(3-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(4-(2-perfluoropropyl))-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(4-biphenyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(4-bromobenzyl)-N-(2-carboxy)ethyl-3,4-dicarboxybenzylamine
-
-
N-(4-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(4-carboxamidebenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(4-carboxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(4-difluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(4-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(4-t-butylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(4-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(4-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-(ethylmorpholino)-N-carboxymethyl-3,4-dicarboxybenzylamine
N-acetal-N-carboxymethyl-3,4-dicarboxybenzylamine
N-acetonitrile, N-carboxymethyl-3,4-dicarboxybenzylamine
N-allyl, N-carboxymethyl-3,4-dicarboxybenzylamine
N-benzyl, N-carboxymethyl-3,4-dicarboxybenzylamine
N-carboxyethyl-3,4-dicarboxybenzylamine
N-carboxymethyl-3,4-dicarboxybenzylamine
N-ethylmaleimide
N-methyl, N-carboxymethyl-3,4-dicarboxybenzylamine
NADPH-Tris-chloride buffer
-
promotes a weak inactivation at 0°C, NADH protects
naphthalene-2,3-dialdehyde
-
-
-
p-benzoquinone
-
-
p-hydroquinone
-
-
p-hydroxymercuribenzoate
-
-
Periodate
-
-
perrhenate
-
very weak inhibitor
petrosamine B
phosphonate
-
weak inhibitor
phthalaldehyde
-
-
pipecolic acid-5-(R)-phosphate hydrochloric acid
-
-
pipecolic acid-5-(S)-phosphate hydrochloric acid
-
-
potassium phosphate
-
at a concentration of 10 mM promotes 60% inactivation at 0°C in the presence of 10 mM ATP, at a concentration of 100 mM promotes 61% inactivation in the presence of 10 mM ATP and 32% inactivation in the absence of ATP, NADH protects
S-methyl cysteine sulfoxide
inhibitor binding structure deduced from crystal structure
S-methyl-L-cysteine sulfoxide
covalently binding inhibitor via Cys134 at the active site, inactivation, inhibition and binding mechanism, reversible by addition of DTT or 2-mercaptoethanol
tellurate
-
-
tetrachloro-1,4-benzoquinone
-
-
thieno[2,3-b]thiophene-2,5-dicarboxylate
trans-5-phosphonic acid pipecolic acid
-
-
Tris salts
tungstate
-
-
additional information
-