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Literature summary for 1.2.1.11 extracted from

  • Thangavelu, B.; Bhansali, P.; Viola, R.E.
    Elaboration of a fragment library hit produces potent and selective aspartate semialdehyde dehydrogenase inhibitors (2015), Bioorg. Med. Chem., 23, 6622-6631 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.2.1.11

Application

Application Comment Organism
drug development ASADH family enzymes are attractive potential targets for development of antibiotics with novel modes of action Streptococcus pneumoniae
drug development ASADH family enzymes are attractive potential targets for development of antibiotics with novel modes of action Vibrio cholerae serotype O1

Inhibitors

Inhibitors Comment Organism Structure
4-([[(1S)-1-carboxy-2-hydroxyethyl]amino]methyl)benzene-1,2-dicarboxylic acid
-
 Streptococcus pneumoniae
4-([[(1S)-1-carboxy-2-hydroxyethyl]amino]methyl)benzene-1,2-dicarboxylic acid
-
 Vibrio cholerae serotype O1
4-([[(1S)-1-carboxyethyl]amino]methyl)benzene-1,2-dicarboxylic acid
-
 Streptococcus pneumoniae
4-([[(1S)-1-carboxyethyl]amino]methyl)benzene-1,2-dicarboxylic acid
-
 Vibrio cholerae serotype O1
additional information the ASADH enzyme family shares the same substrate binding and active site catalytic groups, but the enzymes from representative bacterial and fungal species show different inhibition patterns when previously screened against low molecular weight inhibitors identified from fragment library screening. ASADH inhibitor development, overview Streptococcus pneumoniae
additional information the ASADH enzyme family shares the same substrate binding and active site catalytic groups, but the enzymes from representative bacterial and fungal species show different inhibition patterns when previously screened against low molecular weight inhibitors identified from fragment library screening. ASADH inhibitor development, overview. No inhibition by 4-([[(1S)-1-carboxy-2-hydroxyethyl]amino]methyl)benzene-1,2-dicarboxylic acid, N-(4-bromobenzyl)-N-carboxyethyl-3,4-dicarboxybenzylamine , and N-(4-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine Vibrio cholerae serotype O1
N-((4-(2-benzyl)vinyl)benzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-((4-(2-benzyl)vinyl)benzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(1-naphthyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(1-naphthyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(2-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(2-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(2-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(2-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(2-naphthyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(2-naphthyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(2-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(2-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(2-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(2-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(3-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(3-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(3-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(3-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(3-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(3-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(3-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(3-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(4-(2-perfluoropropyl))-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(4-(2-perfluoropropyl))-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(4-biphenyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(4-biphenyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(4-bromobenzyl)-N-(2-carboxy)ethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(4-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(4-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(4-carboxamidebenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(4-carboxamidebenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(4-carboxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(4-carboxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(4-difluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(4-difluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(4-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(4-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(4-t-butylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(4-t-butylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(4-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(4-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(4-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(4-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-(ethylmorpholino)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-(ethylmorpholino)-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-acetal-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-acetal-N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-acetonitrile, N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-acetonitrile, N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-allyl, N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-allyl, N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-benzyl, N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-benzyl, N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-carboxyethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-carboxyethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1
N-methyl, N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Streptococcus pneumoniae
N-methyl, N-carboxymethyl-3,4-dicarboxybenzylamine
-
 Vibrio cholerae serotype O1

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
L-aspartate 4-semialdehyde + phosphate + NADP+ Streptococcus pneumoniae
-
 L-4-aspartyl phosphate + NADPH + H+
-
 r
L-aspartate 4-semialdehyde + phosphate + NADP+ Vibrio cholerae serotype O1
-
 L-4-aspartyl phosphate + NADPH + H+
-
 r

Organism

Organism UniProt Comment Textmining
Streptococcus pneumoniae
-
-
-
Vibrio cholerae serotype O1
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
L-aspartate 4-semialdehyde + phosphate + NADP+
-
 Streptococcus pneumoniae L-4-aspartyl phosphate + NADPH + H+
-
 r
L-aspartate 4-semialdehyde + phosphate + NADP+
-
 Vibrio cholerae serotype O1 L-4-aspartyl phosphate + NADPH + H+
-
 r

Synonyms

Synonyms Comment Organism
ASADH
-
 Streptococcus pneumoniae
ASADH
-
 Vibrio cholerae serotype O1
aspartate-beta-semialdehyde dehydrogenase
-
 Streptococcus pneumoniae
aspartate-beta-semialdehyde dehydrogenase
-
 Vibrio cholerae serotype O1

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
22
-
 assay at room temperature Streptococcus pneumoniae
22
-
 assay at room temperature Vibrio cholerae serotype O1

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8.6
-
 assay at Streptococcus pneumoniae
8.6
-
 assay at Vibrio cholerae serotype O1

Cofactor

Cofactor Comment Organism Structure
NADP+
-
 Streptococcus pneumoniae
NADP+
-
 Vibrio cholerae serotype O1
NADPH
-
 Streptococcus pneumoniae
NADPH
-
 Vibrio cholerae serotype O1

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.009
-
 N-(4-(2-perfluoropropyl))-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.012
-
 N-(4-biphenyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.016
-
 N-(4-t-butylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.024
-
 N-(4-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.036
-
 N-(4-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.054
-
 N-(4-difluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.057
-
 N-(4-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.063
-
 N-(4-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.072
-
 N-(4-carboxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.176
-
 N-(ethylmorpholino)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.22
-
 N-acetonitrile, N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.229
-
 N-(4-carboxamidebenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.246
-
 N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.276
-
 N-acetal-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.296
-
 4-([[(1S)-1-carboxyethyl]amino]methyl)benzene-1,2-dicarboxylic acid pH 8.6, 22°C Streptococcus pneumoniae
0.296
-
 N-methyl, N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.297
-
 N-benzyl, N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.303
-
 N-allyl, N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.324
-
 4-([[(1S)-1-carboxy-2-hydroxyethyl]amino]methyl)benzene-1,2-dicarboxylic acid pH 8.6, 22°C Streptococcus pneumoniae
0.329
-
 N-(2-naphthyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.396
-
 N-(1-naphthyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.427
-
 N-(3-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.43
-
 N-(3-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.441
-
 N-(3-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.442
-
 N-(3-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.476
-
 N-((4-(2-benzyl)vinyl)benzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.498
-
 N-acetonitrile, N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.509
-
 N-(2-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.524
-
 N-(2-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.528
-
 N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.529
-
 N-(2-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.54
-
 N-(2-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
0.608
-
 N-(4-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.609
-
 4-([[(1S)-1-carboxyethyl]amino]methyl)benzene-1,2-dicarboxylic acid pH 8.6, 22°C Vibrio cholerae serotype O1
0.628
-
 N-(4-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.629
-
 N-(4-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.634
-
 N-(4-biphenyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.635
-
 N-(4-carboxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.639
-
 N-(4-(2-perfluoropropyl))-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.648
-
 N-(4-t-butylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.649
-
 N-(4-carboxamidebenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.654
-
 4-([[(1S)-1-carboxy-2-hydroxyethyl]amino]methyl)benzene-1,2-dicarboxylic acid pH 8.6, 22°C Vibrio cholerae serotype O1
0.655
-
 N-acetal-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.663
-
 N-allyl, N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.663
-
 N-(4-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.665
-
 N-(3-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.675
-
 N-methyl, N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.678
-
 N-(3-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.684
-
 N-(3-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.69
-
 N-(3-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.692
-
 N-(ethylmorpholino)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.696
-
 N-benzyl, N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.698
-
 N-(4-difluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.708
-
 N-(2-trifluoromethoxybenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.721
-
 N-(2-methylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.724
-
 N-(2-naphthyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.727
-
 N-(2-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.737
-
 N-(2-bromobenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
0.749
-
 N-(1-naphthyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
1.1
-
 N-((4-(2-benzyl)vinyl)benzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Vibrio cholerae serotype O1
2.4
-
 N-carboxyethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
3.6
-
 N-(4-bromobenzyl)-N-(2-carboxy)ethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae
3.8
-
 N-(4-trifluoromethylbenzyl)-N-carboxymethyl-3,4-dicarboxybenzylamine pH 8.6, 22°C Streptococcus pneumoniae

General Information

General Information Comment Organism
evolution the ASADH enzyme family shares the same substrate binding and active site catalytic groups, but the enzymes from representative bacterial and fungal species show different inhibition patterns when previously screened against low molecular weight inhibitors identified from fragment library screening Streptococcus pneumoniae
evolution the ASADH enzyme family shares the same substrate binding and active site catalytic groups, but the enzymes from representative bacterial and fungal species show different inhibition patterns when previously screened against low molecular weight inhibitors identified from fragment library screening Vibrio cholerae serotype O1
metabolism aspartate-beta-semialdehyde dehydrogenase lies at the first branch point in the aspartate metabolic pathway which leads to the biosynthesis of several essential amino acids and some important metabolites. This pathway is crucial for many metabolic processes in plants and microbes like bacteria and fungi, but is absent in mammals Streptococcus pneumoniae
metabolism aspartate-beta-semialdehyde dehydrogenase lies at the first branch point in the aspartate metabolic pathway which leads to the biosynthesis of several essential amino acids and some important metabolites. This pathway is crucial for many metabolic processes in plants and microbes like bacteria and fungi, but is absent in mammals Vibrio cholerae serotype O1