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Literature summary extracted from

  • Brunner, K.; Steiner, E.M.; Reshma, R.S.; Sriram, D.; Schnell, R.; Schneider, G.
    Profiling of in vitro activities of urea-based inhibitors against cysteine synthases from Mycobacterium tuberculosis (2017), Bioorg. Med. Chem. Lett., 27, 4582-4587 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.5.1.47 3-[[(3,4-dichlorophenyl)carbamoyl]amino]benzoic acid inhibits both isoforms CysK1 and CysK2 and O-phosphoserine sulfhydrylase CysM Mycobacterium tuberculosis
2.5.1.47 3-[[([1,1'-biphenyl]-3-yl)carbamoyl]amino]benzoic acid inhibits both isoforms CysK1 and CysK2 and O-phosphoserine sulfhydrylase CysM Mycobacterium tuberculosis
2.5.1.47 4-[[(3,4-dichlorophenyl)carbamoyl]amino]-2-hydroxybenzoic acid selective for isoform CysK1, IC50 value for isoform CysK2 above 300 microM Mycobacterium tuberculosis
2.5.1.47 4-[[([1,1'-biphenyl]-3-yl)carbamoyl]amino]-2-hydroxybenzoic acid inhibits both isoforms CysK1 and CysK2 and O-phosphoserine sulfhydrylase CysM Mycobacterium tuberculosis
2.5.1.47 5-[[(3,4-dichlorophenyl)carbamoyl]amino]-2-hydroxybenzoic acid inhibits both isoforms CysK1 and CysK2 Mycobacterium tuberculosis
2.5.1.47 5-[[([1,1'-biphenyl]-3-yl)carbamoyl]amino]-2-hydroxybenzoic acid inhibits both isoforms CysK1 and CysK2 and O-phosphoserine sulfhydrylase CysM Mycobacterium tuberculosis
2.5.1.144 1-(3,4-dichlorophenyl)-3-[3-(1H-tetrazol-5-yl)phenyl]urea weak inhibitor Mycobacterium tuberculosis
2.5.1.144 2-[[(2,5-dimethoxyphenyl)carbamoyl]amino]benzoic acid weak inhibitor Mycobacterium tuberculosis
2.5.1.144 3-[[(3',4'-dichlorobiphenyl-3-yl)sulfonyl]amino]benzoic acid weak inhibitor Mycobacterium tuberculosis
2.5.1.144 3-[[(3,4-dichlorophenyl)carbamoyl]amino]benzoic acid
-
 Mycobacterium tuberculosis
2.5.1.144 3-[[(3-benzylphenyl)carbamoyl]amino]benzoic acid
-
 Mycobacterium tuberculosis
2.5.1.144 3-[[(4-bromophenyl)carbamoyl]amino]benzoic acid
-
 Mycobacterium tuberculosis
2.5.1.144 3-[[(4-chlorophenyl)carbamoyl]amino]benzoic acid
-
 Mycobacterium tuberculosis
2.5.1.144 3-[[(4-methylphenyl)carbamoyl]amino]benzoic acid
-
 Mycobacterium tuberculosis
2.5.1.144 4-[[(3-benzylphenyl)carbamoyl]amino]-2-hydroxybenzoic acid
-
 Mycobacterium tuberculosis
2.5.1.144 4-[[(4-bromophenyl)carbamoyl]amino]-2-hydroxybenzoic acid weak inhibitor Mycobacterium tuberculosis
2.5.1.144 5-[[(3,4-dichlorophenyl)carbamoyl]amino]-2-hydroxybenzoic acid weak inhibitor Mycobacterium tuberculosis
2.5.1.144 5-[[(3-benzylphenyl)carbamoyl]amino]-2-hydroxybenzoic acid
-
 Mycobacterium tuberculosis
2.8.5.1 2-[[(2,5-dimethoxyphenyl)carbamoyl]amino]benzoic acid
-
 Mycobacterium tuberculosis
2.8.5.1 3-[(3',4'-dichloro[1,1'-biphenyl]-3-sulfonyl)amino]benzoic acid
-
 Mycobacterium tuberculosis
2.8.5.1 3-[[(3,4-dichlorophenyl)carbamoyl]amino]benzoic acid
-
 Mycobacterium tuberculosis
2.8.5.1 3-[[(4-bromophenyl)carbamoyl]amino]benzoic acid
-
 Mycobacterium tuberculosis
2.8.5.1 3-[[(4-chlorophenyl)carbamoyl]amino]benzoic acid
-
 Mycobacterium tuberculosis
2.8.5.1 3-[[(4-methylphenyl)carbamoyl]amino]benzoic acid
-
 Mycobacterium tuberculosis
2.8.5.1 3-[[([1,1'-biphenyl]-3-yl)carbamoyl]amino]benzoic acid
-
 Mycobacterium tuberculosis
2.8.5.1 4-[[(4-bromophenyl)carbamoyl]amino]-2-hydroxybenzoic acid
-
 Mycobacterium tuberculosis
2.8.5.1 4-[[([1,1'-biphenyl]-3-yl)carbamoyl]amino]-2-hydroxybenzoic acid
-
 Mycobacterium tuberculosis
2.8.5.1 5-[[(3,4-dichlorophenyl)carbamoyl]amino]-2-hydroxybenzoic acid
-
 Mycobacterium tuberculosis
2.8.5.1 5-[[([1,1'-biphenyl]-3-yl)carbamoyl]amino]-2-hydroxybenzoic acid
-
 Mycobacterium tuberculosis
2.8.5.1 N-(3,4-dichlorophenyl)-N'-[3-(1H-tetrazol-5-yl)phenyl]urea
-
 Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.144 O-acetyl-L-serine + thiosulfate Mycobacterium tuberculosis
-
 S-sulfo-L-cysteine + acetate
-
 ?
2.8.5.1 3-phospho-L-serine + thiosulfate Mycobacterium tuberculosis
-
 S-sulfo-L-cysteine + phosphate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.47 Mycobacterium tuberculosis Q79FV4 isoform CysK2
-
2.5.1.47 Mycobacterium tuberculosis ATCC 25618 Q79FV4 isoform CysK2
-
2.5.1.144 Mycobacterium tuberculosis
-
-
-
2.8.5.1 Mycobacterium tuberculosis
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.144 O-acetyl-L-serine + thiosulfate
-
 Mycobacterium tuberculosis S-sulfo-L-cysteine + acetate
-
 ?
2.8.5.1 3-phospho-L-serine + thiosulfate
-
 Mycobacterium tuberculosis S-sulfo-L-cysteine + phosphate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.5.1.47 CysK2
-
 Mycobacterium tuberculosis
2.5.1.144 CysM
-
 Mycobacterium tuberculosis
2.8.5.1 CysK2
-
 Mycobacterium tuberculosis

Cofactor

EC Number Cofactor Comment Organism Structure
2.5.1.144 pyridoxal 5'-phosphate
-
 Mycobacterium tuberculosis
2.8.5.1 pyridoxal 5'-phosphate
-
 Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.5.1.47 0.0066
-
 pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis 3-[[([1,1'-biphenyl]-3-yl)carbamoyl]amino]benzoic acid
2.5.1.47 0.0101
-
 pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis 3-[[(3,4-dichlorophenyl)carbamoyl]amino]benzoic acid
2.5.1.47 0.0103
-
 pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis 5-[[([1,1'-biphenyl]-3-yl)carbamoyl]amino]-2-hydroxybenzoic acid
2.5.1.47 0.0269
-
 pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis 4-[[([1,1'-biphenyl]-3-yl)carbamoyl]amino]-2-hydroxybenzoic acid
2.5.1.47 0.0299
-
 pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis 5-[[(3,4-dichlorophenyl)carbamoyl]amino]-2-hydroxybenzoic acid
2.8.5.1 0.0066
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 3-[[([1,1'-biphenyl]-3-yl)carbamoyl]amino]benzoic acid
2.8.5.1 0.0101
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 3-[[(3,4-dichlorophenyl)carbamoyl]amino]benzoic acid
2.8.5.1 0.0103
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5-[[([1,1'-biphenyl]-3-yl)carbamoyl]amino]-2-hydroxybenzoic acid
2.8.5.1 0.013
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 3-[[(4-chlorophenyl)carbamoyl]amino]benzoic acid
2.8.5.1 0.0269
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 4-[[([1,1'-biphenyl]-3-yl)carbamoyl]amino]-2-hydroxybenzoic acid
2.8.5.1 0.0276
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 3-[[(4-bromophenyl)carbamoyl]amino]benzoic acid
2.8.5.1 0.0299
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5-[[(3,4-dichlorophenyl)carbamoyl]amino]-2-hydroxybenzoic acid