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Literature summary for 2.1.1.5 extracted from

  • Jiracek, J.; Collinsova, M.; Rosenberg, I.; Budesinsky, M.; Protivinska, E.; Netusilova, H.; Garrow, T.A.
    S-alkylated homocysteine derivatives: new inhibitors of human betaine-homocysteine S-methyltransferase (2006), J. Med. Chem., 49, 3982-3989.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 2.1.1.5

Application

Application Comment Organism
analysis synthesis of a series of S-substituted derivatives of homocysteine as potential inhibitors of human recombinant BHMT, some of these compounds are very potent inhibitors, having IC50 values in the nanomolar range Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(R,S)-2-(3-amino-3-carboxy-propylsulfanyl)-benzoic acid ca. 43% inhibition at 0.02 mM Homo sapiens
(R,S)-2-amino-4-(2-carboxy-ethyldisulfanyl)-butyric acid ca. 30% inhibition at 0.02 mM Homo sapiens
(R,S)-2-amino-4-(2-carboxymethylsulfanyl-ethylsulfanyl)-butyric acid 100% inhibition at 0.02 mM, very potent inhibitor and one of the strongest ever reported Homo sapiens
(R,S)-2-amino-4-(2-carboxymethylsulfinyl-ethylsulfanyl)-butyric acid ca. 90% inhibition at 0.02 mM Homo sapiens
(R,S)-2-amino-4-(2-phosphonomethoxy-ethylsulfanyl)-butyrate ca. 26% inhibition at 0.02 mM Homo sapiens
(R,S)-2-amino-4-(3-carboxy-propylsulfanyl)-butyric acid ca. 20% inhibition at 0.02 mM Homo sapiens
(R,S)-2-amino-4-(4-carboxymethyl-benzylsulfanyl)-butyric acid ca. 10% inhibition at 0.02 mM Homo sapiens
(R,S)-2-amino-4-(4-phosphono-butylsulfanyl)-butyric acid ca. 98% inhibition at 0.02 mM Homo sapiens
(R,S)-2-amino-4-methylsulfanylmethylsulfanyl-butyric acid ca. 21% inhibition at 0.02 mM Homo sapiens
(R,S)-2-amino-4-[(phosphonomethyl-carbamoyl)-methylsulfanyl]-butyrate ca. 9% inhibition at 0.02 mM Homo sapiens
(R,S)-3-(3-amino-3-carboxy-propylsulfanyl)-benzoic acid ca. 13% inhibition at 0.02 mM Homo sapiens
(R,S)-4-(3-amino-3-carboxy-propylsulfanyl)-benzoic acid ca. 99% inhibition at 0.02 mM Homo sapiens
(R,S)-5-(3-amino-3-carboxy-propylsulfanyl)-pentanoic acid 100% inhibition at 0.02 mM, very potent inhibitor and one of the strongest ever reported, competitive inhibition with respect to betaine binding Homo sapiens
(R,S)-5-(3-amino-3-carboxy-propylsulfinyl)-pentanoic acid ca. 97% inhibition at 0.02 mM Homo sapiens
(R,S)-5-(3-amino-3-carboxy-propylsulfonyl)-pentanoic acid ca. 29% inhibition at 0.02 mM Homo sapiens
(R,S)-6-(3-amino-3-carboxy-propylsulfanyl)-hexanoic acid 100% inhibition at 0.02 mM, very potent inhibitor and one of the strongest ever reported Homo sapiens
(R,S,R,S)-2-amino-4-(2-amino-2-carboxy-ethylsulfinyl)-butyric acid ca. 10% inhibition at 0.02 mM Homo sapiens
additional information not inhibited by (R)-5-(2-amino-2-carboxy-ethylsulfanyl)-pentanoic acid, (R,S)-4-allylsulfanyl-2-amino-butyric acid and (R,S)-2-amino-4-[(phosphonomethyl-carbamoyl)-methylsulfanyl]-butyric acid ester Homo sapiens

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.008
-
 DL-homocysteine
-
 Homo sapiens
2
-
 betaine
-
 Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
betaine + DL-homocysteine
-
 Homo sapiens dimethylglycine + L-methionine
-
 r
L-homocysteine + betaine
-
 Homo sapiens L-methionine + dimethylglycine
-
 ?

Synonyms

Synonyms Comment Organism
BHMT
-
 Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000012
-
 (R,S)-5-(3-amino-3-carboxy-propylsulfanyl)-pentanoic acid
-
 Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000087
-
-
 Homo sapiens (R,S)-5-(3-amino-3-carboxy-propylsulfanyl)-pentanoic acid
0.000096
-
-
 Homo sapiens (R,S)-2-amino-4-(2-carboxymethylsulfanyl-ethylsulfanyl)-butyric acid
0.0002
-
-
 Homo sapiens (R,S)-6-(3-amino-3-carboxy-propylsulfanyl)-hexanoic acid
0.005
-
-
 Homo sapiens (R,S)-5-(3-amino-3-carboxy-propylsulfinyl)-pentanoic acid
0.0057
-
-
 Homo sapiens (R,S)-2-amino-4-(4-phosphono-butylsulfanyl)-butyric acid
0.007
-
-
 Homo sapiens (R,S)-4-(3-amino-3-carboxy-propylsulfanyl)-benzoic acid