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Literature summary extracted from

  • Saavedra, O.M.; Isakovic, L.; Llewellyn, D.B.; Zhan, L.; Bernstein, N.; Claridge, S.; Raeppel, F.; Vaisburg, A.; Elowe, N.; Petschner, A.J.; Rahil, J.; Beaulieu, N.; MacLeod, A.R.; Delorme, D.; Besterman, J.M.; Wahhab, A.
    SAR around (L)-S-adenosyl-L-homocysteine, an inhibitor of human DNA methyltransferase (DNMT) enzymes (2009), Bioorg. Med. Chem. Lett., 19, 2747-2751.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.1.1.37 expressed in High Five insect cells Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.1.1.37 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
-
 Homo sapiens
2.1.1.37 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
-
 Homo sapiens
2.1.1.37 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-iodo-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
-
 Homo sapiens
2.1.1.37 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-methoxy-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
-
 Homo sapiens
2.1.1.37 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-methyl-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
-
 Homo sapiens
2.1.1.37 2-amino-4-[([(2S,3S,4R,5R)-5-[6-amino-2-(methylsulfanyl)-9H-purin-9-yl]-3,4-dihydroxytetrahydrofuran-2-yl]methyl)sulfanyl]butanoic acid
-
 Homo sapiens
2.1.1.37 additional information not inhibited by 0.045 mM 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-methoxy-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid Homo sapiens
2.1.1.37 S-(1-deazaadenosyl)-L-homocysteine
-
 Homo sapiens
2.1.1.37 S-(3-deazaadenosyl)-L-homocysteine
-
 Homo sapiens
2.1.1.37 S-(8-azaadenosyl)-L-homocysteine
-
 Homo sapiens
2.1.1.37 S-(N-(2-biphenyl-4-ylethyl)-2-chloroadenosyl)-L-homocysteine
-
 Homo sapiens
2.1.1.37 S-(N-(2-biphenyl-4-ylethyl)adenosyl)-L-homocysteine
-
 Homo sapiens
2.1.1.37 S-(N-(3,5-dimethoxybenzyl)adenosyl)-L-homocysteine
-
 Homo sapiens
2.1.1.37 S-(N-(pyridin-4-ylmethyl)adenosyl)-L-homocysteine
-
 Homo sapiens
2.1.1.37 S-(N-benzyladenosyl)-L-homocysteine
-
 Homo sapiens
2.1.1.37 S-(N-phenyladenosyl)-L-homocysteine
-
 Homo sapiens
2.1.1.37 S-(N-phenylethyladenosyl)-L-homocysteine
-
 Homo sapiens
2.1.1.37 S-(N-phenylpropyladenosyl)-L-homocysteine
-
 Homo sapiens
2.1.1.37 S-adenosyl-L-homocysteine
-
 Homo sapiens
2.1.1.37 S-inosinylhomocysteine
-
 Homo sapiens
2.1.1.37 S-nebularinehomocysteine
-
 Homo sapiens
2.1.1.37 S-Tubercidinylhomocysteine
-
 Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.1.1.37 S-adenosyl-L-methionine + DNA Homo sapiens the enzyme catalyzes the transfer of a methyl group from S-adenosyl-L-methionine onto the 5'-position of the cytosine ring of the DNA S-adenosyl-L-homocysteine + DNA containing 5-methylcytosine
-
 ?
2.1.1.37 S-adenosyl-L-methionine + DNA Homo sapiens the enzyme catalyzes the transfer of a methyl group from S-adenosyl-L-methionine onto the 5‘ position of the cytosine ring of the DNA S-adenosyl-L-homocysteine + DNA containing 5-methylcytosine
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.1.1.37 Homo sapiens P26358
-
-
2.1.1.37 Homo sapiens Q9UBC3
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.1.1.37 Hitrap SP-Sepharose column chromatography Homo sapiens
2.1.1.37 Q-Sepharose column chromatography and Hitrap heparin column chromatography Homo sapiens

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.1.1.37 S-adenosyl-L-methionine + DNA the enzyme catalyzes the transfer of a methyl group from S-adenosyl-L-methionine onto the 5'-position of the cytosine ring of the DNA Homo sapiens S-adenosyl-L-homocysteine + DNA containing 5-methylcytosine
-
 ?
2.1.1.37 S-adenosyl-L-methionine + DNA the enzyme catalyzes the transfer of a methyl group from S-adenosyl-L-methionine onto the 5‘ position of the cytosine ring of the DNA Homo sapiens S-adenosyl-L-homocysteine + DNA containing 5-methylcytosine
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.1.1.37 DNA methyltransferase
-
 Homo sapiens
2.1.1.37 DNMT
-
 Homo sapiens
2.1.1.37 Dnmt1 isoform Homo sapiens
2.1.1.37 DNMT3b2 isoform Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.1.1.37 0.0003
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-adenosyl-L-homocysteine
2.1.1.37 0.0003
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-Tubercidinylhomocysteine
2.1.1.37 0.0006
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-phenylpropyladenosyl)-L-homocysteine
2.1.1.37 0.0006
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(2-biphenyl-4-ylethyl)adenosyl)-L-homocysteine
2.1.1.37 0.0009
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(3,5-dimethoxybenzyl)adenosyl)-L-homocysteine
2.1.1.37 0.001
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-methyl-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
2.1.1.37 0.001
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-benzyladenosyl)-L-homocysteine
2.1.1.37 0.0015
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-Tubercidinylhomocysteine
2.1.1.37 0.002
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-adenosyl-L-homocysteine
2.1.1.37 0.002
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-phenyladenosyl)-L-homocysteine
2.1.1.37 0.002
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-phenylethyladenosyl)-L-homocysteine
2.1.1.37 0.0025
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
2.1.1.37 0.0029
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
2.1.1.37 0.003
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(8-azaadenosyl)-L-homocysteine
2.1.1.37 0.0036
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(pyridin-4-ylmethyl)adenosyl)-L-homocysteine
2.1.1.37 0.0054
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(2-biphenyl-4-ylethyl)adenosyl)-L-homocysteine
2.1.1.37 0.006
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-methyl-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
2.1.1.37 0.0067
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(2-biphenyl-4-ylethyl)-2-chloroadenosyl)-L-homocysteine
2.1.1.37 0.0068
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(3-deazaadenosyl)-L-homocysteine
2.1.1.37 0.0068
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
2.1.1.37 0.0074
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-phenylpropyladenosyl)-L-homocysteine
2.1.1.37 0.008
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 8-aza-S-adenosyl-L-homocysteine
2.1.1.37 0.018
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(3,5-dimethoxybenzyl)adenosyl)-L-homocysteine
2.1.1.37 0.021
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-iodo-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
2.1.1.37 0.022
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(pyridin-4-ylmethyl)adenosyl)-L-homocysteine
2.1.1.37 0.027
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-phenylethyladenosyl)-L-homocysteine
2.1.1.37 0.028
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-nebularinehomocysteine
2.1.1.37 0.029
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-(2-biphenyl-4-ylethyl)-2-chloroadenosyl)-L-homocysteine
2.1.1.37 0.045
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 3-deaza-S-adenosyl-L-homocysteine
2.1.1.37 0.045
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 1-deaza-S-adenosyl-L-homocysteine
2.1.1.37 0.045
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(1-deazaadenosyl)-L-homocysteine
2.1.1.37 0.0572
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
2.1.1.37 0.061
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-benzyladenosyl)-L-homocysteine
2.1.1.37 0.075
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-methoxy-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
2.1.1.37 0.154
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-(N-phenyladenosyl)-L-homocysteine
2.1.1.37 0.216
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-[([(2S,3S,4R,5R)-5-[6-amino-2-(methylsulfanyl)-9H-purin-9-yl]-3,4-dihydroxytetrahydrofuran-2-yl]methyl)sulfanyl]butanoic acid
2.1.1.37 0.256
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-([[(2S,3S,4R,5R)-5-(6-amino-2-iodo-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl]sulfanyl)butanoic acid
2.1.1.37 0.3
-
 isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-nebularinehomocysteine
2.1.1.37 0.5
-
 isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens 2-amino-4-[([(2S,3S,4R,5R)-5-[6-amino-2-(methylsulfanyl)-9H-purin-9-yl]-3,4-dihydroxytetrahydrofuran-2-yl]methyl)sulfanyl]butanoic acid
2.1.1.37 1
-
 IC50 above 1 mM, isoform DNMT1, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-inosinylhomocysteine
2.1.1.37 1
-
 IC50 above 1 mM, isoform DNMT3b2, in 50 mM Tris-HCl pH 7.6, 5% (v/v) glycerol, 1 mM EDTA, 0.1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 37°C Homo sapiens S-inosinylhomocysteine