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Literature summary for 3.4.22.69 extracted from

  • Shimamoto, Y.; Hattori, Y.; Kobayashi, K.; Teruya, K.; Sanjoh, A.; Nakagawa, A.; Yamashita, E.; Akaji, K.
    Fused-ring structure of decahydroisoquinoline as a novel scaffold for SARS 3CL protease inhibitor (2015), Bioorg. Med. Chem., 23, 876-890 .
    View publication on PubMed

Crystallization (Commentary)

Crystallization (Comment) Organism
crystals of the enzyme in a complex with the inhibitor (S)-2-(([(3S,4aR,8aS)-2-(4-bromobenzoyl)decahydroisoquinolin-3-yl]methyl)amino)-3-(1H-imidazol-4-yl)-propanal are obtained by co-crystallization using sitting-drop vapor diffusion at 4°C and mixing an equal volume of protein-inhibitor complex Severe acute respiratory syndrome-related coronavirus
in complex with inhibitors (2S)-2-([[(3S,4aR,8aS)-2-(biphenyl-4-ylcarbonyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-5-yl)propanal, (2S)-2-([[(3S,4aR,8aS)-2-(4-bromobenzoyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-5-yl)propanal Severe acute respiratory syndrome-related coronavirus

Inhibitors

Inhibitors Comment Organism Structure
(2S)-2-([[(3R,4aS,8aR)-2-(4-bromobenzoyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
-
Severe acute respiratory syndrome-related coronavirus
(2S)-2-([[(3R,4aS,8aR)-2-(4-fluorophenyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-5-yl)propanal
-
Severe acute respiratory syndrome-related coronavirus
(2S)-2-([[(3R,4aS,8aR)-2-([1,1'-biphenyl]-4-carbonyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
-
Severe acute respiratory syndrome-related coronavirus
(2S)-2-([[(3S,4aR,8aS)-2-(4-bromobenzoyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
-
Severe acute respiratory syndrome-related coronavirus
(2S)-2-([[(3S,4aR,8aS)-2-(4-bromobenzoyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-5-yl)propanal
-
Severe acute respiratory syndrome-related coronavirus
(2S)-2-([[(3S,4aR,8aS)-2-(4-fluorobenzoyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
-
Severe acute respiratory syndrome-related coronavirus
(2S)-2-([[(3S,4aR,8aS)-2-(biphenyl-4-ylcarbonyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-5-yl)propanal
-
Severe acute respiratory syndrome-related coronavirus
(2S)-2-([[(3S,4aR,8aS)-2-([1,1'-biphenyl]-2-carbonyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
-
Severe acute respiratory syndrome-related coronavirus
(2S)-2-([[(3S,4aR,8aS)-2-([1,1'-biphenyl]-3-carbonyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
-
Severe acute respiratory syndrome-related coronavirus
(2S)-2-([[(3S,4aR,8aS)-2-([1,1'-biphenyl]-4-carbonyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
-
Severe acute respiratory syndrome-related coronavirus
(2S)-2-([[(3S,4aR,8aS)-2-benzoyldecahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
-
Severe acute respiratory syndrome-related coronavirus
additional information the fused ring structure of the decahydroisoquinolin functions as a scaffold for SARS 3CLpro inhibitors. Interactions take place at the S1 and S2 sites, as well as additional interactions at the N-substituent of the inhibitors Severe acute respiratory syndrome-related coronavirus

Organism

Organism UniProt Comment Textmining
Severe acute respiratory syndrome-related coronavirus P0C6X7 human, i.e. SARS-CoV
-
Severe acute respiratory syndrome-related coronavirus P0C6X7 replicase polyprotein; human, i.e. SARS-CoV
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
H-Thr-Ser-Ala-Val-Leu-Gln-Ser-Gly-Phe-Arg-Lys-NH2 + H2O
-
Severe acute respiratory syndrome-related coronavirus H-Thr-Ser-Ala-Val-Leu-Gln + Ser-Gly-Phe-Arg-Lys-NH2
-
?
Thr-Ser-Ala-Val-Leu-Gln-Ser-Gly-Phe-Arg-Lys + H2O
-
Severe acute respiratory syndrome-related coronavirus Thr-Ser-Ala-Val-Leu-Gln + Ser-Gly-Phe-Arg-Lys
-
?

Synonyms

Synonyms Comment Organism
coronavirus 3C-like protease
-
Severe acute respiratory syndrome-related coronavirus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.041
-
pH 7.5, 37°C Severe acute respiratory syndrome-related coronavirus (2S)-2-([[(3S,4aR,8aS)-2-(4-bromobenzoyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
0.057
-
pH 7.5, 37°C Severe acute respiratory syndrome-related coronavirus (2S)-2-([[(3S,4aR,8aS)-2-(4-fluorobenzoyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
0.057
-
pH 7.7, 37°C Severe acute respiratory syndrome-related coronavirus (2S)-2-([[(3R,4aS,8aR)-2-(4-fluorophenyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-5-yl)propanal
0.063
-
pH 7.7, 37°C Severe acute respiratory syndrome-related coronavirus (2S)-2-([[(3S,4aR,8aS)-2-(4-bromobenzoyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-5-yl)propanal
0.068
-
pH 7.5, 37°C Severe acute respiratory syndrome-related coronavirus (2S)-2-([[(3S,4aR,8aS)-2-benzoyldecahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
0.108
-
pH 7.5, 37°C Severe acute respiratory syndrome-related coronavirus (2S)-2-([[(3S,4aR,8aS)-2-([1,1'-biphenyl]-4-carbonyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
0.108
-
pH 7.7, 37°C Severe acute respiratory syndrome-related coronavirus (2S)-2-([[(3S,4aR,8aS)-2-(biphenyl-4-ylcarbonyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-5-yl)propanal
0.135
-
pH 7.5, 37°C Severe acute respiratory syndrome-related coronavirus (2S)-2-([[(3S,4aR,8aS)-2-([1,1'-biphenyl]-3-carbonyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
0.135
-
pH 7.5, 37°C Severe acute respiratory syndrome-related coronavirus (2S)-2-([[(3S,4aR,8aS)-2-([1,1'-biphenyl]-2-carbonyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
0.175
-
pH 7.5, 37°C Severe acute respiratory syndrome-related coronavirus (2S)-2-([[(3R,4aS,8aR)-2-(4-bromobenzoyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal
0.24
-
pH 7.5, 37°C Severe acute respiratory syndrome-related coronavirus (2S)-2-([[(3R,4aS,8aR)-2-([1,1'-biphenyl]-4-carbonyl)decahydroisoquinolin-3-yl]methyl]amino)-3-(1H-imidazol-4-yl)propanal