Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 3.4.21.27 extracted from

  • Hangeland, J.J.; Friends, T.J.; Rossi, K.A.; Smallheer, J.M.; Wang, C.; Sun, Z.; Corte, J.R.; Fang, T.; Wong, P.C.; Rendina, A.R.; Barbera, F.A.; Bozarth, J.M.; Luettgen, J.M.; Watson, C.A.; Zhang, G.; Wei, A.; Ramamurthy, V.; Morin, P.E.; Bisacchi, G.S.; Subramaniam, S.; Arunachalam, P.; Mathur, A.; Seiffert, D.
    Phenylimidazoles as potent and selective inhibitors of coagulation factor XIa with in vivo antithrombotic activity (2014), J. Med. Chem., 57, 9915-9932.
    View publication on PubMed
Search for more literature for 3.4.21.27

Crystallization (Commentary)

Crystallization (Comment) Organism
in complaex with inhibitors, hanging drop vapor diffusion method, using 0.2 M (NH4)2SO4, 25% (w/v) polyethylene glycol methyl ether 2000, and 100 mM NaOAc, pH 4.6 Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(2,4-dibromo-3-[[(4-carbamimidamidobutyl)carbamoyl]oxy]-6-hydroxyphenyl)acetic acid
-
 Homo sapiens
(2,4-dibromo-6-[[(4-carbamimidamidobutyl)carbamoyl]oxy]-3-hydroxyphenyl)acetic acid
-
 Homo sapiens
(2S)-2-([[(1R)-1-(4-bromophenyl)ethyl]carbamoyl]amino)-N-[(2S)-1-[[(2S)-5-carbamimidamido-1-oxo-1-(1,3-thiazol-2-yl)pentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]-2-(4-hydroxyphenyl)ethanamide
-
 Homo sapiens
(2S)-2-([[(1R)-1-(4-bromophenyl)ethyl]carbamoyl]amino)-N-[(2S)-1-[[(2S)-5-carbamimidamido-1-oxo-1-(1,3-thiazol-2-yl)pentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]-2-(pyridin-3-yl)ethanamide
-
 Homo sapiens
2'-[(6-carbamimidoyl-1-ethyl-1H-indol-3-yl)methyl]-4-methyl-5'-[[(5-methylpyrazin-2-yl)methyl]carbamoyl]biphenyl-2-carboxylic acid
-
 Homo sapiens
2-(3-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)phenyl)acetic acid
-
 Homo sapiens
2-(4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)phenyl)acetic acid
-
 Homo sapiens
2-carbamimidamido-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl pyridine-3-carboxylate
-
 Homo sapiens
3'-[(2S,4R)-6-carbamimidoyl-4-methyl-4-phenyl-1,2,3,4-tetrahydroquinolin-2-yl]-4-carbamoyl-5'-[(3-methylbutanoyl)amino]biphenyl-2-carboxylic acid
-
 Homo sapiens
3-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)benzamide
-
 Homo sapiens
4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)-N,N-dimethylbenzamide
-
 Homo sapiens
4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)-N-methylbenzamide
-
 Homo sapiens
4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)benzamide
-
 Homo sapiens
4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-5-bromo-1H-imidazol-4-yl)-benzamide
-
 Homo sapiens
4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-5-chloro-1H-imidazol-4-yl)-benzamide
-
 Homo sapiens
4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-5-fluoro-1H-imidazol-4-yl)-benzamide
-
 Homo sapiens
4-(2-(S-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)benzoic acid
-
 Homo sapiens
BMS-262084
-
 Homo sapiens
ethyl 2-(3-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)phenyl)-acetate
-
 Homo sapiens
ethyl 2-(4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)phenyl)-acetate
-
 Homo sapiens
methyl 4-(2-((S)-1-(trans-4-(aminomethyl)-cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)-benzoate
-
 Homo sapiens
trans-4-(aminomethyl)-N-((S)-1-(4-(3-cyanophenyl)-1H-imidazol-2-yl)-2-phenylethyl)cyclohexanecarboxamide
-
 Homo sapiens
trans-4-(aminomethyl)-N-((S)-1-(4-(4-cyanophenyl)-1H-imidazol-2-yl)-2-phenylethyl)cyclohexanecarboxamide
-
 Homo sapiens
trans-4-(aminomethyl)-N-((S)-1-(5-oxo-1-phenyl-4,5-dihydro-1H-1,2,4-triazol-3-yl)-2-phenylethyl)cyclohexanecarboxamide
-
 Homo sapiens
trans-4-(aminomethyl)-N-((S)-2-phenyl-1-(2-phenyl-1H-imidazol-4-yl)ethyl)cyclohexanecarboxamide
-
 Homo sapiens
trans-4-(aminomethyl)-N-((S)-2-phenyl-1-(3-phenyl-1H-1,2,4-triazol-5-yl)ethyl)cyclohexanecarboxamide
-
 Homo sapiens
trans-4-(aminomethyl)-N-((S)-2-phenyl-1-(3-phenyl-1H-pyrazol-5-yl)ethyl)cyclohexanecarboxamide
-
 Homo sapiens
trans-4-(aminomethyl)-N-((S)-2-phenyl-1-(4-(4-sulfamoylphenyl)-1H-imidazol-2-yl)ethyl)cyclohexanecarboxamide
-
 Homo sapiens
trans-4-(aminomethyl)-N-((S)-2-phenyl-1-(4-phenyl-1H-imidazol-2-yl)ethyl)cyclohexanecarboxamide
-
 Homo sapiens
trans-4-(aminomethyl)-N-((S)-2-phenyl-1-(5-phenyloxazol-2-yl)ethyl)cyclohexanecarboxamide
-
 Homo sapiens
trans-N-((S)-1-(4-(3-(2-amino-2-oxoethyl)phenyl)-1H-imidazol-2-yl)-2-phenylethyl)-4-(aminomethyl)cyclohexanecarboxamide
-
 Homo sapiens
trans-N-((S)-1-(4-(3-amino-1H-indazol-6-yl)-1H-imidazol-2-yl)-2-phenylethyl)-4-(aminomethyl)cyclohexanecarboxamide
-
 Homo sapiens
trans-N-((S)-1-(4-(3-amino-1H-indazol-6-yl)-5-chloro-1H-imidazol-2-yl)-2-phenylethyl)-4-(aminomethyl)cyclohexanecarboxamide reversible enzyme inhibition Homo sapiens
trans-N-((S)-1-(4-(3-amino-1H-indazol-6-yl)-5-fluoro-1H-imidazol-2-yl)-2-phenylethyl)-4-(aminomethyl)cyclohexanecarboxamide
-
 Homo sapiens
trans-N-((S)-1-(4-(4-(2-amino-2-oxoethyl)phenyl)-1H-imidazol-2-yl)-2-phenylethyl)-4-(aminomethyl)cyclohexanecarboxamide
-
 Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
factor IX + H2O Homo sapiens
-
 factor IXa + ?
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens P03951
-
-

Purification (Commentary)

Purification (Comment) Organism
Ni-NTA column chromatography Homo sapiens

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
factor IX + H2O
-
 Homo sapiens factor IXa + ?
-
 ?

Synonyms

Synonyms Comment Organism
coagulation factor XIa
-
 Homo sapiens
FXIa
-
 Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0000002
-
 3'-[(2S,4R)-6-carbamimidoyl-4-methyl-4-phenyl-1,2,3,4-tetrahydroquinolin-2-yl]-4-carbamoyl-5'-[(3-methylbutanoyl)amino]biphenyl-2-carboxylic acid at pH 7.4 and 37°C Homo sapiens
0.0000003
-
 trans-N-((S)-1-(4-(3-amino-1H-indazol-6-yl)-5-fluoro-1H-imidazol-2-yl)-2-phenylethyl)-4-(aminomethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens
0.000003
-
 trans-N-((S)-1-(4-(3-amino-1H-indazol-6-yl)-1H-imidazol-2-yl)-2-phenylethyl)-4-(aminomethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens
0.000003
-
 trans-N-((S)-1-(4-(3-amino-1H-indazol-6-yl)-5-chloro-1H-imidazol-2-yl)-2-phenylethyl)-4-(aminomethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens
0.000004
-
 4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-5-chloro-1H-imidazol-4-yl)-benzamide at pH 7.4 and 37°C Homo sapiens
0.000009
-
 4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-5-bromo-1H-imidazol-4-yl)-benzamide at pH 7.4 and 37°C Homo sapiens
0.00003
-
 4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)benzamide at pH 7.4 and 37°C Homo sapiens
0.00003
-
 4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-5-fluoro-1H-imidazol-4-yl)-benzamide at pH 7.4 and 37°C Homo sapiens
0.00012
-
 trans-4-(aminomethyl)-N-((S)-2-phenyl-1-(4-phenyl-1H-imidazol-2-yl)ethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens
0.00015
-
 2-(4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)phenyl)acetic acid at pH 7.4 and 37°C Homo sapiens
0.00023
-
 trans-4-(aminomethyl)-N-((S)-1-(4-(4-cyanophenyl)-1H-imidazol-2-yl)-2-phenylethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens
0.000275
-
 2-(3-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)phenyl)acetic acid at pH 7.4 and 37°C Homo sapiens
0.00035
-
 4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)-N-methylbenzamide at pH 7.4 and 37°C Homo sapiens
0.0004
-
 trans-N-((S)-1-(4-(4-(2-amino-2-oxoethyl)phenyl)-1H-imidazol-2-yl)-2-phenylethyl)-4-(aminomethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens
0.000495
-
 ethyl 2-(4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)phenyl)-acetate at pH 7.4 and 37°C Homo sapiens
0.000545
-
 trans-N-((S)-1-(4-(3-(2-amino-2-oxoethyl)phenyl)-1H-imidazol-2-yl)-2-phenylethyl)-4-(aminomethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens
0.00059
-
 4-(2-(S-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)benzoic acid at pH 7.4 and 37°C Homo sapiens
0.00063
-
 ethyl 2-(3-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)phenyl)-acetate at pH 7.4 and 37°C Homo sapiens
0.0008
-
 methyl 4-(2-((S)-1-(trans-4-(aminomethyl)-cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)-benzoate at pH 7.4 and 37°C Homo sapiens
0.00098
-
 trans-4-(aminomethyl)-N-((S)-2-phenyl-1-(3-phenyl-1H-1,2,4-triazol-5-yl)ethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens
0.0011
-
 3-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)benzamide at pH 7.4 and 37°C Homo sapiens
0.00112
-
 trans-4-(aminomethyl)-N-((S)-1-(4-(3-cyanophenyl)-1H-imidazol-2-yl)-2-phenylethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens
0.00134
-
 trans-4-(aminomethyl)-N-((S)-2-phenyl-1-(4-(4-sulfamoylphenyl)-1H-imidazol-2-yl)ethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens
0.00144
-
 trans-4-(aminomethyl)-N-((S)-2-phenyl-1-(5-phenyloxazol-2-yl)ethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens
0.00164
-
 trans-4-(aminomethyl)-N-((S)-2-phenyl-1-(2-phenyl-1H-imidazol-4-yl)ethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens
0.00286
-
 4-(2-((S)-1-(trans-4-(aminomethyl)cyclohexanecarboxamido)-2-phenylethyl)-1H-imidazol-4-yl)-N,N-dimethylbenzamide at pH 7.4 and 37°C Homo sapiens
0.003074
-
 trans-4-(aminomethyl)-N-((S)-1-(5-oxo-1-phenyl-4,5-dihydro-1H-1,2,4-triazol-3-yl)-2-phenylethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens
0.00694
-
 trans-4-(aminomethyl)-N-((S)-2-phenyl-1-(3-phenyl-1H-pyrazol-5-yl)ethyl)cyclohexanecarboxamide at pH 7.4 and 37°C Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0000028
-
 at pH 7.4 and 37°C Homo sapiens BMS-262084