3.4.22.B69: falcipain-2
This is an abbreviated version!
For detailed information about falcipain-2, go to the full flat file.
Word Map on EC 3.4.22.B69
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3.4.22.B69
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plasmodium
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falciparum
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antimalarial
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malaria
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hemoglobin
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falcipain-3
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antiplasmodial
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papain-family
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chloroquine-resistant
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hemoglobinases
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rhodesain
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prodomains
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plasmepsins
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hemozoin
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cruzain
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thiosemicarbazone
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chloroquine-sensitive
- 3.4.22.B69
- plasmodium
- falciparum
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antimalarial
- malaria
- hemoglobin
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falcipain-3
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antiplasmodial
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papain-family
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chloroquine-resistant
- hemoglobinases
- rhodesain
- prodomains
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plasmepsins
- hemozoin
- cruzain
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thiosemicarbazone
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chloroquine-sensitive
Reaction
The enzyme plays a key role in the hydrolysis of hemoglobin by the parasite Plasmodium falciparum. Preferred cleavage sites display arginine in P1, leucine in P2, and phenylalanine in P1' =
Synonyms
falcipain 2, falcipain-2, FP-2, Fp2, haemoglobinase
ECTree
Advanced search results
Inhibitors
Inhibitors on EC 3.4.22.B69 - falcipain-2
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(1,1-dioxido-3-oxo-1,2-benzothiazol-2(3H)-yl)(1,3,5-triaza-7-phosphatricyclo[3.3.1.13,7]decane-kappaP)gold
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24% inhibition at 0.02 mM
(4-chloro-2-trifluoromethyl-phenyl)-carbamic acid 5-methyl-2-oxo-1-[(4-oxo-pent-2-enylcarbamoyl)-methyl]-2,3-dihydro-1H-benzo[e][1,4] diazepin-3-methyl ester
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(5Z)-3-(2,4-difluorobenzyl)-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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(5Z)-3-(3-methoxybenzyl)-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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(5Z)-3-(4-fluorobenzyl)-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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(5Z)-3-(4-methylbenzyl)-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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(5Z)-3-benzyl-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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(5Z)-3-ethyl-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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(5Z)-3-methyl-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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(5Z)-3-[4-(trifluoromethyl)benzyl]-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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(S)-2-(1-(4-benzylpiperidin-1-yl)-1-oxo-3-phenylpropan-2-yl)isoindoline-1,3-dione
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(S)-2-(1-(4-benzylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)isoindoline-1,3-dione
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(S)-2-(1-(4-benzylpiperidin-1-yl)-4-methyl-1-oxopentan-2-yl)isoindoline-1,3-dione
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2,2'-((2S,2'S)-piperazine-1,4-diylbis(1-oxo-3-phenylpropane-2,1-diyl))bis(isoindoline-1,3-dione)
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2,2'-((2S,2'S)-piperazine-1,4-diylbis(3-methyl-1-oxobutane-2,1-diyl))bis(isoindoline-1,3-dione)
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2,2'-((2S,2'S)-piperazine-1,4-diylbis(4-methyl-1-oxopentane-2,1-diyl))bis(isoindoline-1,3-dione)
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2,2'-((2S,2'S,3R,3'R)-piperazine-1,4-diylbis(3-methyl-1-oxopentane-2,1-diyl))bis(isoindoline-1,3-dione)
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2-((2S,3S)-1-(4-benzylpiperidin-1-yl)-3-methyl-1-oxopentan-2-yl)isoindoline-1,3-dione
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2-[(2S)-1-(morpholin-4-yl)-1-oxo-3-phenylpropan-2-yl]-1H-isoindole-1,3(2H)-dione
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2-[(2S)-1-oxo-3-phenyl-1-(piperidin-1-yl)propan-2-yl]-1H-isoindole-1,3(2H)-dione
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2-[(2S)-1-oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-2-yl]-1H-isoindole-1,3(2H)-dione
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2-[(2S)-3-methyl-1-(morpholin-4-yl)-1-oxobutan-2-yl]-1H-isoindole-1,3(2H)-dione
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2-[(2S)-3-methyl-1-oxo-1-(piperidin-1-yl)butan-2-yl]-1H-isoindole-1,3(2H)-dione
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2-[(2S)-3-methyl-1-oxo-1-(pyrrolidin-1-yl)butan-2-yl]-1H-isoindole-1,3(2H)-dione
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2-[(2S)-4-methyl-1-(morpholin-4-yl)-1-oxopentan-2-yl]-1H-isoindole-1,3(2H)-dione
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2-[(2S)-4-methyl-1-oxo-1-(piperidin-1-yl)pentan-2-yl]-1H-isoindole-1,3(2H)-dione
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2-[(2S)-4-methyl-1-oxo-1-(pyrrolidin-1-yl)pentan-2-yl]-1H-isoindole-1,3(2H)-dione
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2-[(2S,3R)-3-methyl-1-(morpholin-4-yl)-1-oxopentan-2-yl]-1H-isoindole-1,3(2H)-dione
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2-[(2S,3R)-3-methyl-1-oxo-1-(piperidin-1-yl)pentan-2-yl]-1H-isoindole-1,3(2H)-dione
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2-[(2S,3R)-3-methyl-1-oxo-1-(pyrrolidin-1-yl)pentan-2-yl]-1H-isoindole-1,3(2H)-dione
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2-[3-(isobutylamino-methyl)-2-oxo-5-phenyl-2,3-dihydrobenzo[e][1,4]diazepin-1-yl]-N-(4-oxo-pent-2-enyl)-acetamide
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3-((2-chloro-6-methoxyquinolin-3-yl)methylene)-5-(2,4-dimethylphenyl)furan-2(3H)-one
IC50 value on parasite 0.50 microg/ml
3-((2-chloro-6-methoxyquinolin-3-yl)methylene)-5-(4-chlorophenyl)furan-2(3H)-one
IC50 value on parasite 0.61 micro/ml
3-(1-benzoyl-5-(4-flurophenyl)-4,5-dihydro-1H-pyrazol-3yl)-7-(diethyamino)-2H-chromen-2-one
3-adamantyl-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-(2-chlorophenyl)piperazin-1-yl)ethyl]-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-(3-chlorophenyl)piperazin-1-yl)ethyl]-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-(4-chlorophenyl)piperazin-1-yl)ethyl]-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-(4-cyanophenyl)piperazin-1-yl)ethyl]-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-(4-methoxyphenyl)piperazin-1-yl)ethyl]-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-cyclohexylpiperazin-1-yl)ethyl]-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-methylpiperazin-1-yl)ethyl]-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenoxypiperazin-1-yl)ethyl]-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(2,4,6-trimethoxybenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(2,4-dichlorobenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(2,4-dimethoxybenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(2,5-ditrifluoromethylbenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(2-bromobenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(2-chlorobenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(2-trifluoromethoxybenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(3,4-difluorobenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(3-carboxybenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(3-fluorobenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(3-isopropylbenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(3-methoxybenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(3-methylbenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(3-trifluoromethoxybenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(4-chlorobenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(4-fluorobenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(4-methoxybenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(4-methylbenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(4-trifluoromethoxybenzylidene)1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-(4-trifluoromethylbenzylidene)
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3-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]-5-benzylidene-1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(4-pyridylpiperazin-1-yl)ethyl]-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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3-[2-oxo-2-(piperazin-1-yl)ethyl]-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione
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3-[4-(benzylsulfamoyl)phenyl]-N-(2,3-dihydro-1,4-benzodioxin-6-yl)propanamide
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less than 5% inhibition at 0.01 mM
3-[4-[(2-phenylethyl)sulfamoyl]phenyl]-N-(5-phenyl-1,3,4-thiadiazol-2-yl)propanamide
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94.5% inhibition at 0.01 mM
3-[4-[(2-phenylethyl)sulfamoyl]phenyl]-N-(pyridin-2-ylmethyl)propanamide
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10.7% inhibition at 0.01 mM
3-[4-[(2-phenylethyl)sulfamoyl]phenyl]-N-(thiophen-2-ylmethyl)propanamide
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15.2% inhibition at 0.01 mM
3-[4-[(3-chloro-4-fluorophenyl)sulfamoyl]phenyl]-N-(2,3-dihydro-1,4-benzodioxin-6-yl)propanamide
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32.7% inhibition at 0.01 mM
3-[4-[(3-chloro-4-fluorophenyl)sulfamoyl]phenyl]-N-(5-ethyl-1,3,4-thiadiazol-2-yl)propanamide
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45.1% inhibition at 0.01 mM
amino[(2E)-2-[1-(4-methoxyphenyl)ethylidene]hydrazinyl]methanethiol
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benzyl (1-[[(2S)-2-cyanopyrrolidin-1-yl]carbonyl]cyclohexyl)carbamate
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benzyl [1-[(cyanomethyl)amino]-2-methyl-1-oxopropan-2-yl]carbamate
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chloro[N-[1-(hydroxy-kappaO)-3-methylbutan-2-yl]pyridine-2-carboxamidato(2-)-kappa2N1,N2]aurate(2-)
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43% inhibition at 0.02 mM
dichloro[3-(propan-2-yl)-2-(pyridin-2-yl-kappaN)-4,5-dihydro-1,3-oxazol-3-ium-kappaN]aurate(1-) hexafluorophosphate
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59% inhibition at 0.02 mM
heme
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heme inhibits falcipain-2 activity against both human hemoglobin and chromogenic peptide substrates through a noncompetitive-like mechanism
methyl (2E)-4-[({(3R)-3-[({[4-chloro-2-(trifluoromethyl)phenyl]carbamoyl}oxy)methyl]-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-1-yl}acetyl)amino]but-2-enoate
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N-((S)-1-(((S)-1-(((S)-1-(2-((4-fluorophenoxy)methyl)-4,5-dihydro-1H-imidazol-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)piperidine-1-carboxamide
compound inhibits the growth of the drug resistant parasite Dd2. IC50 value for strain 3D/ 0.0055 mM
N-((S)-1-(((S)-1-(((S)-2-((S)-2-((4-fluorophenoxy)methyl)pyrrolidin-1-yl)-2-oxo-1-phenylethyl)amino)-4-methyl-1-oxopentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)morpholine-4-carboxamide
compound exhibits potent anti-parasitic activity and a 7- to 12fold higher potency against drug resistant Dd2 and MCamp isolates, than the laboratory strain 3D7. IC50 value for strain 3D7 0.0009 mM
N-(1,3-benzothiazol-2-yl)-3-[4-[(2-phenylethyl)sulfamoyl]phenyl]propanamide
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41.5% inhibition at 0.01 mM
N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-[4-[(2-phenylethyl)sulfamoyl]phenyl]acetamide
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less than 5% inhibition at 0.01 mM
N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[4-[(2-phenylethyl)sulfamoyl]phenyl]propanamide
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23% inhibition at 0.01 mM
N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[4-[(3,4-dimethoxyphenyl)sulfamoyl]phenyl]propanamide
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6.3% inhibition at 0.01 mM
N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[4-[(3-methoxyphenyl)sulfamoyl]phenyl]propanamide
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17.9% inhibition at 0.01 mM
N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-[(2-phenylethyl)sulfamoyl]benzamide
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less than 5% inhibition at 0.01 mM
N-(3,4-dimethoxyphenyl)-3-[4-[(2-phenylethyl)sulfamoyl]phenyl]propanamide
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15% inhibition at 0.01 mM
N-(3-hydroxy-4-methoxyphenyl)-3-[4-[(2-phenylethyl)sulfamoyl]phenyl]propanamide
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13.6% inhibition at 0.01 mM
N-(4-oxo-pent-2-enyl)-2-(2-oxo-5-phenyl-3-morpholin-1-ylmethyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetamide
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N-(4-oxo-pent-2-enyl)-2-(2-oxo-5-phenyl-3-piperidin-1-ylmethyl-2,3-dihydro-benzo[e][1,4] diazepin-1-yl)-acetamide
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80% inhibition at 0.1 mM, no inhibition at 0.03 mM
N-(5-ethyl-1,3,4-thiadiazol-2-yl)-3-[4-[(2-phenylethyl)sulfamoyl]phenyl]propanamide
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46.5% inhibition at 0.01 mM
N-(5-ethyl-1,3,4-thiadiazol-2-yl)-3-[4-[(4-fluorophenyl)sulfamoyl]phenyl]propanamide
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72.9% inhibition at 0.01 mM
N-(cyanomethyl)-1-([[(1S,2S)-2-phenylcyclopropyl]carbonyl]amino)cyclohexanecarboxamide
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N-(cyanomethyl)-1-[(3-cyclopentylpropanoyl)amino]cyclohexanecarboxamide
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N-(cyanomethyl)-1-[(cyclopentylacetyl)amino]cyclohexanecarboxamide
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N-(cyanomethyl)-1-[[3-(2,3-dimethoxyphenyl)propanoyl]amino]cyclohexanecarboxamide
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N-(cyanomethyl)-1-[[3-(2-methoxyphenyl)propanoyl]amino]cyclohexanecarboxamide
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N-(cyanomethyl)-1-[[3-(4-methoxyphenyl)propanoyl]amino]cyclohexanecarboxamide
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N-(cyanomethyl)-1-[[3-(furan-2-yl)propanoyl]amino]cyclohexanecarboxamide
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N-(cyanomethyl)-1-[[3-(pyridin-3-yl)propanoyl]amino]cyclohexanecarboxamide
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N-(cyanomethyl)-1-[[3-(thiophen-2-yl)propanoyl]amino]cyclohexanecarboxamide
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N-[(2S)-1-[(1-cyanocyclopropyl)amino]-1-oxo-3-(pyridin-3-yl)propan-2-yl]-3-(1H-imidazol-2-yl)benzamide
P2-modified aminonitrile based inhibitor, not cytotoxic to either cancer (HeLa) or normal (Huvec) human cell lines
N-[(2S)-1-[(1-cyanocyclopropyl)amino]-1-oxo-3-(pyridin-3-yl)propan-2-yl]-3-(1H-tetrazol-1-yl)benzamide
compound shows more than 500fold selectivity for falcipain-2 over cathepsin B, K and L and about 30fold selectivity over cathepsin S. Not cytotoxic to either cancer (HeLa) or normal (Huvec) human cell lines
potassium bis(1,1-dioxido-3-oxo-1,2-benzothiazol-2(3H)-yl)aurate(1-)
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66% inhibition at 0.02 mM
RLLGAP-(cis-4-aminocyclohexane carboxylic acid)-QLVSGI-betaAla-betaAla-PW
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RLLGAPV-(cis-4-aminocyclohexane carboxylic acid)-RQLVSGI
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63% inhibition at 0.005 mM
RLLGAPV-(cis-4-aminocyclohexane carboxylic acid)-RQLVSGI-betaAla-betaAla-PW
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SERPINB3
potent cross-class inhibitor of cysteine cathepsins L, K, S and papain, inhibits proteolytic activities as well as specific hemoglobinolytic activity of FP2 via noncovalent interaction. Disease state mutant serpin-Gly351Ala displays better anti-protease activity against FP2
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[(3R)-2-oxo-1-(2-oxo-2-[[(2E)-4-oxopent-2-en-1-yl]amino]ethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]methyl [4-chloro-2-(trifluoromethyl)phenyl]carbamate
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[(5Z)-2,4-dioxo-5-(2,4,6-trimethoxybenzylidene)-1,3-thiazolidin-3-yl]acetic acid
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[3-benzyl-2-(pyridin-2-yl-kappaN)-4,5-dihydro-1,3-oxazol-3-ium-kappaN](dichloro)aurate(1-) hexafluorophosphate
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54% inhibition at 0.02 mM
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compound provides complete protection to the infected mice at 24 mg/kg for 4 days
3-(1-benzoyl-5-(4-flurophenyl)-4,5-dihydro-1H-pyrazol-3yl)-7-(diethyamino)-2H-chromen-2-one
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additional information
density functional theory calculations of binding of different derivatives of acetophenone thiosemicarbazone and propiophenone thiosemicarbazone acting as inhibitors reveal covalent interaction between the thiocarbonyl carbon of the thiosemicarbazone moiety and the thiolate sulfur of the active site cysteine residue of falcipain-2. Acetophenone thiosemicarbazone and propiophenone thiosemicarbazone derivatives are potential reversible covalent inhibitors of falcipain-2
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additional information
analysis of binding modes for 20 reversible peptide-based inhibitors and identification of near-native ligand conformations. The reversibility of the studied inhibitors, together with their predicted substrate-like orientation and the presence of a scissile peptide-bond at the P1 site, suggest a noncovalent substrate-like inhibition mechanism
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additional information
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analysis of binding modes for 20 reversible peptide-based inhibitors and identification of near-native ligand conformations. The reversibility of the studied inhibitors, together with their predicted substrate-like orientation and the presence of a scissile peptide-bond at the P1 site, suggest a noncovalent substrate-like inhibition mechanism
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