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Literature summary extracted from

  • Ersmark, K.; Feierberg, I.; Bjelic, S.; Hamelink, E.; Hackett, F.; Blackman, M.J.; Hulten, J.; Samuelsson, B.; Aqvist, J.; Hallberg, A.
    Potent inhibitors of the Plasmodium falciparum enzymes plasmepsin I and II devoid of cathepsin D inhibitory activity (2004), J. Med. Chem., 47, 110-122.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(2,4-dimethoxy-3,5-pyrimidin)-2-propenyl-oxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(2,5-dimethyl-3,4-oxazol)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(3,4-methylenedioxyphenyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(3-thienyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(4-acetylphenyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(4-fluorophenyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(4-tolyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-bromo-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-phenyl-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-5-phenyl-pent-2-en-4-ynyl]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-5-trimethylsilyl-pent-2-en-4-ynyl]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-pent-2-en-4-ynyl]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E,4E)-5-(methoxycarbonyl)-pent-2,4-dienyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E,4E)-5-phenyl-pentadienyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 2,5-Bis-allyloxy-3,4-dihydroxy-hexanedioic acid bis-[(2-hydroxy-indan-1-yl)-amide]
-
 Plasmodium falciparum
3.4.23.38 2,5-Bis-benzyloxy-3,4-dihydroxy-hexanedioic acid bis-[(2-hydroxy-indan-1-yl)-amide]
-
 Plasmodium falciparum
3.4.23.38 N-[1-Benzyl-3-(2-biphenyl-4-yl-1-carbamoyl-ethylamino)-2-hydroxy-propyl]-2-(3-1H-indol-3-yl-propionylamino)-3-methyl-butyramide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(2,4-dimethoxy-3,5-pyrimidin)-2-propenyl-oxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(2,5-dimethyl-3,4-oxazol)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(3,4-methylenedioxyphenyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(3-thienyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(4-acetylphenyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(4-fluorophenyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(4-tolyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-bromo-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-phenyl-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-5-phenyl-pent-2-en-4-ynyl]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-5-trimethylsilyl-pent-2-en-4-ynyl]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-pent-2-en-4-ynyl]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E,4E)-5-(methoxycarbonyl)-pent-2,4-dienyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E,4E)-5-phenyl-pentadienyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 2,5-Bis-allyloxy-3,4-dihydroxy-hexanedioic acid bis-[(2-hydroxy-indan-1-yl)-amide]
-
 Plasmodium falciparum
3.4.23.39 2,5-Bis-benzyloxy-3,4-dihydroxy-hexanedioic acid bis-[(2-hydroxy-indan-1-yl)-amide]
-
 Plasmodium falciparum
3.4.23.39 N-[1-Benzyl-3-(2-biphenyl-4-yl-1-carbamoyl-ethylamino)-2-hydroxy-propyl]-2-(3-1H-indol-3-yl-propionylamino)-3-methyl-butyramide
-
 Plasmodium falciparum

Organism

EC Number Organism UniProt Comment Textmining
3.4.23.38 Plasmodium falciparum
-
-
-
3.4.23.39 Plasmodium falciparum
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
3.4.23.39
-
 Plasmodium falciparum

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.4.23.38 4-[[4'-(dimethylamino)phenyl]azo]-benzoyl-Glu-Arg-Nle-Phe-Leu-Ser-Phe-Pro-5-[(2'-aminoethyl)-amino]naphthalenesulfonic acid + H2O
-
 Plasmodium falciparum 4-[[4'-(dimethylamino)phenyl]azo]-benzoyl-Glu-Arg-Nle-Phe + Leu-Ser-Phe-Pro-5-[(2'-aminoethyl)-amino]naphthalenesulfonic acid
-
 ?
3.4.23.39 4-[[4'-(dimethylamino)phenyl]azo]-benzoyl-Glu-Arg-Nle-Phe-Leu-Ser-Phe-Pro-5-[(2'-aminoethyl)-amino]naphthalenesulfonic acid + H2O
-
 Plasmodium falciparum ?
-
 ?

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
3.4.23.38 0.0000005
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(3,4-methylenedioxyphenyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 0.0000008
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(4-acetylphenyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide the best dual inhibitor for EC 3.4.23.38 and EC 3.4.23.39 Plasmodium falciparum
3.4.23.38 0.0000013
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(3-thienyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 0.0000014
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-phenyl-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 0.0000026
-
 N-[1-Benzyl-3-(2-biphenyl-4-yl-1-carbamoyl-ethylamino)-2-hydroxy-propyl]-2-(3-1H-indol-3-yl-propionylamino)-3-methyl-butyramide
-
 Plasmodium falciparum
3.4.23.38 0.0000037
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E,4E)-5-(methoxycarbonyl)-pent-2,4-dienyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 0.0000044
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E,4E)-5-phenyl-pentadienyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 0.0000058
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(4-tolyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 0.0000072
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-5-phenyl-pent-2-en-4-ynyl]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 0.0000084
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(2,4-dimethoxy-3,5-pyrimidin)-2-propenyl-oxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 0.000023
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(2,5-dimethyl-3,4-oxazol)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 0.000025
-
 2,5-Bis-benzyloxy-3,4-dihydroxy-hexanedioic acid bis-[(2-hydroxy-indan-1-yl)-amide]
-
 Plasmodium falciparum
3.4.23.38 0.000027
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-bromo-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 0.000037
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-5-trimethylsilyl-pent-2-en-4-ynyl]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.38 0.000163
-
 2,5-Bis-allyloxy-3,4-dihydroxy-hexanedioic acid bis-[(2-hydroxy-indan-1-yl)-amide]
-
 Plasmodium falciparum
3.4.23.39 0.000006
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(4-acetylphenyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide the best dual inhibitor for EC 3.4.23.38 and EC 3.4.23.39 Plasmodium falciparum
3.4.23.39 0.0000089
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E,4E)-5-(methoxycarbonyl)-pent-2,4-dienyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 0.000011
-
 N-[1-Benzyl-3-(2-biphenyl-4-yl-1-carbamoyl-ethylamino)-2-hydroxy-propyl]-2-(3-1H-indol-3-yl-propionylamino)-3-methyl-butyramide
-
 Plasmodium falciparum
3.4.23.39 0.000013
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(2,4-dimethoxy-3,5-pyrimidin)-2-propenyl-oxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 0.000014
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(3,4-methylenedioxyphenyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 0.000015
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(3-thienyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 0.000015
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E,4E)-5-phenyl-pentadienyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 0.000029
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-phenyl-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 0.000032
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-pent-2-en-4-ynyl]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 0.000041
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-5-phenyl-pent-2-en-4-ynyl]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 0.000047
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-bromo-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 0.000059
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(4-fluorophenyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 0.000085
-
 2,5-Bis-benzyloxy-3,4-dihydroxy-hexanedioic acid bis-[(2-hydroxy-indan-1-yl)-amide]
-
 Plasmodium falciparum
3.4.23.39 0.000096
-
 2,5-Bis-allyloxy-3,4-dihydroxy-hexanedioic acid bis-[(2-hydroxy-indan-1-yl)-amide]
-
 Plasmodium falciparum
3.4.23.39 0.000129
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(4-tolyl)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum
3.4.23.39 0.000181
-
 (2R,3R,4R,5R)-N1,N6-bis[(1S,2R)-2-hydroxy-1-indanyl]-2,5-bis[(2E)-3-(2,5-dimethyl-3,4-oxazol)-2-propenyloxy]-3,4-dihydroxyhexane-1,6-diamide
-
 Plasmodium falciparum