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name Structure Reference Source Properties Activities Metabolism

Pepstatin

AlkaPlorer ID: AK021612

Synonym: 'Ahpatinin C', 'Pepsin inhibitor S 735A', 'Procidin S 735A', 'NSC 272671', 'Pepstatin A', 'Pepstatin'

IUPAC Name: (3S,4S)-3-hydroxy-4-[[(2S)-2-[[(3S,4S)-3-hydroxy-6-methyl-4-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoyl]amino]-6-methylheptanoic acid

Structure

SMILES: CC(C)CC(O)=N[C@H](C(O)=N[C@H](C(O)=N[C@@H](CC(C)C)[C@@H](O)CC(O)=N[C@@H](C)C(O)=N[C@@H](CC(C)C)[C@@H](O)CC(=O)O)C(C)C)C(C)C

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InChI: InChI=1S/C34H63N5O9/c1-17(2)12-23(37-33(47)31(21(9)10)39-34(48)30(20(7)8)38-27(42)14-19(5)6)25(40)15-28(43)35-22(11)32(46)36-24(13-18(3)4)26(41)16-29(44)45/h17-26,30-31,40-41H,12-16H2,1-11H3,(H,35,43)(H,36,46)(H,37,47)(H,38,42)(H,39,48)(H,44,45)/t22-,23-,24-,25-,26-,30-,31-/m0/s1

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InChIKey: FAXGPCHRFPCXOO-LXTPJMTPSA-N

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Properties Information

Molecule Weight: 685.9040000000002

TPSA？: 240.71

MolLogP？: 5.668700000000005

Number of H-Donors: 8

Number of H-Acceptors: 8

RingCount: 0

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bos taurus Cathepsin D IC50 10.0 nM 10.1021/jm00172a005
Bos taurus Cathepsin D IC50 28.0 nM 10.1021/jm00149a001
Bos taurus Cathepsin D IC50 28.0 nM 10.1021/jm00160a048
Bos taurus Cathepsin D IC50 28.0 nM 10.1021/jm00160a049
Bos taurus Cathepsin D Ki 0.5 nM 10.1021/jm00162a015
Candida albicans Candida albicans Activity 0.0 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candida albicans Activity 3.8 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candida albicans Activity 5.0 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candida albicans Activity 9.4 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candida albicans Activity 19.8 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candida albicans Activity 28.0 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candida albicans Activity 30.0 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candida albicans Activity 32.4 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candida albicans Activity 37.2 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candida albicans Activity 51.0 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candida albicans Activity 52.0 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candida albicans Activity 56.8 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candida albicans Activity 58.4 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candida albicans Activity 100.0 10'3CFU/ml 10.1021/jm901734u
Candida albicans Candidapepsin-1 Activity nan None 10.1128/aac.01072-07
Candida albicans Candidapepsin-2 Activity nan None 10.1128/aac.01072-07
Candida albicans Candidapepsin-2 IC50 90.0 nM 10.1016/j.bmc.2012.09.031
Candida albicans Candidapepsin-3 Activity nan None 10.1128/aac.01072-07
Candida albicans Candidapepsin-6 Activity nan None 10.1128/aac.01072-07
Candida albicans Candidapepsin-8 Activity nan None 10.1128/aac.01072-07
Candida albicans Candidapepsin-9 Activity nan None 10.1128/aac.01072-07
Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) Candidapepsin-5 Activity nan None 10.1128/aac.01072-07
Candida albicans (strain WO-1) (Yeast) Candidapepsin-4 Activity nan None 10.1128/aac.01072-07
Chlorocebus sabaeus Vero C1008 AUC cytotoxicity 262.3 None 10.1038/s41586-020-2286-9
Chlorocebus sabaeus Vero C1008 pCC50 7.71 None 10.1038/s41586-020-2286-9
Hepatitis C virus genotype 1a (isolate H) (HCV) Genome polyprotein IC50 500.0 nM None
Homo sapiens ADAM9 IC50 56.3 nM 10.1021/jm9009394
Homo sapiens ATP-dependent DNA helicase Q1 Potency 31622.8 nM None
Homo sapiens Beta-secretase 1 Activity nan None 10.1016/j.bmcl.2003.11.061
Homo sapiens Cathepsin B IC50 4260.0 nM 10.1021/jm8014734
Homo sapiens Cathepsin D Activity 34.0 % 10.1021/acs.jnatprod.7b00551
Homo sapiens Cathepsin D Activity 36.0 % 10.1021/acs.jnatprod.7b00551
Homo sapiens Cathepsin D IC50 0.0016 ug.mL-1 10.1007/s00044-012-0397-z
Homo sapiens Cathepsin D IC50 0.05 nM 10.1021/acs.jnatprod.8b00417
Homo sapiens Cathepsin D IC50 0.1 nM 10.1021/acs.jnatprod.7b00551
Homo sapiens Cathepsin D IC50 0.173 nM 10.1021/jm9009394
Homo sapiens Cathepsin D IC50 0.35 nM 10.1016/j.bmc.2016.04.062
Homo sapiens Cathepsin D IC50 0.35 nM 10.1021/acs.jnatprod.7b00551
Homo sapiens Cathepsin D IC50 0.49 nM 10.1021/acs.jmedchem.9b01351
Homo sapiens Cathepsin D IC50 0.55 nM 10.1016/j.bmcl.2008.02.060
Homo sapiens Cathepsin D IC50 0.693 nM 10.1016/j.bmc.2022.116646
Homo sapiens Cathepsin D IC50 0.693 nM 10.1021/jm301630s
Homo sapiens Cathepsin D IC50 1.0 nM 10.1016/j.bmc.2020.115879
Homo sapiens Cathepsin D IC50 1.0 nM 10.1016/j.bmcl.2014.07.054
Homo sapiens Cathepsin D IC50 2.0 nM 10.1016/s0960-894x(99)00433-3
Homo sapiens Cathepsin D IC50 2.3 nM 10.1016/j.bmcl.2006.06.010
Homo sapiens Cathepsin D IC50 5.0 nM 10.1021/jm9009394
Homo sapiens Cathepsin D IC50 100.0 nM 10.1021/acs.jnatprod.7b00551
Homo sapiens Cathepsin D IC50 1000.0 nM 10.1021/acs.jnatprod.7b00551
Homo sapiens Cathepsin D IC50 5000.0 nM 10.1021/jm9009394
Homo sapiens Cathepsin D IC50 100000.0 nM 10.1021/jm8014734
Homo sapiens Cathepsin D INH 0.1 nM 10.1016/j.bmc.2022.117043
Homo sapiens Cathepsin D Inhibition 50.0 % 10.1021/acs.jnatprod.7b00551
Homo sapiens Cathepsin D Inhibition 98.7 % 10.1016/j.bmc.2020.115879
Homo sapiens Cathepsin D Inhibition 99.71 % 10.1016/j.ejmech.2022.114851
Homo sapiens Cathepsin D Inhibition nan % 10.1021/acs.jnatprod.7b00551
Homo sapiens Cathepsin D Ki 0.01 nM 10.1021/jm990412m
Homo sapiens Cathepsin D Log Kd -11.43 None 10.1021/jm0105833
Homo sapiens Cathepsin D Ratio IC50 20.0 None 10.1021/jm9009394
Homo sapiens Cathepsin D Ratio IC50 1000.0 None 10.1021/jm9009394
Homo sapiens Cathepsin D Ratio IC50 29000.0 None 10.1021/jm9009394
Homo sapiens Cathepsin E IC50 0.08 nM 10.1016/j.bmc.2016.04.062
Homo sapiens Cathepsin E IC50 0.1 nM 10.1021/acs.jnatprod.7b00551
Homo sapiens Cathepsin E IC50 0.181 nM 10.1021/jm9009394
Homo sapiens Cathepsin E IC50 0.3 nM 10.1021/acs.jnatprod.7b00551
Homo sapiens Cathepsin E IC50 0.446 nM 10.1016/j.bmc.2022.116646
Homo sapiens Cathepsin E IC50 0.446 nM 10.1021/jm301630s
Homo sapiens Cathepsin E IC50 5.0 nM 10.1021/jm9009394
Homo sapiens Cathepsin E IC50 7.5 nM 10.1016/j.bmcl.2014.07.054
Homo sapiens Cathepsin E IC50 100.0 nM 10.1021/acs.jnatprod.7b00551
Homo sapiens Cathepsin E IC50 1000.0 nM 10.1021/acs.jnatprod.7b00551
Homo sapiens Cathepsin E IC50 5000.0 nM 10.1021/jm9009394
Homo sapiens Cathepsin E Ratio IC50 20.0 None 10.1021/jm9009394
Homo sapiens Cathepsin E Ratio IC50 1000.0 None 10.1021/jm9009394
Homo sapiens Cathepsin E Ratio IC50 29000.0 None 10.1021/jm9009394
Homo sapiens Cathepsin H IC50 100000.0 nM 10.1021/jm8014734
Homo sapiens Cathepsin L IC50 800.0 nM 10.1021/jm8014734
Homo sapiens Cathepsin L Inhibition nan % 10.1016/j.ejmech.2022.114851
Homo sapiens Chymotrypsin C IC50 100000.0 nM 10.1021/jm00172a005
Homo sapiens Geminin Potency 517.4 nM None
Homo sapiens Histone acetyltransferase GCN5 Potency 17782.8 nM None
Homo sapiens Histone acetyltransferase GCN5 Potency 39810.7 nM None
Homo sapiens Histone deacetylase 6 Inhibition -5.61 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 0.56 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 251.2 nM None
Homo sapiens MDA-MB-231 Activity 48.0 % 10.1021/acs.jnatprod.7b00551
Homo sapiens MDA-MB-231 Activity nan None 10.1021/acs.jnatprod.7b00551
Homo sapiens MDA-MB-231 IC50 nan None 10.1007/s00044-012-0397-z
Homo sapiens NHDF Activity nan None 10.1021/acs.jmedchem.9b01351
Homo sapiens Parathyroid hormone receptor Potency 125892.5 nM None
Homo sapiens PBMC Activity nan None 10.1021/acs.jmedchem.9b01351
Homo sapiens Pepsin A IC50 59.0 nM 10.1021/jm980015w
Homo sapiens Regulator of G-protein signaling 4 Potency 5972.8 nM None
Homo sapiens Renin IC50 1300.0 nM 10.1021/jm00150a007
Homo sapiens Renin IC50 1400.0 nM 10.1021/jm00157a006
Homo sapiens Renin IC50 2000.0 nM 10.1021/jm00157a006
Homo sapiens Renin IC50 3200.0 nM 10.1021/jm00126a038
Homo sapiens Renin IC50 3200.0 nM 10.1021/jm00390a018
Homo sapiens Renin IC50 6000.0 nM 10.1021/jm00149a001
Homo sapiens Renin IC50 6000.0 nM 10.1021/jm00160a048
Homo sapiens Renin IC50 6000.0 nM 10.1021/jm00160a049
Homo sapiens Renin IC50 14000.0 nM 10.1021/jm00157a006
Homo sapiens Renin IC50 15000.0 nM 10.1021/jm00157a006
Homo sapiens Renin IC50 22000.0 nM 10.1021/jm00150a007
Homo sapiens Renin IC50 22000.0 nM 10.1021/jm00381a001
Homo sapiens Renin IC50 22000.0 nM 10.1021/jm00396a006
Homo sapiens Renin IC50 29300.0 nM 10.1021/jm00171a033
Homo sapiens Renin IC50 41000.0 nM 10.1021/jm00126a038
Homo sapiens Renin IC50 92000.0 nM 10.1021/jm00172a005
Homo sapiens Renin Ki 100.0 nM 10.1021/jm00136a001
Homo sapiens Renin Ki 13000.0 nM 10.1021/jm00150a007
Homo sapiens TAR DNA-binding protein 43 Potency 354.8 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 79432.8 nM None
Homo sapiens Vitamin D receptor Potency 89125.1 nM None
Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 51800.0 nM 10.1021/np0003995
Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 69000.0 nM 10.1021/np0003995
Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 150000.0 nM 10.1021/np0003995
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 protease Inhibition 23.0 % 10.1016/j.bmcl.2004.09.034
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 protease Ki 16.98 nM 10.1021/jm00038a006
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 protease Ki 230.0 nM 10.1021/jm5008352
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 protease Ki 1400.0 nM 10.1021/jm00112a001
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 protease Ki 3100.0 nM 10.1021/jm00041a005
Human immunodeficiency virus 1 Protease IC50 0.001 ug.mL-1 10.1021/np8001139
Human immunodeficiency virus 1 Protease IC50 41.0 nM 10.1016/j.bmc.2009.03.059
Human immunodeficiency virus 1 Protease IC50 1300.0 nM 10.1016/j.bmc.2009.03.019
Human immunodeficiency virus 1 Protease IC50 1500.0 nM 10.1021/jm701575k
Human immunodeficiency virus 1 Protease Inhibition 56.0 % 10.1016/j.ejmech.2014.07.049
Human immunodeficiency virus 1 Protease Inhibition 74.0 % 10.1016/j.ejmech.2014.07.049
Human immunodeficiency virus 1 Protease Inhibition nan % 10.1016/j.ejmech.2015.06.054
Human immunodeficiency virus 1 Protease Ki 36.0 nM 10.1016/j.bmc.2013.06.018
Human immunodeficiency virus 1 Protease Ki 38.0 nM 10.1016/j.bmc.2009.03.059
Human immunodeficiency virus 1 Protease Ki 50.0 nM 10.1016/j.bmc.2009.03.059
Human immunodeficiency virus 1 Protease Ki 51.0 nM 10.1016/j.bmc.2013.06.018
Human immunodeficiency virus 1 Protease Ki 52.0 nM 10.1016/j.bmc.2013.06.018
Human immunodeficiency virus 1 Protease Ki 94.0 nM 10.1021/jm5008352
Human immunodeficiency virus 1 Protease Ki 1100.0 nM 10.1021/np0003995
Human T-cell leukemia virus 1 (strain Japan ATK-1 subtype A) (HTLV-1) Human T-cell leukemia virus type I protease Inhibition 15.0 % 10.1016/j.bmcl.2004.09.034
Human T-cell leukemia virus 1 (strain Japan ATK-1 subtype A) (HTLV-1) Human T-cell leukemia virus type I protease Inhibition 17.0 % 10.1016/j.bmcl.2004.09.034
Human T-cell leukemia virus 1 (strain Japan ATK-1 subtype A) (HTLV-1) Human T-cell leukemia virus type I protease Ki 14600.0 nM 10.1016/j.bmcl.2004.09.034
Human T-cell leukemia virus 1 (strain Japan ATK-1 subtype A) (HTLV-1) Human T-cell leukemia virus type I protease Ki 36500.0 nM 10.1016/j.bmcl.2004.09.034
Leishmania donovani Cysteine protease IC50 160.0 nM 10.1021/jm0493717
Mus musculus Mus musculus Inhibition 91.91 % 10.1021/jm058208o
Oryctolagus cuniculus Angiotensin-converting enzyme IC50 100000.0 nM 10.1021/jm00172a005
Plasmodium berghei Plasmodium berghei Inhibition 92.94 % 10.1016/j.bmc.2008.02.011
Plasmodium berghei Plasmodium berghei Inhibition 92.94 % 10.1016/j.ejmech.2008.08.005
Plasmodium berghei Plasmodium berghei Inhibition 95.45 % 10.1016/j.bmc.2011.01.050
Plasmodium falciparum Plasmepsin 1 IC50 0.9 nM 10.1016/j.bmc.2018.04.012
Plasmodium falciparum Plasmepsin 2 Activity 85.2 % 10.1021/jm100233b
Plasmodium falciparum Plasmepsin 2 IC50 0.42 nM 10.1016/j.bmc.2018.04.012
Plasmodium falciparum Plasmepsin 2 IC50 0.68 nM 10.1016/j.bmcl.2008.02.060
Plasmodium falciparum Plasmepsin 2 Inhibition 82.8 % 10.1021/jm100233b
Plasmodium falciparum Plasmepsin 2 Inhibition 97.8 % 10.1021/jm100233b
Plasmodium falciparum Plasmepsin 4 IC50 0.3 nM 10.1016/j.bmc.2018.04.012
Plasmodium falciparum Plasmodium falciparum Activity 93.77 % 10.1016/j.ejmech.2008.09.044
Plasmodium falciparum Plasmodium falciparum Activity nan None 10.1128/aac.00840-06
Plasmodium falciparum Plasmodium falciparum EC50 14000.0 nM 10.1128/aac.00840-06
Plasmodium falciparum Plasmodium falciparum EC50 nan None 10.1128/aac.00840-06
Plasmodium falciparum Plasmodium falciparum IC50 29360.0 nM 10.1128/aac.00057-08
Plasmodium falciparum Plasmodium falciparum IC50 39200.0 nM 10.1128/aac.00057-08
Plasmodium falciparum Plasmodium falciparum Potency 5858.4 nM None
Plasmodium falciparum Plasmodium falciparum Potency 9285.0 nM None
Rattus norvegicus Renin IC50 1000.0 nM 10.1021/jm00157a006
Rattus norvegicus Renin IC50 8300.0 nM 10.1021/jm00157a006
Rattus norvegicus Renin IC50 13000.0 nM 10.1021/jm00396a006
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 9.112 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 13.53 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 AUC 313.0 None 10.1038/s41586-020-2286-9
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 776.25 nM 10.1038/s41586-020-2286-9
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.04 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.02 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 49.0 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition index -0.009251 None 10.1101/2020.04.03.023846
Sus scrofa Pepsin A IC50 7.0 nM 10.1021/jm00111a054
Sus scrofa Pepsin A IC50 10.0 nM 10.1021/jm00149a001
Sus scrofa Pepsin A IC50 10.0 nM 10.1021/jm00160a048
Sus scrofa Pepsin A IC50 10.0 nM 10.1021/jm00160a049
Sus scrofa Pepsin A IC50 18.0 nM 10.1021/jm00172a005
Sus scrofa Pepsin A Ki 4.6e-08 nM 10.1021/jm00111a054
Sus scrofa Pepsin A Ki 0.056 nM 10.1021/jm00381a001
Trypanosoma brucei 6-phospho-1-fructokinase Potency 5358.2 nM None
Trypanosoma cruzi Cruzipain Potency 31622.8 nM None
None ADMET AUC Ratio 0.838 None 10.1038/s41586-020-2286-9
None ADMET Inhibition 91.91 % 10.1016/j.ejmech.2007.01.001
None ADMET Papp 1.1 10'-7 cm/s 10.1021/acs.jmedchem.9b01351
None ADMET TI 1.4 None 10.1021/np0003995
None No relevant target Solubility 197.0 ug.mL-1 10.1021/acs.jmedchem.9b01351
None Unchecked Activity nan None 10.1074/jbc.m703643200
None Unchecked IC50 0.0015 ug.mL-1 10.1021/np0200616
None Unchecked IC50 0.006 ug.mL-1 10.1021/np010042g
None Unchecked IC50 0.006 ug.mL-1 10.1021/np0200717
None Unchecked IC50 0.1 nM 10.1016/j.bmcl.2014.07.054
None Unchecked IC50 3.0 nM 10.1021/np8002707
None Unchecked IC50 16.0 nM 10.1021/np010172p
None Unchecked IC50 22.0 nM 10.1016/j.ejmech.2020.112515
None Unchecked IC50 31.0 nM 10.1021/jm9807306
None Unchecked IC50 310.0 nM 10.1021/np010172p
None Unchecked IC50 nan None 10.1016/j.bmc.2009.03.019
None Unchecked ID50 0.0052 ug ml-1 10.1021/jm00191a023
None Unchecked ID50 2.0 ug ml-1 10.1021/jm00191a023
None Unchecked Inhibition 100.0 % 10.1016/j.ejmech.2020.112515
None Unchecked Ki 0.15 nM 10.1021/jm00381a001
None Unchecked Potency 22387.2 nM None
None Unchecked Ratio IC50 1.1 None 10.1021/acs.jnatprod.7b00551
None Unchecked Ratio IC50 4.4 None 10.1016/j.bmc.2016.04.062
None Unchecked Ratio Ki 2.5 None 10.1021/jm5008352

Metabolism Information