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Compound Detail

CHEMBL296588

PEPSTATIN
🧪 Phase II
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🧪 Phase II
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
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL296588
Name PEPSTATIN
Phase Phase II
Structure Type MOL
InChI Key FAXGPCHRFPCXOO-LXTPJMTPSA-N

Known Names

NSC-272671 Pepstatin Pepstatin a Pepstatina Pepstatine
22
Targets
103
Activities
3
Assay Types
1
PK Parameters
20
Publications
5
Known Names

Molecular Properties

685.9
MW (Da)
1.47
ALogP
8
HBA
8
HBD
223.3
PSA (Ų)
0.08
QED
2
Ro5 Violations
22
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -stat-
USAN Year 1972

Extended Properties

Molecular Formula C34H63N5O9
MW 685.90
Aromatic Rings 0
Heavy Atoms 48
NP-Likeness 0.29

Activity Summary

IC50 78 meas. best 10.3
Ki 21 meas. best 11.0
EC50 4 meas. best 4.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cathepsin D
CHEMBL2581
 Ki 11.0 11.0 0.0 1
Cathepsin D
CHEMBL2581
 IC50 10.3 8.654 0.1 15
Pepsin A
CHEMBL2714
 Ki 10.25 10.25 0.1 1
Cathepsin E
CHEMBL3092
 IC50 10.1 8.466 0.1 10
Unchecked
CHEMBL612545
 IC50 10.0 7.9 0.1 7
Unchecked
CHEMBL612545
 Ki 9.82 9.82 0.1 1
Plasmepsin 4
CHEMBL3988607
 IC50 9.52 9.52 0.3 1
Plasmepsin II
CHEMBL4414
 IC50 9.38 9.275 0.4 2
Cathepsin D
CHEMBL4106
 Ki 9.3 9.3 0.5 1
Plasmepsin I
CHEMBL4687
 IC50 9.05 9.05 0.9 1
Pepsin A
CHEMBL2714
 IC50 8.15 7.98 7.0 5
Cathepsin D
CHEMBL4106
 IC50 8.0 7.6625 10.0 4
Human immunodeficiency virus type 1 protease
CHEMBL243
 Ki 7.77 6.4425 17.0 4
Protease
CHEMBL2366517
 Ki 7.44 7.1425 36.0 8
Protease
CHEMBL2366517
 IC50 7.39 6.3667 41.0 3
Disintegrin and metalloproteinase domain-containing protein 9
CHEMBL5982
 IC50 7.25 7.25 56.3 1
Pepsin A
CHEMBL3295
 IC50 7.23 7.23 59.0 1
Secreted aspartic protease 2
CHEMBL6021
 IC50 7.05 7.05 90.0 1
Renin
CHEMBL286
 Ki 7.0 5.945 100.0 2
Cysteine protease
CHEMBL4751
 IC50 6.8 6.8 160.0 1
Genome polyprotein
CHEMBL3638344
 IC50 6.3 6.3 500.0 1
Procathepsin L
CHEMBL3837
 IC50 6.1 6.1 800.0 1
Renin
CHEMBL2322
 IC50 6.0 5.3233 1000.0 3
Renin
CHEMBL286
 IC50 5.89 5.0444 1300.0 16
Cathepsin B
CHEMBL4072
 IC50 5.37 5.37 4260.0 1
Plasmodium falciparum
CHEMBL364
 EC50 4.85 4.85 14000.0 1
Gag-Pro polyprotein
CHEMBL3346
 Ki 4.84 4.64 14600.0 2
Plasmodium falciparum
CHEMBL364
 IC50 4.53 4.47 29360.0 2
Human immunodeficiency virus 1
CHEMBL378
 EC50 4.29 4.225 51800.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 313.0 - Chlorocebus sabaeus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cathepsin D Ki = 0.01 nM 11.0 Binding affinity against human cathepsin D 10669559
Cathepsin D IC50 = 0.05 nM 10.3 Inhibition of human cathepsin D using GKPILFFRLK(DNP)-D-RNH2) labeled MCA as sub... 29944370
Pepsin A Ki = 0.056 nM 10.25 Inhibition of porcine pepsin 3882966
Cathepsin E IC50 = 0.08 nM 10.1 Inhibition of human recombinant cathepsin E using Mca-Gly-Lys-Pro-Ile-Leu-Phe-Ph... 27211244
Unchecked IC50 = 0.1 nM 10.0 Inhibition of pepsin (unknown origin) 25086681
Cathepsin D IC50 = 0.1 nM 10.0 Inhibition of secreted cathepsin D in human MDA-MB-231 cells using Mca-Gly-Lys-P... 29087712
Cathepsin E IC50 = 0.1 nM 10.0 Inhibition of secreted cathepsin E in human MDA-MB-231 cells using Mca-Gly-Lys-P... 29087712
Unchecked Ki = 0.15 nM 9.82 Compound was evaluated for the ability to inhibit penicillopepsin. 3882966
Cathepsin D IC50 = 0.173 nM 9.76 Inhibition of cathepsin D 19715320
Cathepsin E IC50 = 0.181 nM 9.74 Inhibition of cathepsin E 19715320
Cathepsin E IC50 = 0.3 nM 9.52 Inhibition of recombinant human C-terminal His10-tagged cathepsin E (Gln18 to Pr... 29087712
Plasmepsin 4 IC50 = 0.3 nM 9.52 Inhibition of Plasmodium falciparum plasmepsin 4 using DABCYL-Glu-Arg-Nle-Phe-Le... 29636223
Cathepsin D IC50 = 0.35 nM 9.46 Inhibition of human liver cathepsin D using Mca-Gly-Lys-Pro-Ile-Leu-Phe-Phe-Arg-... 27211244
Cathepsin D IC50 = 0.35 nM 9.46 Inhibition of human liver cathepsin D using Mca-Gly-Lys-Pro-Ile-Leu-PhePhe-Arg-L... 29087712
Plasmepsin II IC50 = 0.42 nM 9.38 Inhibition of Plasmodium falciparum plasmepsin-2 using DABCYL-Glu-Arg-Nle-Phe-Le... 29636223
Cathepsin E IC50 = 0.446 nM 9.35 Inhibition of cathepsin E by fluorescence assay 23181502
Cathepsin E IC50 = 0.446 nM 9.35 Inhibition of Cathepsin E (unknown origin) using Mca-Gly-Lys-Pro-Ile-Leu-Phe-Phe... 35121401
Cathepsin D IC50 = 0.49 nM 9.31 Inhibition of human placenta CatD using Abz-Lys-Pro-Ala-Glu-Phe-Nph-Ala-Leu as s... 32003991
Cathepsin D Ki = 0.5 nM 9.3 Inhibition of cathepsin D. 3783611
Cathepsin D IC50 = 0.55 nM 9.26 Inhibition of human cathepsin D by FRET assay 18417344

Literature References

PubMed DOI Target Context # Activities
20184325 10.1021/jm901734u Candida albicans 16
29087712 10.1021/acs.jnatprod.7b00551 Cathepsin D 11
19715320 10.1021/jm9009394 Cathepsin E 6
3543358 10.1021/jm00157a006 Renin 6
19715320 10.1021/jm9009394 Cathepsin D 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
19394228 10.1016/j.bmc.2009.03.059 Protease 4
15501070 10.1016/j.bmcl.2004.09.034 Gag-Pro polyprotein 4
29087712 10.1021/acs.jnatprod.7b00551 Cathepsin E 4
23911197 10.1016/j.bmc.2013.06.018 Protease 3
3906131 10.1021/jm00150a007 Renin 3
11430019 10.1021/np0003995 Human immunodeficiency virus 1 3
20438064 10.1021/jm100233b Plasmepsin II 3
17088482 10.1128/aac.00840-06 Plasmodium falciparum 3
25042102 10.1016/j.ejmech.2014.07.049 Protease 2
18443109 10.1128/aac.00057-08 Plasmodium falciparum 2
3275777 10.1021/jm00396a006 Renin 2
379333 10.1021/jm00191a023 Unchecked 2
17954688 10.1128/aac.01072-07 Secreted aspartic protease 2 2
2067002 10.1021/jm00111a054 Pepsin A 2

Data from ChEMBL 36 via Core Engine