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Compound Detail

CHEMBL2103847

TOSEDOSTAT
🧪 Phase II
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🧪 Phase II
CC(C)C[C@@H](C(=O)N[C@H](C(=O)OC1CCCC1)c1ccccc1)[C@H](O)C(=O)NO

Basic Information

ChEMBL ID CHEMBL2103847
Name TOSEDOSTAT
Phase Phase II
Structure Type MOL
InChI Key FWFGIHPGRQZWIW-SQNIBIBYSA-N

Known Names

CHR 2797 CHR-2797 CHR2797 Tosedostat
11
Targets
15
Activities
3
Assay Types
0
PK Parameters
20
Publications
4
Known Names
5
Indications
1
Mechanisms

Molecular Properties

406.5
MW (Da)
1.86
ALogP
6
HBA
4
HBD
125.0
PSA (Ų)
0.28
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -stat
USAN Year 2009

Extended Properties

Molecular Formula C21H30N2O6
MW 406.48
Aromatic Rings 1
Heavy Atoms 29
NP-Likeness 0.11

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Aminopeptidase inhibitor INHIBITOR Aminopeptidase

Indications

Leukemia, Myeloid, Acute Myelodysplastic Syndromes Carcinoma, Non-Small-Cell Lung Neoplasms Pancreatic Neoplasms

Activity Summary

IC50 11 meas. best 8.3
EC50 2 meas. best 5.68
Ki 2 meas. best 5.93

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytosol aminopeptidase
CHEMBL3965
IC50 8.3 8.3 5.0 1
Leukotriene A-4 hydrolase
CHEMBL4618
IC50 8.1 8.1 8.0 1
Aminopeptidase N
CHEMBL1907
IC50 7.52 6.62 30.0 3
72 kDa type IV collagenase
CHEMBL333
IC50 6.72 6.72 190.0 1
Puromycin-sensitive aminopeptidase
CHEMBL2264
IC50 6.58 6.58 260.0 2
Endoplasmic reticulum aminopeptidase 2
CHEMBL5043
IC50 6.11 6.11 770.0 1
Aminopeptidase N
CHEMBL1907
Ki 5.93 5.93 1180.0 1
Matrix metalloproteinase-9
CHEMBL321
IC50 5.82 5.82 1500.0 1
MOLT-4
CHEMBL614177
EC50 5.68 5.68 2100.0 1
HL-60
CHEMBL383
EC50 5.33 5.33 4700.0 1
Unchecked
CHEMBL612545
Ki 5.21 5.21 6150.0 1
Endoplasmic reticulum aminopeptidase 1
CHEMBL5939
IC50 4.75 4.75 18000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytosol aminopeptidase IC50 = 5.0 nM 8.3 Inhibition of human recombinant Leucine aminopeptidase 3 39011823
Leukotriene A-4 hydrolase IC50 = 8.0 nM 8.1 Inhibition of full length human recombinant Leukotriene A-4 hydrolase expressed ... 39011823
Aminopeptidase N IC50 = 30.0 nM 7.52 Inhibition of FLAG-tagged human recombinant Aminopeptidase N 39011823
72 kDa type IV collagenase IC50 = 190.0 nM 6.72 Inhibition of MMP2 (unknown origin) using QF-24 as substrate preincubated for 1 ... 31251594
Puromycin-sensitive aminopeptidase IC50 = 260.0 nM 6.58 Inhibition of recombinant human N-terminal His6-MBP-tagged PSA expressed in Esch... 28803047
Puromycin-sensitive aminopeptidase IC50 = 260.0 nM 6.58 Inhibition of human N-terminal His-tagged Puromycin-sensitive aminopeptidase ext... 38917665
Aminopeptidase N IC50 = 680.0 nM 6.17 Inhibition of recombinant human C-terminal His10-tagged APN (Lys69 to Lys967 res... 28803047
Aminopeptidase N IC50 = 680.0 nM 6.17 Inhibition of Aminopeptidase N (unknown origin) using Ala-AMC as substrate incub... 38917665
Endoplasmic reticulum aminopeptidase 2 IC50 = 770.0 nM 6.11 Inhibition of C-terminal Hexa-histidine-tagged human recombinant ERAP2 expressed... 39011823
Aminopeptidase N Ki = 1180.0 nM 5.93 Inhibition of soluble human APN ectodomain stably expressed in HEK293 GnTI(-) ce... 31251594
Matrix metalloproteinase-9 IC50 = 1500.0 nM 5.82 Inhibition of MMP9 (unknown origin) using QF-24 as substrate preincubated for 1 ... 31251594
MOLT-4 EC50 = 2100.0 nM 5.68 Antiproliferative activity against human MOLT4 cells after 72 hrs by MTT assay 28803047
HL-60 EC50 = 4700.0 nM 5.33 Antiproliferative activity against human HL60 cells after 72 hrs by MTT assay 28803047
Unchecked Ki = 6150.0 nM 5.21 Inhibition of Plasmodium falciparum M1 aminopeptidase 31251594
Endoplasmic reticulum aminopeptidase 1 IC50 = 18000.0 nM 4.75 Inhibition of C-terminal Hexa-histidine-tagged human recombinant ERAP1 expressed... 39011823

Literature References

PubMed DOI Target Context # Activities
28803047 10.1016/j.ejmech.2017.07.048 Aminopeptidase N 2
38917665 10.1016/j.ejmech.2024.116604 Aminopeptidase N 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
31251594 10.1021/acs.jmedchem.9b00757 Unchecked 1
28803047 10.1016/j.ejmech.2017.07.048 Puromycin-sensitive aminopeptidase 1
38917665 10.1016/j.ejmech.2024.116604 ADMET 1
39011823 10.1021/acs.jmedchem.4c00840 Endoplasmic reticulum aminopeptidase 2 1
39011823 10.1021/acs.jmedchem.4c00840 Endoplasmic reticulum aminopeptidase 1 1
28803047 10.1016/j.ejmech.2017.07.048 HeLa 1
28803047 10.1016/j.ejmech.2017.07.048 Vero 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
31251594 10.1021/acs.jmedchem.9b00757 Aminopeptidase N 1
28803047 10.1016/j.ejmech.2017.07.048 HL-60 1
31251594 10.1021/acs.jmedchem.9b00757 72 kDa type IV collagenase 1
31251594 10.1021/acs.jmedchem.9b00757 Matrix metalloproteinase-9 1
31251594 10.1021/acs.jmedchem.9b00757 Neutrophil collagenase 1
31251594 10.1021/acs.jmedchem.9b00757 Collagenase 3 1
31251594 10.1021/acs.jmedchem.9b00757 Matrilysin 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1

Data from ChEMBL 36 via Core Engine