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Compound Detail

CHEMBL4763675

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CN[C@@H]1C[C@H]2O[C@@](C)([C@@H]1OC)n1c3ccccc3c3c4c(c5c6ccccc6n2c5c31)C(=O)NC4=O

Basic Information

ChEMBL ID CHEMBL4763675
Phase Preclinical
Structure Type MOL
InChI Key POTTVLREWUNNRO-UGZRAAABSA-N
13
Targets
16
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

480.5
MW (Da)
3.99
ALogP
7
HBA
2
HBD
86.5
PSA (Ų)
0.37
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C28H24N4O4
MW 480.52
Aromatic Rings 5
Heavy Atoms 36
NP-Likeness 1.08

Activity Summary

IC50 16 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Leishmania amazonensis
CHEMBL612877
IC50 9.7 8.925 0.2 2
Leishmania donovani
CHEMBL367
IC50 9.0 9.0 1.0 1
Protein kinase C theta type
CHEMBL3920
IC50 8.22 7.995 6.0 2
Rho-associated protein kinase 2
CHEMBL2973
IC50 7.7 7.105 20.0 2
Protein kinase C delta type
CHEMBL2996
IC50 7.68 7.68 21.0 1
BXPC-3
CHEMBL614530
IC50 6.37 6.37 430.0 1
A549
CHEMBL392
IC50 6.11 6.11 780.0 1
ASPC1
CHEMBL612588
IC50 5.92 5.92 1200.0 1
RKO
CHEMBL614879
IC50 5.83 5.83 1470.0 1
MGC-803
CHEMBL3706566
IC50 5.82 5.82 1520.0 1
PC-9
CHEMBL614102
IC50 5.73 5.73 1880.0 1
NCI-H1975
CHEMBL614348
IC50 5.7 5.7 2010.0 1
NCI-H1299
CHEMBL612255
IC50 5.69 5.69 2030.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Leishmania amazonensis IC50 = 0.2 nM 9.7 Antileishmanial activity against Leishmania amazonensis amastigotes assessed as ... 37421889
Leishmania donovani IC50 = 1.0 nM 9.0 Antileishmanial activity against Leishmania donovani promastigotes assessed as r... 37421889
Protein kinase C theta type IC50 = 6.0 nM 8.22 Inhibition of PKCtheta (unknown origin) by HTRF assay 33100009
Leishmania amazonensis IC50 = 7.0 nM 8.15 Antileishmanial activity against Leishmania amazonensis MHOM/BR/77/LTB001 assess... 37421889
Protein kinase C theta type IC50 = 17.0 nM 7.77 Inhibition of PKCtheta (unknown origin) by HTRF assay 33100009
Rho-associated protein kinase 2 IC50 = 20.0 nM 7.7 Inhibition of N-terminal His10-StrepII tagged human ROCK2 catalytic domain (1 to... 36764122
Protein kinase C delta type IC50 = 21.0 nM 7.68 Inhibition of PKCdelta (unknown origin) by HTRF assay 33100009
Rho-associated protein kinase 2 IC50 = 310.0 nM 6.51 Inhibition of N-terminal His10-StrepII tagged human ROCK2 catalytic domain (1 to... 36764122
BXPC-3 IC50 = 430.0 nM 6.37 Cytotoxicity in human BXPC-3 cells assessed as reduction in cell viability incub... 33100009
A549 IC50 = 780.0 nM 6.11 Cytotoxicity in human A549 cells assessed as reduction in cell viability incubat... 33100009
ASPC1 IC50 = 1200.0 nM 5.92 Cytotoxicity in human ASPC1 cells assessed as reduction in cell viability incuba... 33100009
RKO IC50 = 1470.0 nM 5.83 Cytotoxicity in human RKO cells assessed as reduction in cell viability incubate... 33100009
MGC-803 IC50 = 1520.0 nM 5.82 Cytotoxicity in human MGC-803 cells assessed as reduction in cell viability incu... 33100009
PC-9 IC50 = 1880.0 nM 5.73 Cytotoxicity in human PC-9 cells assessed as reduction in cell viability incubat... 33100009
NCI-H1975 IC50 = 2010.0 nM 5.7 Cytotoxicity in human NCI-H1975 cells assessed as reduction in cell viability in... 33100009
NCI-H1299 IC50 = 2030.0 nM 5.69 Cytotoxicity in human NCI-H1299 cells assessed as reduction in cell viability in... 33100009

Literature References

PubMed DOI Target Context # Activities
33100009 10.1021/acs.jmedchem.0c01271 BXPC-3 15
33100009 10.1021/acs.jmedchem.0c01271 Unchecked 15
33100009 10.1021/acs.jmedchem.0c01271 ADMET 6
33100009 10.1021/acs.jmedchem.0c01271 Protein kinase C theta type 5
36764122 10.1016/j.ejmech.2023.115181 Rho-associated protein kinase 2 2
33100009 10.1021/acs.jmedchem.0c01271 Protein kinase C beta type 2
37421889 10.1016/j.ejmech.2023.115609 Leishmania amazonensis 2
33100009 10.1021/acs.jmedchem.0c01271 Protein kinase C delta type 2
33100009 10.1021/acs.jmedchem.0c01271 NCI-H1975 1
33100009 10.1021/acs.jmedchem.0c01271 PC-9 1
33100009 10.1021/acs.jmedchem.0c01271 RKO 1
33100009 10.1021/acs.jmedchem.0c01271 MGC-803 1
33100009 10.1021/acs.jmedchem.0c01271 NCI-H1299 1
33100009 10.1021/acs.jmedchem.0c01271 Transcription factor p65 1
33100009 10.1021/acs.jmedchem.0c01271 NF-kappa-B inhibitor alpha 1
33100009 10.1021/acs.jmedchem.0c01271 Inhibitor of nuclear factor kappa-B kinase subunit alpha 1
37421889 10.1016/j.ejmech.2023.115609 Leishmania donovani 1
33100009 10.1021/acs.jmedchem.0c01271 PKC alpha and beta-2 1
33100009 10.1021/acs.jmedchem.0c01271 Protein kinase C alpha type 1
33100009 10.1021/acs.jmedchem.0c01271 A549 1

Data from ChEMBL 36 via Core Engine