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Compound Detail

CHEMBL116437

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CC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@@H](C=C(CO)C[C@]3(O)C(=O)C(C)=C[C@@H]23)[C@@H]2C(C)(C)[C@]12OC(C)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL116437
Phase Preclinical
Structure Type MOL
InChI Key OMHXSAMFEJVCPT-XQOWHXTBSA-N
6
Targets
14
Activities
3
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

448.5
MW (Da)
1.07
ALogP
8
HBA
3
HBD
130.4
PSA (Ų)
0.43
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C24H32O8
MW 448.51
Aromatic Rings 0
Heavy Atoms 32
NP-Likeness 3.21

Activity Summary

Ki 8 meas. best 9.46
EC50 3 meas. best 6.0
IC50 3 meas. best 5.87

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Protein kinase C delta type
CHEMBL2560
 Ki 9.46 8.1888 0.4 8
Human immunodeficiency virus 2
CHEMBL380
 EC50 6.0 6.0 1000.0 1
Human immunodeficiency virus 1
CHEMBL378
 IC50 5.87 5.87 1360.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 5.32 5.32 4800.0 1
A549
CHEMBL392
 IC50 5.13 5.13 7490.0 1
MDA-MB-231
CHEMBL400
 IC50 5.05 5.05 8910.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.03 5.03 9400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Protein kinase C delta type Ki = 0.351 nM 9.46 Binding of Indolactam-V(ILV) to wild-type Protein kinase C delta C1b domain 10479277
Protein kinase C delta type Ki = 0.82 nM 9.09 Binding of Indolactam-V(ILV) to mutant Protein kinase C delta C1b domain (Phe13 ... 10479277
Protein kinase C delta type Ki = 1.24 nM 8.91 Binding of Indolactam-V(ILV) to mutant Protein kinase C delta C1b domain (Thr12 ... 10479277
Protein kinase C delta type Ki = 6.59 nM 8.18 Binding of Indolactam-V(ILV) to mutant Protein kinase C delta C1b domain (Leu20 ... 10479277
Protein kinase C delta type Ki = 14.2 nM 7.85 Binding of Indolactam-V(ILV) to mutant Protein kinase C delta C1b domain (Gln27 ... 10479277
Protein kinase C delta type Ki = 18.4 nM 7.74 Binding of Indolactam-V(ILV) to mutant Protein kinase C delta C1b domain (Tyr8 t... 10479277
Protein kinase C delta type Ki = 25.0 nM 7.6 Binding of Indolactam-V(ILV) to mutant Protein kinase C delta C1b domain (Trp22 ... 10479277
Protein kinase C delta type Ki = 210.0 nM 6.68 Binding of Indolactam-V(ILV) to mutant Protein kinase C delta C1b domain (Pro11 ... 10479277
Human immunodeficiency virus 2 EC50 = 1000.0 nM 6.0 Antiviral activity against HIV2 ROD infected in MT4 cells assessed as cell viabi... 25970561
Human immunodeficiency virus 1 IC50 = 1360.0 nM 5.87 Antiviral activity against HIV-1 NL4-3 infected in human MT4 cells assessed as r... 34403728
Human immunodeficiency virus 1 EC50 = 4800.0 nM 5.32 Antiviral activity against HIV1 3B infected in MT4 cells assessed as cell viabil... 25970561
A549 IC50 = 7490.0 nM 5.13 Antiproliferative activity against human A549 cells assessed as reduction in cel... 34403728
MDA-MB-231 IC50 = 8910.0 nM 5.05 Antiproliferative activity against human MDA-MB-231 cells assessed as reduction ... 34403728
NON-PROTEIN TARGET EC50 = 9400.0 nM 5.03 Antiviral activity against chikungunya virus Indian ocean strain 899 infected in... 25970561

Literature References

PubMed DOI Target Context # Activities
10479277 10.1021/jm990129n Protein kinase C delta type 23
25970561 10.1021/acs.jnatprod.5b00073 Unchecked 3
33945688 10.1021/acs.jmedchem.1c00156 Unchecked 2
33945688 10.1021/acs.jmedchem.1c00156 Brain 2
25970561 10.1021/acs.jnatprod.5b00073 NON-PROTEIN TARGET 1
25970561 10.1021/acs.jnatprod.5b00073 Human immunodeficiency virus 1 1
25970561 10.1021/acs.jnatprod.5b00073 Human immunodeficiency virus 2 1
34403728 10.1016/j.bmcl.2021.128319 A549 1
34403728 10.1016/j.bmcl.2021.128319 MDA-MB-231 1
34403728 10.1016/j.bmcl.2021.128319 KB 1
34403728 10.1016/j.bmcl.2021.128319 Unchecked 1
34403728 10.1016/j.bmcl.2021.128319 MCF7 1
34403728 10.1016/j.bmcl.2021.128319 Human immunodeficiency virus 1 1
34403728 10.1016/j.bmcl.2021.128319 MT4 1

Data from ChEMBL 36 via Core Engine