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Compound Detail

CHEMBL376065

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Cc1cccc2c1OP(=O)(OC[C@@H]1C=C[C@H](n3cc(C)c(=O)[nH]c3=O)O1)OC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL376065
Phase Preclinical
Structure Type MOL
InChI Key OVLSREDRLCJLHH-BIGJLOMDSA-N
6
Targets
19
Activities
2
Assay Types
9
PK Parameters
15
Publications
0
Known Names

Molecular Properties

406.3
MW (Da)
2.34
ALogP
8
HBA
1
HBD
108.8
PSA (Ų)
0.61
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H19N2O7P
MW 406.33
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness 0.38

Activity Summary

EC50 18 meas. best 7.96
IC50 1 meas. best 5.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MT4
CHEMBL388
 EC50 7.96 7.7275 11.0 4
Human immunodeficiency virus 2
CHEMBL380
 EC50 7.3 7.23 50.0 2
Human immunodeficiency virus 1
CHEMBL378
 EC50 7.22 7.22 60.0 1
CCRF-CEM
CHEMBL382
 EC50 7.2 6.804 63.0 10
Human immunodeficiency virus
CHEMBL613758
 EC50 7.0 7.0 100.0 1
Cholinesterase
CHEMBL1914
 IC50 5.92 5.92 1200.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 68.5 hr -
T1/2 10.2 hr -
T1/2 1.5 hr -
T1/2 16.0 hr -
T1/2 9.1 hr -
T1/2 17.5 hr -
T1/2 14.5 hr Homo sapiens
T1/2 17.5 hr -
T1/2 15.0 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MT4 EC50 = 11.0 nM 7.96 Antiviral activity was measured on HIV-2 in MT-4 cells for R configuration 9554875
MT4 EC50 = 12.0 nM 7.92 Antiviral activity was measured on HIV-1 in MT-4 cells for R configuration 9554875
MT4 EC50 = 28.0 nM 7.55 Antiviral activity was measured on HIV-1 in MT-4 cells 9554875
MT4 EC50 = 33.0 nM 7.48 Antiviral activity was measured on HIV-2 in MT-4 cells 9554875
Human immunodeficiency virus 2 EC50 = 50.0 nM 7.3 Antiviral activity against HIV2 ROD in CEM/TK- cells 17335187
Human immunodeficiency virus 1 EC50 = 60.0 nM 7.22 Antiviral activity against HIV1 in CEM/0 cells 17335187
CCRF-CEM EC50 = 63.0 nM 7.2 Antiviral activity was measured on HIV-2 in mutant thymidine kinase-deficient CE... 9554875
CCRF-CEM EC50 = 67.0 nM 7.17 Antiviral activity was measured on HIV-2 in wild-type CEM/O cells for R configur... 9554875
Human immunodeficiency virus 2 EC50 = 70.0 nM 7.16 Antiviral activity against HIV2 ROD in CEM/0 cells 17335187
CCRF-CEM EC50 = 80.0 nM 7.1 Antiviral activity was measured on HIV-1 in wild-type CEM/O cells for R configur... 9554875
CCRF-CEM EC50 = 87.0 nM 7.06 Antiviral activity was measured on HIV-1 in wild-type CEM/O cells 9554875
CCRF-CEM EC50 = 87.0 nM 7.06 Anti-HIV-1 activity tested in human lymphocytic CEM cells 15139762
CCRF-CEM EC50 = 93.0 nM 7.03 Antiviral activity was measured on HIV-2 in mutant thymidine kinase-deficient CE... 9554875
Human immunodeficiency virus EC50 = 100.0 nM 7.0 Antiviral activity against HIV 18834186
CCRF-CEM EC50 = 120.0 nM 6.92 Antiviral activity was measured on HIV-2 in wild-type CEM/O cells 9554875
CCRF-CEM EC50 = 420.0 nM 6.38 Antiviral activity was measured on HIV-1 in wild-type CEM/O cells for S configur... 9554875
CCRF-CEM EC50 = 700.0 nM 6.16 Antiviral activity was measured on HIV-2 in mutant thymidine kinase-deficient CE... 9554875
CCRF-CEM EC50 = 1100.0 nM 5.96 Antiviral activity was measured on HIV-2 in wild-type CEM/O cells for S configur... 9554875
Cholinesterase IC50 = 1200.0 nM 5.92 Inhibitory activity towards human butyrylcholinesterase 15139762

Literature References

PubMed DOI Target Context # Activities
9554875 10.1021/jm970664s CCRF-CEM 12
9554875 10.1021/jm970664s ADMET 6
9554875 10.1021/jm970664s MT4 4
17335187 10.1021/jm0613267 Human immunodeficiency virus 2 2
15139762 10.1021/jm031032a Acetylcholinesterase 1
15139762 10.1021/jm031032a Cholinesterase 1
15139762 10.1021/jm031032a CCRF-CEM 1
17335187 10.1021/jm0613267 No relevant target 1
17335187 10.1021/jm0613267 ADMET 1
17335187 10.1021/jm0613267 Serum 1
17335187 10.1021/jm0613267 Human immunodeficiency virus 1 1
17335187 10.1021/jm0613267 CCRF-CEM 1
18834186 10.1021/jm800853p Human immunodeficiency virus 1
18834186 10.1021/jm800853p No relevant target 1
19438207 10.1021/jm900164g No relevant target 1

Data from ChEMBL 36 via Core Engine