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Compound Detail

CHEMBL375767

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Cc1cn([C@H]2C=C[C@@H](COP3(=O)OCc4ccccc4O3)O2)c(=O)[nH]c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL375767
Phase Preclinical
Structure Type MOL
InChI Key NEUXRWCLDPVEMR-OHDXJBIGSA-N
4
Targets
15
Activities
2
Assay Types
14
PK Parameters
20
Publications
0
Known Names

Molecular Properties

392.3
MW (Da)
2.03
ALogP
8
HBA
1
HBD
108.8
PSA (Ų)
0.63
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 C17H17N2O7P
MW 392.30
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness 0.40

Activity Summary

EC50 13 meas. best 7.0
IC50 2 meas. best 6.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 EC50 7.0 6.94 100.0 3
Human immunodeficiency virus 2
CHEMBL380
 EC50 6.89 6.5483 130.0 6
CCRF-CEM
CHEMBL382
 EC50 6.55 6.4025 280.0 4
Cholinesterase
CHEMBL1914
 IC50 6.11 6.11 770.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 24.5 hr -
T1/2 4.5 hr -
T1/2 1.1 hr -
T1/2 7.2 hr -
T1/2 3.9 hr -
T1/2 24.5 hr -
T1/2 4.0 hr -
T1/2 1.1 hr -
T1/2 4.4 hr -
T1/2 4.4 hr -
T1/2 4.0 hr Homo sapiens
T1/2 4.4 hr -
T1/2 4.0 hr Homo sapiens
t1/2 - - Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 100.0 nM 7.0 Antiviral activity against HIV1 in CEM/0 cells 17335187
Human immunodeficiency virus 1 EC50 = 100.0 nM 7.0 Antiviral activity against HIV1 in human CEM cells 18826203
Human immunodeficiency virus 2 EC50 = 130.0 nM 6.89 Antiviral activity against H1V2 in CEM/0 cells 17328534
Human immunodeficiency virus 2 EC50 = 130.0 nM 6.89 Antiviral activity against HIV2 ROD in CEM/0 cells 17335187
Human immunodeficiency virus 2 EC50 = 130.0 nM 6.89 Antiviral activity against HIV2 ROD in human CEM cells 18826203
Human immunodeficiency virus 1 EC50 = 150.0 nM 6.82 Antiviral activity against HIV1 in CEM/0 cells 17328534
CCRF-CEM EC50 = 280.0 nM 6.55 Antiviral activity was measured on HIV-1 in wild-type CEM/O cells 9554875
CCRF-CEM EC50 = 280.0 nM 6.55 Anti-HIV-1 activity tested in human lymphocytic CEM cells 15139762
Human immunodeficiency virus 2 EC50 = 300.0 nM 6.52 Antiviral activity against H1V2 in TK-deficient CEM cells 17328534
CCRF-CEM EC50 = 500.0 nM 6.3 Antiviral activity was measured on HIV-2 in mutant thymidine kinase-deficient CE... 9554875
CCRF-CEM EC50 = 620.0 nM 6.21 Antiviral activity was measured on HIV-2 in wild-type CEM/O cells 9554875
Cholinesterase IC50 = 770.0 nM 6.11 Inhibitory activity towards human butyrylcholinesterase 15139762
Cholinesterase IC50 = 770.0 nM 6.11 Inhibition of human serum BChE 17328534
Human immunodeficiency virus 2 EC50 = 900.0 nM 6.05 Antiviral activity against HIV2 ROD in CEM/TK- cells 17335187
Human immunodeficiency virus 2 EC50 = 900.0 nM 6.05 Antiviral activity against HIV2 ROD in thymidine kinase deficient human CEM cell... 18826203

Literature References

PubMed DOI Target Context # Activities
9554875 10.1021/jm970664s ADMET 6
9554875 10.1021/jm970664s CCRF-CEM 4
- 10.1016/S0960-894X(96)00597-5 ADMET 3
- 10.1016/S0960-894X(96)00597-5 CCRF-CEM 3
18826203 10.1021/jm800815b CCRF-CEM 2
18826203 10.1021/jm800815b Human immunodeficiency virus 2 2
17335187 10.1021/jm0613267 Human immunodeficiency virus 2 2
17328534 10.1021/jm0611713 Human immunodeficiency virus 2 2
17328534 10.1021/jm0611713 No relevant target 1
17328534 10.1021/jm0611713 Cholinesterase 1
17328534 10.1021/jm0611713 Human immunodeficiency virus 1 1
- 10.1016/S0960-894X(96)00597-5 No relevant target 1
17328534 10.1021/jm0611713 ADMET 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
15139762 10.1021/jm031032a CCRF-CEM 1
18826203 10.1021/jm800815b Serum 1
15139762 10.1021/jm031032a Cholinesterase 1

Data from ChEMBL 36 via Core Engine