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Compound Detail

CHEMBL259011

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COc1cccc2c1c(C(=O)/C=C(\O)C(=O)O)cn2Cc1ccc(F)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL259011
Phase Preclinical
Structure Type MOL
InChI Key GSMHULZNHJSXPP-MFOYZWKCSA-N
6
Targets
43
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

369.4
MW (Da)
3.55
ALogP
5
HBA
2
HBD
88.8
PSA (Ų)
0.39
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H16FNO5
MW 369.35
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -0.58

Activity Summary

EC50 29 meas. best 6.52
IC50 14 meas. best 7.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus type 1 integrase
CHEMBL3471
 IC50 7.1 6.9509 80.0 11
Human immunodeficiency virus 1
CHEMBL378
 EC50 6.52 6.1528 300.0 25
Human immunodeficiency virus 2
CHEMBL380
 EC50 5.75 5.715 1760.0 2
Simian immunodeficiency virus
CHEMBL613499
 EC50 5.32 5.32 4760.0 1
Unchecked
CHEMBL612545
 IC50 4.44 4.44 36000.0 2
MT4
CHEMBL388
 EC50 4.39 4.39 41100.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 11.0 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus type 1 integrase IC50 = 80.0 nM 7.1 Inhibition of HIV-1 integrase after 1 hr by ELISA 21227550
Human immunodeficiency virus type 1 integrase IC50 = 80.0 nM 7.1 Inhibition of HIV1 integrase 20630765
Human immunodeficiency virus type 1 integrase IC50 = 80.0 nM 7.1 Inhibition of HIV1 integrase activity by ELISA 19105658
Human immunodeficiency virus type 1 integrase IC50 = 80.0 nM 7.1 Inhibition of HIV1 integrase 18417342
Human immunodeficiency virus type 1 integrase IC50 = 110.0 nM 6.96 Inhibition of Human immunodeficiency virus 1 integrase 18541726
Human immunodeficiency virus type 1 integrase IC50 = 140.0 nM 6.85 Inhibition of HIV-1 integrase strand transfer activity using 3'-end biotin label... 24618511
Human immunodeficiency virus type 1 integrase IC50 = 140.0 nM 6.85 Inhibition of HIV-1 integrase strand transfer activity 25462257
Human immunodeficiency virus type 1 integrase IC50 = 140.0 nM 6.85 Inhibition of Human immunodeficiency virus 1 integrase strand transfer activity 18541726
Human immunodeficiency virus type 1 integrase IC50 = 140.0 nM 6.85 Inhibition of HIV1 integrase strand transfer 20630765
Human immunodeficiency virus type 1 integrase IC50 = 140.0 nM 6.85 Inhibition of HIV1 integrase strand transfer activity by ELISA 19105658
Human immunodeficiency virus type 1 integrase IC50 = 140.0 nM 6.85 Inhibition of HIV1 integrase strand transfer activity 18417342
Human immunodeficiency virus 1 EC50 = 300.0 nM 6.52 Antiviral activity against R5 tropic Human immunodeficiency virus 1 BAL infected... 18541726
Human immunodeficiency virus 1 EC50 = 300.0 nM 6.52 Antiviral activity against X4 tropic Human immunodeficiency virus 1 3B infected ... 18541726
Human immunodeficiency virus 1 EC50 = 320.0 nM 6.5 Antiviral activity against HIV 1 NL4.3 harboring integrase L74M mutant infected ... 18378713
Human immunodeficiency virus 1 EC50 = 390.0 nM 6.41 Antiviral activity against HIV 1 3B infected in MT-4 cells assessed as inhibitio... 18378713
Human immunodeficiency virus 1 EC50 = 440.0 nM 6.36 Antiviral activity against HIV 1 RIN harboring integrase gene infected in MT-4 c... 18378713
Human immunodeficiency virus 1 EC50 = 490.0 nM 6.31 Antiviral activity against HIV 1 NL4.3 integrase S230N mutant infected in human ... 18378713
Human immunodeficiency virus 1 EC50 = 520.0 nM 6.28 Antiviral activity against HIV 1 RIN harboring integrase gene infected in MT-4 c... 18378713
Human immunodeficiency virus 1 EC50 = 560.0 nM 6.25 Antiviral activity against HIV 1 NL4.3 assessed as inhibition of virus-induced c... 18378713
Human immunodeficiency virus 1 EC50 = 590.0 nM 6.23 Antiviral activity against HIV1 3B infected in human MT4 cells assessed as inhib... 21227550

Literature References

PubMed DOI Target Context # Activities
18541726 10.1128/aac.00210-08 Human immunodeficiency virus 1 16
18378713 10.1128/aac.00911-07 Human immunodeficiency virus 1 12
18541726 10.1128/aac.00210-08 Human immunodeficiency virus 7
18541726 10.1128/aac.00210-08 Unchecked 2
18541726 10.1128/aac.00210-08 Human immunodeficiency virus 2 2
19105658 10.1021/jm8009266 Human immunodeficiency virus type 1 integrase 2
18541726 10.1128/aac.00210-08 Human immunodeficiency virus type 1 integrase 2
20630765 10.1016/j.bmc.2010.06.063 Human immunodeficiency virus type 1 integrase 2
24618511 10.1016/j.bmc.2014.02.012 Unchecked 2
18417342 10.1016/j.bmcl.2008.03.089 Human immunodeficiency virus type 1 integrase 2
21227550 10.1016/j.ejmech.2010.12.012 Human immunodeficiency virus type 1 integrase 2
20630765 10.1016/j.bmc.2010.06.063 MT4 1
21227550 10.1016/j.ejmech.2010.12.012 MT4 1
20630765 10.1016/j.bmc.2010.06.063 Unchecked 1
27810600 10.1016/j.ejmech.2016.10.030 Mushroom tyrosinase 1
19105658 10.1021/jm8009266 Unchecked 1
19105658 10.1021/jm8009266 MT4 1
19105658 10.1021/jm8009266 Human immunodeficiency virus 1 1
18417342 10.1016/j.bmcl.2008.03.089 Unchecked 1
18417342 10.1016/j.bmcl.2008.03.089 MT4 1

Data from ChEMBL 36 via Core Engine