Synonyms
Status
Molecule Category Free-form
ATC M01AH06
UNII V91T9204HU
EPA CompTox DTXSID9049035

Structure

InChI Key KHPKQFYUPIUARC-UHFFFAOYSA-N
Smiles Cc1ccc(Nc2c(F)cccc2Cl)c(CC(=O)O)c1
InChI
InChI=1S/C15H13ClFNO2/c1-9-5-6-13(10(7-9)8-14(19)20)18-15-11(16)3-2-4-12(15)17/h2-7,18H,8H2,1H3,(H,19,20)

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H13ClFNO2
Molecular Weight 293.73
AlogP 4.16
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 49.33
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 20.0

Bioactivity

Mechanism of Action Action Reference
Cyclooxygenase-2 inhibitor INHIBITOR PubMed PubMed PubMed
Protein: Cyclooxygenase-2

Description: Prostaglandin G/H synthase 2

Organism : Homo sapiens

P35354 ENSG00000073756
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 7-140 - 320 15-100
Assay Description Organism Bioactivity Reference
Inhibition of COX2 None 7.0 nM
Inhibition of human COX2 for 17 mins pre-incubated before addition of [1-14C]arachidonic acid Homo sapiens 50.0 % Inhibition of human COX2 for 17 mins pre-incubated before addition of [1-14C]arachidonic acid Homo sapiens 107.0 nM
Inhibition of ovine COX1 at 4 uM for 17 mins pre-incubated before addition of [1-14C]arachidonic acid Ovis aries 20.0 %
Inhibition of mouse COX2 at 4 uM for 17 mins pre-incubated before addition of [1-14C]arachidonic acid Mus musculus 20.0 %
Inhibition of mouse COX2 for 20 mins pre-incubated before addition of [1-14C]arachidonic acid Mus musculus 15.0 %
Inhibition of human COX2 for 20 mins pre-incubated before addition of [1-14C]arachidonic acid Homo sapiens 50.0 %
Inhibition of human COX2 mediated PGE2 production in IL-1-beta-induced human dermal fibroblast cells Homo sapiens 130.0 nM
Inhibition of human COX2 mediated PGE2 production in human whole blood Homo sapiens 140.0 nM
Inhibition of mouse COX2 at 4000 nM for 3 mins pre-incubated before addition of [1-14C]arachidonic acid Mus musculus 100.0 %
Inhibition of mouse COX2 at 1 uM for 3 mins pre-incubated before addition of [1-14C]arachidonic acid Mus musculus 15.0 %
Inhibition of human COX2 at 1 uM for 3 mins pre-incubated before addition of [1-14C]arachidonic acid Homo sapiens 50.0 %
Inhibition of human COX2 preincubated before addition of [1-14C]arachidonic acid Homo sapiens 320.0 nM
Inhibition of mouse COX2 V349I mutant pre-incubated before addition of [1-14C]arachidonic acid Mus musculus 20.0 % Inhibition of mouse COX2 V349I mutant pre-incubated before addition of [1-14C]arachidonic acid Mus musculus 750.0 nM
Inhibition of mouse COX2 V349I mutant 20 mins preincubated before addition of [1-14C]arachidonic acid Mus musculus 114.0 nM
Inhibition of mouse COX2 V349I mutant at 4 uM 20 mins pre-incubated before addition of [1-14C]arachidonic acid Mus musculus 75.0 %
Inhibition of mouse COX2 V349L mutant at 4 uM 20 mins pre-incubated before addition of [1-14C]arachidonic acid Mus musculus 20.0 %
Inhibition of mouse COX2 at 4 uM 20 mins pre-incubated before addition of [1-14C]arachidonic acid Mus musculus 20.0 %
Inhibition of COX1 None 7.0 nM
Inhibition of purified mouse COX-2 assessed as inhibition of PGE2/PGD2 formation preincubated at 10 uM for 3 mins before arachidonic acid substrate addition measured after 30 seconds by LC-MS-MS method Mus musculus 25.0 %
Inhibition of purified mouse COX-2 assessed as inhibition of PGE2-G/PGD2-G formation preincubated for 3 mins before 2-AG substrate addition measured after 30 seconds by LC-MS-MS method Mus musculus 40.0 nM
Inhibition of COX2 (unknown origin) Homo sapiens 140.0 nM
Inhibition of COX-2 (unknown origin) Homo sapiens 60.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 6.31 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 22.27 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.73 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 3.313 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.27 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.14 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.08 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.27 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.14 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.08 %

Related Entries

Cross References

Resources Reference
ChEBI 73044
ChEMBL CHEMBL404108
DrugBank DB01283
DrugCentral 1618
FDA SRS V91T9204HU
Human Metabolome Database HMDB0015403
Guide to Pharmacology 2897
PDB LUR
PharmGKB PA164769031
PubChem 151166
SureChEMBL SCHEMBL4479
ZINC ZINC000000007563