ZIRITAXESTAT

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Synonyms
Status
Molecule Category UNKNOWN
UNII I02418V13W

Structure

InChI Key REQQVBGILUTQNN-UHFFFAOYSA-N
Smiles CCc1nc2c(C)cc(N3CCN(CC(=O)N4CC(O)C4)CC3)cn2c1N(C)c1nc(-c2ccc(F)cc2)c(C#N)s1
InChI
InChI=1S/C30H33FN8O2S/c1-4-24-29(35(3)30-34-27(25(14-32)42-30)20-5-7-21(31)8-6-20)39-15-22(13-19(2)28(39)33-24)37-11-9-36(10-12-37)18-26(41)38-16-23(40)17-38/h5-8,13,15,23,40H,4,9-12,16-18H2,1-3H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C30H33FN8O2S
Molecular Weight 588.71
AlogP 3.43
Hydrogen Bond Acceptor 10.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 104.24
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 42.0

Bioactivity

Mechanism of Action Action Reference
Autotaxin inhibitor INHIBITOR Other
Protein: Autotaxin
Description: Ectonucleotide pyrophosphatase/phosphodiesterase family member 2
Organism : Homo sapiens
Q13822 ENSG00000136960
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Phosphodiesterase
- 224-418 - - -
Enzyme
- 0-242 - 15 90
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 15000-15000 - - -
Assay Description Organism Bioactivity Reference
Inhibition of ATX in human plasma assessed as inhibition of LPA production after 2 hrs by LC-MS/MS analysis Homo sapiens 100.0 nM
Inhibition of ATX in rat plasma assessed as inhibition of LPA production after 2 hrs by LC-MS/MS analysis Rattus norvegicus 500.0 nM
Inhibition of ATX in mouse plasma assessed as inhibition of LPA production after 2 hrs by LC-MS/MS analysis Mus musculus 500.0 nM
Inhibition of human ATX using FS3 as substrate preincubated for 30 mins followed by substrate addition measured after 30 mins by fluorescence assay Homo sapiens 0.01 nM
Inhibition of human ATX using lysophosphatidylcholine as substrate preincubated with enzyme followed by substrate addition measured after 30 mins by luminescence assay Homo sapiens 100.0 nM
Inhibition of recombinant human ATX using lysophosphatidylcholine as substrate by choline release assay Homo sapiens 131.0 nM
Inhibition of recombinant mouse ATX using lysophosphatidylcholine as substrate by choline release assay Mus musculus 224.0 nM
Inhibition of ATX in human plasma assessed as inhibition of LPA 18:2 production after 2 hrs by LC-MS/MS analysis relative to control Homo sapiens 90.0 %
Inhibition of ATX (unknown origin) Homo sapiens 100.0 nM
Inhibition of human ATX using LPC (16:0) as substrate after 30 mins by horseradish peroxidase/choline oxidase coupled enzyme based spectrophotometric analysis Homo sapiens 131.0 nM
Inhibition of ATX in mouse plasma assessed as reduction in LPA 18:2 production after 2 hrs by LC-MS/MS analysis Mus musculus 418.0 nM
Inhibition of ATX in rat plasma assessed as reduction in LPA 18:2 production after 2 hrs by LC-MS/MS analysis Rattus norvegicus 542.0 nM
Inhibition of ATX in human plasma assessed as reduction in LPA 18:2 production after 2 hrs by LC-MS/MS analysis Homo sapiens 242.0 nM
In vivo inhibition of ATX in C57BL/6Rj mouse assessed as reduction in LPA 18:2 level in plasma at 3 mg/kg administered as single dose via oral gavage by LC-MS/MS analysis Mus musculus 83.6 %
In vivo inhibition of ATX in C57BL/6Rj mouse assessed as reduction in LPA 18:2 level in plasma at 10 mg/kg administered as single dose via oral gavage by LC-MS/MS analysis Mus musculus 90.9 %
In vivo inhibition of ATX in C57BL/6Rj mouse assessed as reduction in LPA 18:2 level in plasma at 30 mg/kg administered as single dose via oral gavage by LC-MS/MS analysis Mus musculus 95.2 %
In vivo inhibition of ATX in C57BL/6Rj mouse assessed as reduction in LPA 18:2 production at 3 mg/kg administered as single dose via oral gavage after 6 hrs by LC-MS/MS analysis relative to control Mus musculus 50.0 %
Competitive inhibition of human ATX using LPC (16:0) as substrate after 30 mins by Michaelis-Menten plot analysis Homo sapiens 15.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 10.13 %
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 -0.06 % 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 -0.06 %
Inhibition of human ATX by LPC choline release assay Homo sapiens 131.0 nM
Inhibition of human ATX pre-incubated for 45 mins before fluorogenic substrate-3 addition and measured every minute for 30 mins by fluorescence based assay Homo sapiens 1.3 nM
Inhibition of glycosylated human ATX using FS-3 as substrate preincubated for 45 mins followed by substrate addition and measured every 1 min for 30 mins by fluorescence microplate reader assay Homo sapiens 3.1 nM
Inhibition of human C-terminal His6-tagged ATX beta expressed in Sf9 insect cells using FS-3 as substrate preincubated for 45 mins followed by substrate addition and measured at 1 min interval for 30 mins by fluorescence assay Homo sapiens 3.7 nM
Inhibition of human ATX using FS-3 as substrate preincubated for 45 mins followed by substrate addition and measured every 1 min for 30 mins by fluorescence microplate reader assay Homo sapiens 2.9 nM

Cross References

Resources Reference
ChEMBL CHEMBL3828074
DrugBank DB15403
FDA SRS I02418V13W
Guide to Pharmacology 9561
PDB 7NB
PubChem 90420193
SureChEMBL SCHEMBL16051264
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