VADADUSTAT

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Synonyms
Status
Molecule Category UNKNOWN
UNII I60W9520VV

Structure

InChI Key JGRXMPYUTJLTKT-UHFFFAOYSA-N
Smiles O=C(O)CNC(=O)c1ncc(-c2cccc(Cl)c2)cc1O
InChI
InChI=1S/C14H11ClN2O4/c15-10-3-1-2-8(4-10)9-5-11(18)13(16-6-9)14(21)17-7-12(19)20/h1-6,18H,7H2,(H,17,21)(H,19,20)

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H11ClN2O4
Molecular Weight 306.71
AlogP 1.92
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 4.0
Polar Surface Area 99.52
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 21.0

Bioactivity

Mechanism of Action Action Reference
Egl nine homolog 1 inhibitor INHIBITOR Other PubMed PubMed PubMed PubMed
Protein: Hypoxia-inducible factor prolyl hydroxylase 1
Description: Prolyl hydroxylase EGLN2
Organism : Homo sapiens
Q96KS0 ENSG00000269858
Protein: Egl nine homolog 1
Description: Egl nine homolog 1
Organism : Homo sapiens
Q9GZT9 ENSG00000135766
Protein: Egl nine homolog 3
Description: Prolyl hydroxylase EGLN3
Organism : Homo sapiens
Q9H6Z9 ENSG00000129521
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 29-13700 - 280 -
Assay Description Organism Bioactivity Reference
Enzyme Assay: The EGLN-1 (or EGLN-3) enzyme activity is determined using mass spectrometry (matrix-assisted laser desorption ionization, time-of-flight MS, MALDI-TOF MS—for assay details, see reference (Greis et al., 2006). Homo sapiens 410.0 nM
Mass Spectrometry Assay : The EGLN-1 (or EGLN-3) enzyme activity is determined using mass spectrometry (matrix-assisted laser desorption ionization, time-of-flight MS, MALDI-TOF MS—for assay details, see reference (Greis et al, 2006). The reaction is conducted in a total volume of 50 uL containing TrisCl (5 mM, pH7.5), ascorbate (120 μM), 2-oxoglutarate (3.2 μM), HIF-1α (8.6 μM), and bovine serum albumin (0.01%). The enzyme, quantity predetermined to hydroxylate 20% of substrate in 20 minutes, is added to start the reaction. Compounds are prepared in dimethyl sulfoxide at 10-fold final assay concentration. After 20 minutes at room temperature, the reaction is stopped by transferring 10 μL of reaction mixture to 50 μL of a mass spectrometry matrix solution (α-cyano-4-hydroxycinnamic acid, 5 mg/mL in 50% acetonitrile/0.1% TFA, 5 mM NH4PO4). Two microliters of the mixture is spotted onto a MALDI-TOF MS target plate for analysis with an Applied Biosystems. Homo sapiens 410.0 nM
Enzyme Assay: The EGLN-1 (or EGLN-3) enzyme activity is determined using mass spectrometry (matrix-assisted laser desorption ionization, time-of-flight MS, MALDI-TOF MS—for assay details, see reference (Greis et al., 2006). Homo sapiens 390.0 nM
Mass Spectrometry Assay : The EGLN-1 (or EGLN-3) enzyme activity is determined using mass spectrometry (matrix-assisted laser desorption ionization, time-of-flight MS, MALDI-TOF MS—for assay details, see reference (Greis et al, 2006). The reaction is conducted in a total volume of 50 uL containing TrisCl (5 mM, pH7.5), ascorbate (120 μM), 2-oxoglutarate (3.2 μM), HIF-1α (8.6 μM), and bovine serum albumin (0.01%). The enzyme, quantity predetermined to hydroxylate 20% of substrate in 20 minutes, is added to start the reaction. Compounds are prepared in dimethyl sulfoxide at 10-fold final assay concentration. After 20 minutes at room temperature, the reaction is stopped by transferring 10 μL of reaction mixture to 50 μL of a mass spectrometry matrix solution (α-cyano-4-hydroxycinnamic acid, 5 mg/mL in 50% acetonitrile/0.1% TFA, 5 mM NH4PO4). Two microliters of the mixture is spotted onto a MALDI-TOF MS target plate for analysis with an Applied Biosystems. Homo sapiens 390.0 nM
Inhibition of recombinant human HIF-PHD2 using DLDLEALAPYIPADDDFQL as substrate after 20 mins by mass spectrometry Homo sapiens 390.0 nM
Inhibition of N-terminal His6-tagged recombinant Paramecium bursaria chlorella virus 1 CPH expressed in Escherichia coli Rosetta 2 (DE3) cells pre-incubated for 5 mins before 2OG as substrate and Fe2 as co-factor addition in presence of L-ascorbate and measured after 5 mins MALDI TOF MS analysis Paramecium bursaria Chlorella virus 1 280.0 nM
Inhibition of recombinant human PHD2 using 2OG as substrate and Fe2 as co-factor assessed as hydroxylation incubated for 15 mins in presence of L-ascorbate by LC-MS analysis Homo sapiens 29.0 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 4.97 %
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 -0.01 % 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 -0.01 %

Cross References

Resources Reference
ChEMBL CHEMBL3646221
DrugBank DB12255
FDA SRS I60W9520VV
PDB A1Z
PubChem 23634441
SureChEMBL SCHEMBL1920738
ZINC ZINC000117532869
CONTENTS