DICUMAROL

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
UNII 7QID3E7BG7
EPA CompTox DTXSID8021729

Structure

InChI Key DOBMPNYZJYQDGZ-UHFFFAOYSA-N
Smiles O=c1oc2ccccc2c(O)c1Cc1c(O)c2ccccc2oc1=O
InChI
InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H12O6
Molecular Weight 336.3
AlogP 2.9
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 100.88
Molecular species ACID
Aromatic Rings 4.0
Heavy Atoms 25.0

Bioactivity

Mechanism of Action Action Reference
Vitamin k epoxide reductase complex subunit 1 isoform 1 inhibitor INHIBITOR PubMed
Protein: Vitamin k epoxide reductase complex subunit 1 isoform 1
Description: Vitamin K epoxide reductase complex subunit 1
Organism : Homo sapiens
Q9BQB6 ENSG00000167397
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - 600-1900 -
Enzyme Hydrolase
- 15136 - - 12
Enzyme Oxidoreductase
- 3-450 - 1 81-93
Enzyme Protease Serine protease Serine protease SB clan Serine protease S8B subfamily
- 1300 - - -
Enzyme Transferase
- - - 60000 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Carboxylic acid receptor Kynurenic acid receptor
1300-9780 - - 39 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 19
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 39930 - - -
Assay Description Organism Bioactivity Reference
Binding affinity was measured on Cytochrome P450 2C9 None 600.0 nM
Inhibition of human recombinant NQO1 Homo sapiens 450.0 nM
Inhibition of human recombinant NQO1 Homo sapiens 5.0 nM
Inhibition of human recombinant NQO1 in presence of BSA Homo sapiens 450.0 nM
Inhibition of Strongylocentrotus purpuratus embryos cleavage at 10 uM Strongylocentrotus purpuratus 50.0 %
Inhibition of human recombinant NQO1 Homo sapiens 2.6 nM
Inhibition of human recombinant NQO1 in presence of BSA Homo sapiens 404.0 nM
DRUGMATRIX: CYP450, 2C9 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 300.0 nM
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method Electrophorus electricus 12.27 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method Equus caballus 5.48 %
Displacement of [3H]PSB-13253 from human recombinant GPR35 exprssed in CHO cells by liquid scintillation counting analysis Homo sapiens 39.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 33.08 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 19.32 %
Competitive binding affinity to rat liver NQO1 in presence of NADPH Rattus norvegicus 1.0 nM
Inhibition of recombinant human NQO1 assessed as reduction in oxidation of NADPH to NADP+ at 10 uM using b-lap as substrate and NADPH in presence of 0.14% (w/v) BSA Homo sapiens 81.2 %
Inhibition of recombinant human NQO1 assessed as reduction in oxidation of NADPH to NADP+ using b-lap as substrate and NADPH in presence of 0.14% (w/v) BSA Homo sapiens 350.0 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 -10.08 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 16.75 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.01 %
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 0.32 % 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 0.02 % 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 0.32 % 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 0.02 %
Inhibition of recombinant human C-terminal His-tagged NQO1 (1 to 274 residues) expressed in Escherichia coli assessed as cytochrome c reduction at 25 uM using menadione as substrate in presence of NADPH by spectrophotometry relative to control Homo sapiens 92.5 %

Related Entries

Cross References

Resources Reference
ChEBI 4513
ChEMBL CHEMBL1466
DrugBank DB00266
DrugCentral 867
FDA SRS 7QID3E7BG7
Human Metabolome Database HMDB0014411
Guide to Pharmacology 6808
KEGG C00796
PDB DTC
PubChem 54676038
SureChEMBL SCHEMBL33891
ZINC ZINC000003869855
CONTENTS