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Compound Detail

CHEMBL1466

DICUMAROL
💊 Approved Drug
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💊 Approved Drug
O=c1oc2ccccc2c(O)c1Cc1c(O)c2ccccc2oc1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1466
Name DICUMAROL
Phase Approved
Structure Type MOL
InChI Key DOBMPNYZJYQDGZ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Bishydroxycoumarin Dicoumarol Dicoumarolum Dicumarol NSC-17860 NSC-221570 NSC-41834
14
Targets
32
Activities
4
Assay Types
0
PK Parameters
20
Publications
7
Known Names
1
Indications
1
Mechanisms

Molecular Properties

336.3
MW (Da)
2.90
ALogP
6
HBA
2
HBD
100.9
PSA (Ų)
0.55
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1944
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -arol
USAN Year 1971

Extended Properties

Molecular Formula C19H12O6
MW 336.30
Aromatic Rings 4
Heavy Atoms 25
NP-Likeness 0.33

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Vitamin k epoxide reductase complex subunit 1 isoform 1 inhibitor INHIBITOR Vitamin K epoxide reductase complex subunit 1 ✓ ✓

Indications

Thrombosis

ATC Classification

B01AA01
dicoumarol
Level 1: BLOOD AND BLOOD FORMING ORGANS
Level 2: ANTITHROMBOTIC AGENTS

Activity Summary

IC50 22 meas. best 8.59
Ki 6 meas. best 9.0
EC50 3 meas. best 5.89
Kd 1 meas. best 4.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NAD(P)H dehydrogenase [quinone] 1
CHEMBL3091269
 Ki 9.0 9.0 1.0 1
NAD(P)H dehydrogenase [quinone] 1
CHEMBL3623
 IC50 8.59 7.0733 2.6 6
G-protein coupled receptor 35
CHEMBL1293267
 Ki 7.41 7.41 39.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 6.52 6.52 300.0 1
Cytochrome P450 2C9
CHEMBL3397
 Ki 6.22 5.97 600.0 2
Proprotein convertase subtilisin/kexin type 7
CHEMBL2232
 IC50 5.89 5.89 1300.0 1
G-protein coupled receptor 35
CHEMBL1293267
 EC50 5.89 5.5967 1300.0 3
Unchecked
CHEMBL612545
 IC50 5.51 5.2233 3100.0 3
Aldo-keto reductase family 1 member B1
CHEMBL2622
 IC50 5.39 5.39 4093.0 1
Mitogen-activated protein kinase 1
CHEMBL4040
 IC50 5.35 5.35 4426.0 1
Urease
CHEMBL4161
 IC50 4.82 4.82 15010.0 2
HCT-116
CHEMBL394
 IC50 4.72 4.72 19000.0 1
Unchecked
CHEMBL612545
 Kd 4.66 4.66 22000.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.4 4.4 39930.0 1
Enoyl-[acyl-carrier-protein] reductase [NADH]
CHEMBL2150835
 IC50 4.33 4.33 47000.0 1
Unchecked
CHEMBL612545
 Ki 4.3 4.3 50000.0 1
MIA PaCa-2
CHEMBL614725
 IC50 4.28 4.15 52000.0 3
ATP phosphoribosyltransferase
CHEMBL6086
 Ki 4.22 4.22 60000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NAD(P)H dehydrogenase [quinone] 1 Ki = 1.0 nM 9.0 Competitive binding affinity to rat liver NQO1 in presence of NADPH 29712428
NAD(P)H dehydrogenase [quinone] 1 IC50 = 2.6 nM 8.59 Inhibition of human recombinant NQO1 19877692
NAD(P)H dehydrogenase [quinone] 1 IC50 = 5.0 nM 8.3 Inhibition of human recombinant NQO1 17999461
G-protein coupled receptor 35 Ki = 39.0 nM 7.41 Displacement of [3H]PSB-13253 from human recombinant GPR35 exprssed in CHO cells... 23888932
Cytochrome P450 2C9 IC50 = 300.0 nM 6.52 DRUGMATRIX: CYP450, 2C9 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
NAD(P)H dehydrogenase [quinone] 1 IC50 = 350.0 nM 6.46 Inhibition of recombinant human NQO1 assessed as reduction in oxidation of NADPH... 27829520
NAD(P)H dehydrogenase [quinone] 1 IC50 = 404.0 nM 6.39 Inhibition of human recombinant NQO1 in presence of BSA 19877692
NAD(P)H dehydrogenase [quinone] 1 IC50 = 450.0 nM 6.35 Inhibition of human recombinant NQO1 17011189
NAD(P)H dehydrogenase [quinone] 1 IC50 = 450.0 nM 6.35 Inhibition of human recombinant NQO1 in presence of BSA 17999461
Cytochrome P450 2C9 Ki = 600.0 nM 6.22 Binding affinity was measured on Cytochrome P450 2C9 10956186
Proprotein convertase subtilisin/kexin type 7 IC50 = 1300.0 nM 5.89 Inhibition of recombinant type 8 subtilisin using Arg-Glu-(EDANS)- Ser-Gln-Asn-T... 21510613
G-protein coupled receptor 35 EC50 = 1300.0 nM 5.89 Agonist activity at human GPR35 expressed in HEK293T cells at 5 uM by EYPF-based... 23888932
G-protein coupled receptor 35 EC50 = 1300.0 nM 5.89 Agonist activity at human GPR35 expressed in CHO-K1 cells after 90 mins by beta-... 27976894
Cytochrome P450 2C9 Ki = 1900.0 nM 5.72 Binding affinity towards cytochrome P450 2C9 14761192
Unchecked IC50 = 3100.0 nM 5.51 Inhibition of rat microsomal VKER 17275317
Aldo-keto reductase family 1 member B1 IC50 = 4093.0 nM 5.39 DRUGMATRIX: Aldose Reductase enzyme inhibition (substrate: DL-Glyceraldehyde) -
Mitogen-activated protein kinase 1 IC50 = 4426.0 nM 5.35 DRUGMATRIX: Protein Serine/Threonine Kinase, ERK2 enzyme inhibition (substrate: ... -
Unchecked IC50 = 4570.0 nM 5.34 Inhibition of pepsin from porcine gastric mucosa using Arg-Glu-(EDANS)- Ser-Gln-... 21510613
G-protein coupled receptor 35 EC50 = 9780.0 nM 5.01 Agonist activity at C-terminal beta-galactosidase tagged human recombinant GPR35... 23888932
Urease IC50 = 15135.61 nM 4.82 Inhibition of jack bean urease 18280742

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 461
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
23306152 10.3390/ijms14011293 Aspergillus fumigatus 5
20869876 10.1016/j.bmc.2010.08.052 Albumin 4
23306152 10.3390/ijms14011293 Aspergillus flavus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
23888932 10.1021/jm4009373 G-protein coupled receptor 35 4
17999461 10.1021/jm070472p MIA PaCa-2 4
24308627 10.1021/jm4017448 Rattus norvegicus 3
20014752 10.1021/tx900326k Hepatotoxicity 3
27829520 10.1016/j.ejmech.2016.10.062 NAD(P)H dehydrogenase [quinone] 1 3
9003523 10.1021/jm960450v Human immunodeficiency virus type 1 integrase 3
17999461 10.1021/jm070472p NAD(P)H dehydrogenase [quinone] 1 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 2
27341379 10.1016/j.ejmech.2016.06.019 PC-3 2
19877692 10.1021/jm9011609 NAD(P)H dehydrogenase [quinone] 1 2
19877692 10.1021/jm9011609 MIA PaCa-2 2
19877692 10.1021/jm9011609 HCT-116 2

Data from ChEMBL 36 via Core Engine