IMPPAT Phytochemical information: 
Dicumarol

Dicumarol
Summary

SMILES: O=c1oc2ccccc2c(c1Cc1c(=O)oc2c(c1O)cccc2)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
InChIKey: DOBMPNYZJYQDGZ-UHFFFAOYSA-N
DeepSMILES: O=cocccccc6cc%10Ccc=O)occc6O))cccc6)))))))))))O
Scaffold Graph/Node/Bond level: O=c1oc2ccccc2cc1Cc1cc2ccccc2oc1=O
Scaffold Graph/Node level: OC1OC2CCCCC2CC1CC1CC2CCCCC2OC1O
Scaffold Graph level: CC1CC2CCCCC2CC1CC1CC2CCCCC2CC1C
Functional groups: c=O; coc; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Hydroxycoumarins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
dicumarol, dicoumarol
External chemical identifiers:
CID:CID_54676038; ChEMBL:CHEMBL1466; ChEBI:CHEBI:4513; ZINC:ZINC000003869855; FDASRS:7QID3E7BG7; SureChEMBL:SCHEMBL33891; MolPort-000-422-589
Chemical structure download


Dicumarol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 336.3
Log P RDKit 2.9
Topological polar surface area (Å2) RDKit 100.88
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.05
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 4
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Dicumarol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.54591


Dicumarol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.88
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No