IMPPAT Phytochemical information: 
5-Geranyloxy-7-methoxycoumarin

5-Geranyloxy-7-methoxycoumarin
Summary

SMILES: COc1cc(OC/C=C(/CCC=C(C)C)\C)c2c(c1)oc(=O)cc2
InChI: InChI=1S/C20H24O4/c1-14(2)6-5-7-15(3)10-11-23-18-12-16(22-4)13-19-17(18)8-9-20(21)24-19/h6,8-10,12-13H,5,7,11H2,1-4H3/b15-10+
InChIKey: WXUOSNJWDJOHGW-XNTDXEJSSA-N
DeepSMILES: COcccOC/C=C/CCC=CC)C)))))\C)))))ccc6)oc=O)cc6
Scaffold Graph/Node/Bond level: O=c1ccc2ccccc2o1
Scaffold Graph/Node level: OC1CCC2CCCCC2O1
Scaffold Graph level: CC1CCC2CCCCC2C1
Functional groups: cOC; C/C=C(/C)C; CC=C(C)C; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
5-geranyloxy-7-methoxy coumarin
External chemical identifiers:
CID:CID_6441377; ChEMBL:CHEMBL4176013; ChEBI:CHEBI:174428; ZINC:ZINC000002558139; SureChEMBL:SCHEMBL1714204
Chemical structure download


5-Geranyloxy-7-methoxycoumarin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 328.41
Log P RDKit 4.87
Topological polar surface area (Å2) RDKit 48.67
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
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 13
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2


5-Geranyloxy-7-methoxycoumarin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.54


5-Geranyloxy-7-methoxycoumarin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.60
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No