IMPPAT Phytochemical information: 
1,7-Dihydroxy-3-methoxy-2-prenylxanthone

1,7-Dihydroxy-3-methoxy-2-prenylxanthone
Summary

SMILES: COc1cc2oc3ccc(cc3c(=O)c2c(c1CC=C(C)C)O)O
InChI: InChI=1S/C19H18O5/c1-10(2)4-6-12-15(23-3)9-16-17(18(12)21)19(22)13-8-11(20)5-7-14(13)24-16/h4-5,7-9,20-21H,6H2,1-3H3
InChIKey: JKOMBLYQDHTFJC-UHFFFAOYSA-N
DeepSMILES: COcccocccccc6c=O)c%10cc%14CC=CC)C)))))O))))))O
Scaffold Graph/Node/Bond level: O=c1c2ccccc2oc2ccccc12
Scaffold Graph/Node level: OC1C2CCCCC2OC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CC2CCCCC21
Functional groups: cOC; coc; c=O; CC=C(C)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Xanthones
NP Classifier Class: Plant xanthones
Synonymous chemical names:
2-(γ, γ-dimethylallyl)-1,7-dihydroxy-3-methoxyxanthone
External chemical identifiers:
CID:CID_509269; ChEMBL:CHEMBL454581; ChEBI:CHEBI:175158; ZINC:ZINC000014819753; SureChEMBL:SCHEMBL2050831; MolPort-023-299-051
Chemical structure download


1,7-Dihydroxy-3-methoxy-2-prenylxanthone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 326.35
Log P RDKit 3.87
Topological polar surface area (Å2) RDKit 79.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 5
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 15
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 3
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 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3


1,7-Dihydroxy-3-methoxy-2-prenylxanthone
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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.56


1,7-Dihydroxy-3-methoxy-2-prenylxanthone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.95
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 No
P-glycoprotein substrate SwissADME No