IMPPAT Phytochemical information: 
5,6-Dihydroxy-1,3-dimethoxy-9H-xanthen-9-one

5,6-Dihydroxy-1,3-dimethoxy-9H-xanthen-9-one
Summary

SMILES: COc1cc(OC)c2c(c1)oc1c(c2=O)ccc(c1O)O
InChI: InChI=1S/C15H12O6/c1-19-7-5-10(20-2)12-11(6-7)21-15-8(13(12)17)3-4-9(16)14(15)18/h3-6,16,18H,1-2H3
InChIKey: UWYJVMLBMYBZSD-UHFFFAOYSA-N
DeepSMILES: COcccOC))ccc6)occc6=O))cccc6O))O
Scaffold Graph/Node/Bond level: O=c1c2ccccc2oc2ccccc12
Scaffold Graph/Node level: OC1C2CCCCC2OC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CC2CCCCC21
Functional groups: cOC; coc; c=O; 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:
1,3-dimethoxy-5,6-dihydroxyxanthone
External chemical identifiers:
CID:CID_53439039; ChEMBL:CHEMBL3093481; ZINC:ZINC000014764388
Chemical structure download


5,6-Dihydroxy-1,3-dimethoxy-9H-xanthen-9-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 288.26
Log P RDKit 2.37
Topological polar surface area (Å2) RDKit 89.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 21
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 13
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.13
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 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


5,6-Dihydroxy-1,3-dimethoxy-9H-xanthen-9-one
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 0.555629


5,6-Dihydroxy-1,3-dimethoxy-9H-xanthen-9-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -6.50
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No