IMPPAT Phytochemical information: 
9H-Xanthen-9-one, 1-hydroxy-3,5,6-trimethoxy-

9H-Xanthen-9-one, 1-hydroxy-3,5,6-trimethoxy-
Summary

SMILES: COc1cc(O)c2c(c1)oc1c(c2=O)ccc(c1OC)OC
InChI: InChI=1S/C16H14O6/c1-19-8-6-10(17)13-12(7-8)22-15-9(14(13)18)4-5-11(20-2)16(15)21-3/h4-7,17H,1-3H3
InChIKey: MNLGBRDSLUAKRO-UHFFFAOYSA-N
DeepSMILES: COcccO)ccc6)occc6=O))cccc6OC)))OC
Scaffold Graph/Node/Bond level: O=c1c2ccccc2oc2ccccc12
Scaffold Graph/Node level: OC1C2CCCCC2OC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CC2CCCCC21
Functional groups: cOC; cO; coc; c=O
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-hydroxy-3,5,6-trimethoxyxanthone
External chemical identifiers:
CID:CID_5378599; SureChEMBL:SCHEMBL7933844
Chemical structure download


9H-Xanthen-9-one, 1-hydroxy-3,5,6-trimethoxy-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 302.28
Log P RDKit 2.68
Topological polar surface area (Å2) RDKit 78.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 22
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 3
Shape complexity RDKit 0.19
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


9H-Xanthen-9-one, 1-hydroxy-3,5,6-trimethoxy-
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.75


9H-Xanthen-9-one, 1-hydroxy-3,5,6-trimethoxy-
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.96
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No