IMPPAT Phytochemical information: 
1-Hydroxy-2,3,5-trimethoxyxanthen-9-one

1-Hydroxy-2,3,5-trimethoxyxanthen-9-one
Summary

SMILES: COc1cc2oc3c(OC)cccc3c(=O)c2c(c1OC)O
InChI: InChI=1S/C16H14O6/c1-19-9-6-4-5-8-13(17)12-10(22-15(8)9)7-11(20-2)16(21-3)14(12)18/h4-7,18H,1-3H3
InChIKey: FFVKXGZKJBHJMS-UHFFFAOYSA-N
DeepSMILES: COcccoccOC))cccc6c=O)c%10cc%14OC)))O
Scaffold Graph/Node/Bond level: O=c1c2ccccc2oc2ccccc12
Scaffold Graph/Node level: OC1C2CCCCC2OC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CC2CCCCC21
Functional groups: c=O; cO; cOC; coc
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,2,3,5-trimethoxyxanthone
External chemical identifiers:
CID:5318372; ZINC:ZINC000014764110; SureChEMBL:SCHEMBL18240045; MolPort-039-063-550
Chemical structure download


1-Hydroxy-2,3,5-trimethoxyxanthen-9-one
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


1-Hydroxy-2,3,5-trimethoxyxanthen-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 0.7494


1-Hydroxy-2,3,5-trimethoxyxanthen-9-one
ADMET 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 0.0
Number of Brenk structural alerts SwissADME 1.0
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


1-Hydroxy-2,3,5-trimethoxyxanthen-9-one
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000301141CYP2A6700
ENSP00000324648CYP2B6700
ENSP00000337915CYP3A4700
ENSP00000342007CYP1A2700
ENSP00000360317CYP2C8700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.