IMPPAT Phytochemical information: 
3,8-Dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid

3,8-Dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid
Summary

SMILES: Oc1cc2oc3cc(C)cc(c3c(=O)c2c(c1)C(=O)O)O
InChI: InChI=1S/C15H10O6/c1-6-2-9(17)13-10(3-6)21-11-5-7(16)4-8(15(19)20)12(11)14(13)18/h2-5,16-17H,1H3,(H,19,20)
InChIKey: XSPSQSXYKJASKD-UHFFFAOYSA-N
DeepSMILES: OcccocccC)ccc6c=O)c%10cc%14)C=O)O))))))O
Scaffold Graph/Node/Bond level: O=c1c2ccccc2oc2ccccc12
Scaffold Graph/Node level: OC1C2CCCCC2OC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CC2CCCCC21
Functional groups: cO; coc; c=O; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Xanthones
NP Classifier Class: Methyl xanthones
Synonymous chemical names:
1-hydroxy-6-methoxy-3-methylxanthone-8-carboxylic acid (calyxanthone), calyxanthone
External chemical identifiers:
CID:CID_23902332; ChEMBL:CHEMBL4438577; ZINC:ZINC000013335390; MolPort-006-668-161
Chemical structure download


3,8-Dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 286.24
Log P RDKit 2.36
Topological polar surface area (Å2) RDKit 107.97
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
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 14
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.07
Number of rotatable bonds RDKit 1
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


3,8-Dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid
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 0.59


3,8-Dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.14
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No