IMPPAT Phytochemical information: 
BR-xanthone A

BR-xanthone A
Summary

SMILES: Oc1cc2oc3cc4OC(C)(C)CCc4c(c3c(=O)c2c2c1OC(C)(C)CC2)O
InChI: InChI=1S/C23H24O6/c1-22(2)7-5-11-14(28-22)10-16-18(19(11)25)20(26)17-12-6-8-23(3,4)29-21(12)13(24)9-15(17)27-16/h9-10,24-25H,5-8H2,1-4H3
InChIKey: QFURCBFEIGTKCW-UHFFFAOYSA-N
DeepSMILES: OcccocccOCC)C)CCc6cc%10c=O)c%14cc%18OCC)C)CC6)))))))))O
Scaffold Graph/Node/Bond level: O=c1c2cc3c(cc2oc2ccc4c(c12)CCCO4)OCCC3
Scaffold Graph/Node level: OC1C2CC3CCCOC3CC2OC2CCC3OCCCC3C21
Scaffold Graph level: CC1C2CC3CCCCC3CC2CC2CCC3CCCCC3C21
Functional groups: cO; coc; 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: Methyl xanthones|Plant xanthones
Synonymous chemical names:
br-xanthone a
External chemical identifiers:
CID:CID_13964005; ChEMBL:CHEMBL517938; ZINC:ZINC000014766825; SureChEMBL:SCHEMBL15006535; MolPort-035-706-482
Chemical structure download


BR-xanthone A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 396.44
Log P RDKit 4.56
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 23
Number of heavy atoms RDKit 29
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 10
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
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 5


BR-xanthone A
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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.541479


BR-xanthone A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.34
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes