IMPPAT Phytochemical information: 
9H-Xanthen-9-one, 1,8-dihydroxy-5-(beta-D-glucopyranosyloxy)-3-methoxy-
9H-Xanthen-9-one, 1,8-dihydroxy-5-(beta-D-glucopyranosyloxy)-3-methoxy-
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc(c3c2oc2cc(OC)cc(c2c3=O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C20H20O11/c1-28-7-4-9(23)13-11(5-7)29-19-10(3-2-8(22)14(19)16(13)25)30-20-18(27)17(26)15(24)12(6-21)31-20/h2-5,12,15,17-18,20-24,26-27H,6H2,1H3/t12-,15-,17+,18-,20-/m1/s1
InChIKey: TYODMTITEULVMF-DIKOWXHZSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6occcOC))ccc6c%10=O)))O)))))))))O))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1c2ccccc2oc2c(OC3CCCCO3)cccc12
Scaffold Graph/Node level: OC1C2CCCCC2OC2C(OC3CCCCO3)CCCC12
Scaffold Graph level: CC1C2CCCCC2CC2C(CC3CCCCC3)CCCC12
Functional groups: CO; cO[C@@H](C)OC; 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:
Isoswertianolin, isoswertianolin
External chemical identifiers:
CID:CID_5745358
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
9H-Xanthen-9-one, 1,8-dihydroxy-5-(beta-D-glucopyranosyloxy)-3-methoxy-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 436.37
Log P RDKit -0.46
Topological polar surface area (Å2) RDKit 179.28
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
9H-Xanthen-9-one, 1,8-dihydroxy-5-(beta-D-glucopyranosyloxy)-3-methoxy-
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.29
9H-Xanthen-9-one, 1,8-dihydroxy-5-(beta-D-glucopyranosyloxy)-3-methoxy-
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.52
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 Yes