IMPPAT Phytochemical information: 
6,8-dihydroxy-3-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6-tetrah ydropyran-2-yloxy)]anthracene-9,10-dione
6,8-dihydroxy-3-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6-tetrah ydropyran-2-yloxy)]anthracene-9,10-dione
Summary

SMILES: OCC1OC(Oc2cc(C)cc3c2C(=O)c2c(C3=O)cc(cc2O)O)C(C(C1O)O)O
InChI: InChI=1S/C21H20O10/c1-7-2-9-15(18(27)14-10(16(9)25)4-8(23)5-11(14)24)12(3-7)30-21-20(29)19(28)17(26)13(6-22)31-21/h2-5,13,17,19-24,26,28-29H,6H2,1H3
InChIKey: ZXXFEBMBNPRRSI-UHFFFAOYSA-N
DeepSMILES: OCCOCOcccC)ccc6C=O)ccC6=O))cccc6O)))O)))))))))))))CCC6O))O))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2c(OC3CCCCO3)cccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2C(OC3CCCCO3)CCCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2C(CC3CCCCC3)CCCC12
Functional groups: CO; cOC(C)OC; cC(=O)c; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Anthracenes
ClassyFire Subclass: Anthraquinones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Polycyclic aromatic polyketides
NP Classifier Class: Anthraquinones and anthrones
Synonymous chemical names:
physcion-1-o-β-d-glucopyranoside
External chemical identifiers:
CID:CID_13084799; MolPort-009-753-044
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
6,8-dihydroxy-3-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6-tetrah ydropyran-2-yloxy)]anthracene-9,10-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 432.38
Log P RDKit -0.64
Topological polar surface area (Å2) RDKit 173.98
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
6,8-dihydroxy-3-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6-tetrah ydropyran-2-yloxy)]anthracene-9,10-dione
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.312347
6,8-dihydroxy-3-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6-tetrah ydropyran-2-yloxy)]anthracene-9,10-dione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -8.29
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
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