IMPPAT Phytochemical information: 
1,8-dihydroxy-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]-10H-anthracen-9-one
1,8-dihydroxy-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]-10H-anthracen-9-one
Summary

SMILES: OCC1OC(C(C(C1O)O)O)C1c2cc(COC3OC(C)C(C(C3O)O)O)cc(c2C(=O)c2c1cccc2O)O
InChI: InChI=1S/C27H32O13/c1-9-19(31)22(34)25(37)27(39-9)38-8-10-5-12-16(26-24(36)23(35)20(32)15(7-28)40-26)11-3-2-4-13(29)17(11)21(33)18(12)14(30)6-10/h2-6,9,15-16,19-20,22-32,34-37H,7-8H2,1H3
InChIKey: BUPDVJFRVYWYEV-UHFFFAOYSA-N
DeepSMILES: OCCOCCCC6O))O))O))CcccCOCOCC)CCC6O))O))O)))))))ccc6C=O)cc%10cccc6O)))))))))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(C2CCCCO2)c2cc(COC3CCCCO3)ccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(C2CCCCO2)C2CC(COC3CCCCO3)CCC12
Scaffold Graph level: CC1C2CCCCC2C(C2CCCCC2)C2CC(CCC3CCCCC3)CCC12
Functional groups: CO; COC; cO; COC(C)OC; cC(=O)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Anthracenes
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Polycyclic aromatic polyketides
NP Classifier Class: Anthraquinones and anthrones
Synonymous chemical names:
aloinoside b
External chemical identifiers:
CID:CID_313324
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
1,8-dihydroxy-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]-10H-anthracen-9-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 564.54
Log P RDKit -2.04
Topological polar surface area (Å2) RDKit 226.83
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
1,8-dihydroxy-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]-10H-anthracen-9-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
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 0.190984
1,8-dihydroxy-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]-10H-anthracen-9-one
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 -10.61
Number of PAINS structural alerts SwissADME 0
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