IMPPAT Phytochemical information: 
1-Hydroxy-2-(beta-D-glucosyloxy)-9,10-anthraquinone
1-Hydroxy-2-(beta-D-glucosyloxy)-9,10-anthraquinone
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2O)C(=O)c2c(C3=O)cccc2)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C20H18O9/c21-7-12-17(25)18(26)19(27)20(29-12)28-11-6-5-10-13(16(11)24)15(23)9-4-2-1-3-8(9)14(10)22/h1-6,12,17-21,24-27H,7H2/t12-,17-,18+,19-,20-/m1/s1
InChIKey: LPUCQUKLBVSNAF-UJXPUUNTSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6O))C=O)ccC6=O))cccc6)))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2cc(OC3CCCCO3)ccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2CC(OC3CCCCO3)CCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2CC(CC3CCCCC3)CCC12
Functional groups: CO; cO[C@@H](C)OC; cO; cC(=O)c
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:
alizarin glucoside
External chemical identifiers:
CID:CID_11988260; ChEMBL:CHEMBL1086418; ChEBI:CHEBI:17770; ZINC:ZINC000030725468; SureChEMBL:SCHEMBL3667069
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
1-Hydroxy-2-(beta-D-glucosyloxy)-9,10-anthraquinone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 402.36
Log P RDKit -0.65
Topological polar surface area (Å2) RDKit 153.75
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 9
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 14
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.3
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
1-Hydroxy-2-(beta-D-glucosyloxy)-9,10-anthraquinone
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 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 0.384296
1-Hydroxy-2-(beta-D-glucosyloxy)-9,10-anthraquinone
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 -8.12
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