IMPPAT Phytochemical information: 
Rhein-8-glucoside calcium salt
Rhein-8-glucoside calcium salt
Summary

SMILES: OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1ccc(c2c1C(=O)c1cc(cc(c1C2=O)[O-])C(=O)O)[O-].[Ca+2]
InChI: InChI=1S/C21H18O11.Ca/c22-5-11-16(26)18(28)19(29)20(32-11)7-1-2-9(23)14-13(7)15(25)8-3-6(21(30)31)4-10(24)12(8)17(14)27;/h1-4,11,16,18-20,22-24,26,28-29H,5H2,(H,30,31);/q;+2/p-2/t11-,16-,18+,19-,20+;/m1./s1
InChIKey: XXVBCAMVOFYHJP-WJGQHNSASA-L
DeepSMILES: OC[C@H]O[C@H][C@@H][C@H][C@@H]6O))O))O))cccccc6C=O)cccccc6C%10=O)))[O-])))C=O)O))))))))[O-].[Ca+2]
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2c1cccc2C1CCCCO1
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2C(C3CCCCO3)CCCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2C(C3CCCCC3)CCCC12
Functional groups: CO; [Ca+2]; COC; cC(=O)c; c[O-]; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Anthracenes
ClassyFire Subclass: Anthracenecarboxylic acids and derivatives
Synonymous chemical names:
gluco-rhein, glucorhein
External chemical identifiers:
CID:CID_54676854; ChEBI:CHEBI:172683
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Rhein-8-glucoside calcium salt
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 484.43
Log P RDKit -2.56
Topological polar surface area (Å2) RDKit 207.71
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 12
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 15
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.29
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
Rhein-8-glucoside calcium salt
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 2
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 0.24
Rhein-8-glucoside calcium salt
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
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 -9.42
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