IMPPAT Phytochemical information: 
Rubianin
Rubianin
Summary

SMILES: OC[C@H]1OC([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)cc2c(c1O)C(=O)c1c(C2=O)cccc1
InChI: InChI=1S/C20H18O9/c21-6-11-16(25)18(27)19(28)20(29-11)13-10(22)5-9-12(17(13)26)15(24)8-4-2-1-3-7(8)14(9)23/h1-5,11,16,18-22,25-28H,6H2/t11-,16-,18+,19-,20?/m1/s1
InChIKey: WTHXGIAKMIQVNJ-YFKYUTKVSA-N
DeepSMILES: OC[C@H]OC[C@@H][C@H][C@@H]6O))O))O))ccO)cccc6O))C=O)ccC6=O))cccc6
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2cc(C3CCCCO3)ccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2CC(C3CCCCO3)CCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2CC(C3CCCCC3)CCC12
Functional groups: CO; COC; 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:
rubianin
External chemical identifiers:
CID:CID_90477758
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Rubianin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 402.36
Log P RDKit -0.61
Topological polar surface area (Å2) RDKit 164.75
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 6
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 2
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
Rubianin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
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 0.33
Rubianin
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 -8.58
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 No