IMPPAT Phytochemical information: 
Plumerubroside
Plumerubroside
Summary

SMILES: OCC1O[C@@H](Oc2cc(OC)cc3c2C[C@H](O)[C@H](O3)c2cc(OC)c(c(c2)OC)O)C([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C24H30O12/c1-31-11-6-14-12(15(7-11)35-24-22(30)21(29)20(28)18(9-25)36-24)8-13(26)23(34-14)10-4-16(32-2)19(27)17(5-10)33-3/h4-7,13,18,20-30H,8-9H2,1-3H3/t13-,18?,20+,21-,22?,23+,24+/m0/s1
InChIKey: IBKHAIJVZGYPDV-AEHBIEOASA-N
DeepSMILES: OCCO[C@@H]OcccOC))ccc6C[C@H]O)[C@H]O6)cccOC))ccc6)OC)))O)))))))))))))))C[C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1ccc(C2CCc3c(OC4CCCCO4)cccc3O2)cc1
Scaffold Graph/Node level: C1CCC(C2CCC3C(OC4CCCCO4)CCCC3O2)CC1
Scaffold Graph level: C1CCC(CC2CCCC3CC(C4CCCCC4)CCC23)CC1
Functional groups: CO; cO[C@@H](C)OC; cOC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavan-3-ols
Synonymous chemical names:
Plumerubroside, plumerubroside, (2r,3s)-3,4'-dihydroxy-7-3',5'-trimethoxyflavan-5-o-β-d-glucopyranoside (plumerubroside)
External chemical identifiers:
CID:CID_44257126
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Plumerubroside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 510.49
Log P RDKit -0.37
Topological polar surface area (Å2) RDKit 176.76
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
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
Plumerubroside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
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 0.29
Plumerubroside
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 -9.24
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