IMPPAT Phytochemical information: 
Taraxacoside

Taraxacoside
Summary

SMILES: OCC1OC(OC2COC(=O)C2)C(C(C1OC(=O)Cc1ccc(cc1)O)O)O
InChI: InChI=1S/C18H22O10/c19-7-12-17(28-14(22)5-9-1-3-10(20)4-2-9)15(23)16(24)18(27-12)26-11-6-13(21)25-8-11/h1-4,11-12,15-20,23-24H,5-8H2
InChIKey: ZNBBYALXAQXHJE-UHFFFAOYSA-N
DeepSMILES: OCCOCOCCOC=O)C5))))))CCC6OC=O)Ccccccc6))O)))))))))O))O
Scaffold Graph/Node/Bond level: O=C1CC(OC2CCC(OC(=O)Cc3ccccc3)CO2)CO1
Scaffold Graph/Node level: OC1CC(OC2CCC(OC(O)CC3CCCCC3)CO2)CO1
Scaffold Graph level: CC(CC1CCCCC1)CC1CCC(CC2CCC(C)C2)CC1
Functional groups: CO; COC(OC)C; COC(=O)C; COC(C)=O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
taraxacoside
External chemical identifiers:
CID:CID_131750952; ChEBI:CHEBI:168895
Chemical structure download


Taraxacoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 398.36
Log P RDKit -1.38
Topological polar surface area (Å2) RDKit 151.98
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.56
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 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3


Taraxacoside
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 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.42


Taraxacoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.53
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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