IMPPAT Phytochemical information: 
Z-harpagoside
Z-harpagoside
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@]3([C@H]2[C@@](C)(OC(=O)/C=C\c2ccccc2)C[C@H]3O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C24H30O11/c1-23(35-16(27)8-7-13-5-3-2-4-6-13)11-15(26)24(31)9-10-32-22(20(23)24)34-21-19(30)18(29)17(28)14(12-25)33-21/h2-10,14-15,17-22,25-26,28-31H,11-12H2,1H3/b8-7-/t14-,15-,17-,18+,19-,20-,21+,22+,23+,24-/m1/s1
InChIKey: KVRQGMOSZKPBNS-BCIAEHMOSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]OC=C[C@@][C@H]6[C@@]C)OC=O)/C=C\cccccc6))))))))))C[C@H]5O)))))O)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCC2C=COC(OC3CCCCO3)C21
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCC2CCOC(OC3CCCCO3)C21
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCC2CCCC(CC3CCCCC3)C21
Functional groups: CO; CO[C@@H](O[C@H]1CCC=CO1)C; c/C=C\C(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
harpagoside
External chemical identifiers:
CID:CID_13889700; ChEMBL:CHEMBL464888; ZINC:ZINC000044388285; MolPort-001-742-813
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Z-harpagoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 494.49
Log P RDKit -1.2
Topological polar surface area (Å2) RDKit 175.37
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.42
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.54
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Z-harpagoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
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 0.21
Z-harpagoside
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 -9.75
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