IMPPAT Phytochemical information: 
Gardoside
Gardoside
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2C(=C)[C@H](C3)O)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C16H22O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4,6,8-13,15-21H,1-3H2,(H,22,23)/t6-,8+,9-,10-,11-,12+,13-,15+,16+/m1/s1
InChIKey: JSKCJJNYSGWZDU-RQJSCMEKSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]OC=C[C@@H][C@H]6C=C)[C@H]C5)O)))))C=O)O)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C=C1CCC2C=COC(OC3CCCCO3)C12
Scaffold Graph/Node level: CC1CCC2CCOC(OC3CCCCO3)C12
Scaffold Graph level: CC1CCC2CCCC(CC3CCCCC3)C12
Functional groups: CO; CO[C@@H](O[C@H]1CCC(C(=O)O)=CO1)C; C=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
gardoside, Gardoside
External chemical identifiers:
CID:CID_46173850; ChEMBL:CHEMBL3622810; ChEBI:CHEBI:80827; ZINC:ZINC000056874298
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Gardoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 374.34
Log P RDKit -2.32
Topological polar surface area (Å2) RDKit 166.14
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.56
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.69
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
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 3
Gardoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.294103
Gardoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
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 -10.34
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