IMPPAT Phytochemical information: 
Macrophylloside
Macrophylloside
Summary

SMILES: OC[C@@H]1O[C@H](OC2O[C@H]3OC[C@]4(C2C([C@@H]3C(=O)OC)C=C4)O)[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C17H24O11/c1-24-13(22)8-6-2-3-17(23)5-25-14(8)27-15(9(6)17)28-16-12(21)11(20)10(19)7(4-18)26-16/h2-3,6-12,14-16,18-21,23H,4-5H2,1H3/t6?,7-,8+,9?,10-,11+,12-,14+,15?,16+,17+/m0/s1
InChIKey: YFEOPJWHUMIDGW-PZEGGROTSA-N
DeepSMILES: OC[C@@H]O[C@H]OCO[C@H]OC[C@]C7C[C@@H]7C=O)OC))))C=C5))))O))))))))[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=CC2CC3OCC1C2C(OC1CCCCO1)O3
Scaffold Graph/Node level: C1CCC(OC2OC3CC4CCC(CO3)C42)OC1
Scaffold Graph level: C1CCC(CC2CC3CCC4CCC(C3)C42)CC1
Functional groups: CO; CO[C@@H](C)OC(O[C@H](C)OC)C; COC(C)=O; CC=CC
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:
macrophylloside, Macrophylloside
External chemical identifiers:
CID:CID_101118343
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Macrophylloside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 404.37
Log P RDKit -3.16
Topological polar surface area (Å2) RDKit 164.37
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.65
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.82
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Macrophylloside
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.23718
Macrophylloside
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 -10.68
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 Yes