IMPPAT Phytochemical information: 
Amygdaloside
Amygdaloside
Summary

SMILES: OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(c3ccccc3)C#N)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C20H27NO11/c21-6-10(9-4-2-1-3-5-9)30-20-18(28)16(26)14(24)12(32-20)8-29-19-17(27)15(25)13(23)11(7-22)31-19/h1-5,10-20,22-28H,7-8H2/t10?,11-,12-,13-,14-,15+,16+,17-,18-,19-,20-/m1/s1
InChIKey: XUCIJNAGGSZNQT-SWRVSKMJSA-N
DeepSMILES: OC[C@H]O[C@@H]OC[C@H]O[C@@H]OCcccccc6))))))C#N))))[C@@H][C@H][C@@H]6O))O))O)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1ccc(COC2CCCC(COC3CCCCO3)O2)cc1
Scaffold Graph/Node level: C1CCC(COC2CCCC(COC3CCCCO3)O2)CC1
Scaffold Graph level: C1CCC(CCC2CCCC(CCC3CCCCC3)C2)CC1
Functional groups: CO; CO[C@@H](C)OC; CC#N
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
amygdalin
External chemical identifiers:
CID:CID_34751; ChEMBL:CHEMBL515712; ChEBI:CHEBI:27613; SureChEMBL:SCHEMBL131407; MolPort-002-911-378
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Amygdaloside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 457.43
Log P RDKit -3.11
Topological polar surface area (Å2) RDKit 202.32
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.55
Number of sp hybridized carbon atoms RDKit 1
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.68
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
Amygdaloside
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
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 0.217518
Amygdaloside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -11.01
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 No