IMPPAT Phytochemical information: 
Khelloside

Khelloside
Summary

SMILES: OC[C@H]1O[C@@H](OCc2cc(=O)c3c(o2)cc2c(c3OC)cco2)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C19H20O10/c1-25-18-9-2-3-26-11(9)5-12-14(18)10(21)4-8(28-12)7-27-19-17(24)16(23)15(22)13(6-20)29-19/h2-5,13,15-17,19-20,22-24H,6-7H2,1H3/t13-,15-,16+,17-,19-/m1/s1
InChIKey: SJRACCTZSAUMGO-WIMVFMHDSA-N
DeepSMILES: OC[C@H]O[C@@H]OCccc=O)cco6)cccc6OC)))cco5)))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1cc(COC2CCCCO2)oc2cc3occc3cc12
Scaffold Graph/Node level: OC1CC(COC2CCCCO2)OC2CC3OCCC3CC12
Scaffold Graph level: CC1CC(CCC2CCCCC2)CC2CC3CCCC3CC12
Functional groups: CO; CO[C@@H](C)OC; c=O; coc; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Chromanes
NP Classifier Class: Chromones
Synonymous chemical names:
khellinin, khellol glucoside, Khellinin
External chemical identifiers:
CID:CID_441966; ChEMBL:CHEMBL3989710; ChEBI:CHEBI:6134; ZINC:ZINC000004097843; FDASRS:ZX4FRZ5WJP; SureChEMBL:SCHEMBL2110571; MolPort-001-740-502
Chemical structure download


Khelloside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 408.36
Log P RDKit -0.14
Topological polar surface area (Å2) RDKit 151.96
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Khelloside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
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 0.448898


Khelloside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -9.18
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