IMPPAT Phytochemical information: 
beta-D-Glucopyranoside, (2S)-5-methyl-2-(1-methylethenyl)-4-hexenyl 6-O-alpha-L-arabinopyranosyl-
beta-D-Glucopyranoside, (2S)-5-methyl-2-(1-methylethenyl)-4-hexenyl 6-O-alpha-L-arabinopyranosyl-
Summary

SMILES: CC(=CCC(C(=C)C)CO[C@H]1O[C@H](CO[C@@H]2OC[C@@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
InChI: InChI=1S/C21H36O10/c1-10(2)5-6-12(11(3)4)7-28-21-19(27)17(25)16(24)14(31-21)9-30-20-18(26)15(23)13(22)8-29-20/h5,12-27H,3,6-9H2,1-2,4H3/t12?,13-,14+,15-,16+,17-,18+,19-,20-,21-/m0/s1
InChIKey: XOSSHORSTHFGFX-OMHAHRJWSA-N
DeepSMILES: CC=CCCC=C)C))CO[C@H]O[C@H]CO[C@@H]OC[C@@H][C@@H][C@H]6O))O))O)))))))[C@H][C@@H][C@@H]6O))O))O))))))))))C
Scaffold Graph/Node/Bond level: C1CCC(COC2CCCCO2)OC1
Scaffold Graph/Node level: C1CCC(COC2CCCCO2)OC1
Scaffold Graph level: C1CCC(CCC2CCCCC2)CC1
Functional groups: CC=C(C)C; C=C(C)C; CO[C@H](C)OC; CO[C@@H](C)OC; CO
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: Acyclic monoterpenoids
Synonymous chemical names:
kenposide b
External chemical identifiers:
CID:CID_192589
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
beta-D-Glucopyranoside, (2S)-5-methyl-2-(1-methylethenyl)-4-hexenyl 6-O-alpha-L-arabinopyranosyl-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 448.51
Log P RDKit -1.19
Topological polar surface area (Å2) RDKit 158.3
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.48
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.81
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
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 2
beta-D-Glucopyranoside, (2S)-5-methyl-2-(1-methylethenyl)-4-hexenyl 6-O-alpha-L-arabinopyranosyl-
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 0.237037
beta-D-Glucopyranoside, (2S)-5-methyl-2-(1-methylethenyl)-4-hexenyl 6-O-alpha-L-arabinopyranosyl-
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 -9.50
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