IMPPAT Phytochemical information: 
6'-O-Glucosylaucubin
6'-O-Glucosylaucubin
Summary

SMILES: OCC1=C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O)O
InChI: InChI=1S/C21H32O14/c22-4-7-3-9(24)8-1-2-31-19(12(7)8)35-21-18(30)16(28)14(26)11(34-21)6-32-20-17(29)15(27)13(25)10(5-23)33-20/h1-3,8-30H,4-6H2/t8-,9+,10+,11+,12+,13+,14+,15-,16-,17+,18+,19-,20+,21-/m0/s1
InChIKey: NOVFAHFRCMKDBE-HIKVWFBOSA-N
DeepSMILES: OCC=C[C@H][C@H][C@@H]5[C@@H]OC=C6)))O[C@@H]O[C@H]CO[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O)))))))[C@H][C@@H][C@H]6O))O))O)))))))))O
Scaffold Graph/Node/Bond level: C1=CC2C(C=COC2OC2CCCC(COC3CCCCO3)O2)C1
Scaffold Graph/Node level: C1CCC(OCC2CCCC(OC3OCCC4CCCC43)O2)OC1
Scaffold Graph level: C1CCC(CCC2CCCC(CC3CCCC4CCCC43)C2)CC1
Functional groups: CO; CC(=CC)C; CO[C@@H](O[C@H]1CCC=CO1)C; CO[C@@H](C)OC
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: Iridoids monoterpenoids
Synonymous chemical names:
6'-0-beta-glucosylaucubin
External chemical identifiers:
CID:CID_101085816; ZINC:ZINC000085646216
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
6'-O-Glucosylaucubin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 508.47
Log P RDKit -4.98
Topological polar surface area (Å2) RDKit 228.22
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 14
Stereochemical complexity RDKit 0.67
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 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
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 4
6'-O-Glucosylaucubin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 2
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.15
6'-O-Glucosylaucubin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -13.07
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