IMPPAT Phytochemical information: 
(-)-Bilobalide
(-)-Bilobalide
Summary

SMILES: O=C1O[C@@H]2[C@@]3(C1)C(=O)O[C@H]1[C@]3([C@](C2)(O)C(C)(C)C)[C@H](O)C(=O)O1
InChI: InChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8+,11-,13-,14+,15+/m0/s1
InChIKey: MOLPUWBMSBJXER-NRSGSQFTSA-N
DeepSMILES: O=CO[C@@H][C@@]C5)C=O)O[C@H][C@]5[C@]C8)O)CC)C)C)))[C@H]O)C=O)O5
Scaffold Graph/Node/Bond level: O=C1CC23CCC4OC(=O)CC42C(=O)OC3O1
Scaffold Graph/Node level: OC1CC23CCC4OC(O)CC42C(O)OC3O1
Scaffold Graph level: CC1CC2CC(C)C34CC(C)CC3CCC24C1
Functional groups: CC(=O)OC; O=C1CC2CC(=O)O[C@H]2O1; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
Synonymous chemical names:
bilobalide a
External chemical identifiers:
CID:CID_11875005; ZINC:ZINC000004046842; MolPort-002-519-347
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(-)-Bilobalide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 326.3
Log P RDKit -0.74
Topological polar surface area (Å2) RDKit 119.36
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 1
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 1
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
(-)-Bilobalide
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 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.558458
(-)-Bilobalide
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 High
Log Kp (Skin permeation, cm/s) SwissADME -8.48
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