IMPPAT Phytochemical information: 
Bruceolide
Bruceolide
Summary

SMILES: COC(=O)[C@@]12OC[C@]34[C@H]2[C@@H](O)C(=O)O[C@@H]4C[C@@H]2[C@]([C@H]3[C@H]([C@@H]1O)O)(C)CC(=O)C(=C2C)O
InChI: InChI=1S/C21H26O10/c1-7-8-4-10-20-6-30-21(18(28)29-3,15(20)13(25)17(27)31-10)16(26)12(24)14(20)19(8,2)5-9(22)11(7)23/h8,10,12-16,23-26H,4-6H2,1-3H3/t8-,10+,12+,13+,14+,15+,16-,19-,20+,21-/m0/s1
InChIKey: YLWQKYSDNGHLAO-PWRINDRCSA-N
DeepSMILES: COC=O)[C@]OC[C@@][C@H]5[C@@H]O)C=O)O[C@@H]6C[C@@H][C@][C@H]%10[C@H][C@@H]%15O))O)))C)CC=O)C=C6C))O
Scaffold Graph/Node/Bond level: O=C1C=CC2CC3OC(=O)CC4C5CCC(C2C1)C34CO5
Scaffold Graph/Node level: OC1CCC2CC3OC(O)CC4C5CCC(C2C1)C34CO5
Scaffold Graph level: CC1CCC2CC3CC(C)CC4C5CCC(C2C1)C34CC5
Functional groups: COC(C)=O; COC; CO; COC(=O)C; CC(=O)C(O)=C(C)C
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
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Quassinoids
Synonymous chemical names:
bruceolide
External chemical identifiers:
CID:CID_99531; ChEMBL:CHEMBL140588; ChEBI:CHEBI:65529; ZINC:ZINC000027522274
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Bruceolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 438.43
Log P RDKit -1
Topological polar surface area (Å2) RDKit 159.82
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 4
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 5
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.76
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Bruceolide
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
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 0.37
Bruceolide
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 -9.77
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