IMPPAT Phytochemical information: 
Margosinolide
Margosinolide
Summary

SMILES: COC(=O)C[C@H]1[C@@]2(C)[C@H](O[C@H]3C2=C(C)[C@@H](C3)C2=CC(OC2=O)O)[C@H]2[C@@H]3[C@]1(C)C=CC(=O)[C@@]3(C)CO2
InChI: InChI=1S/C27H32O8/c1-12-13(14-9-19(30)35-24(14)31)8-15-20(12)27(4)16(10-18(29)32-5)25(2)7-6-17(28)26(3)11-33-21(22(25)26)23(27)34-15/h6-7,9,13,15-16,19,21-23,30H,8,10-11H2,1-5H3/t13-,15-,16-,19?,21-,22-,23-,25-,26-,27-/m1/s1
InChIKey: LUGYVZIXJLEPQF-CNNNJUAPSA-N
DeepSMILES: COC=O)C[C@H][C@@]C)[C@H]O[C@H]C5=CC)[C@@H]C5)C=CCOC5=O)))O)))))))))[C@H][C@@H][C@]6C)C=CC=O)[C@@]6C)CO9
Scaffold Graph/Node/Bond level: O=C1OCC=C1C1C=C2C(C1)OC1C2CC2C=CC(=O)C3COC1C23
Scaffold Graph/Node level: OC1CCC2CC3C4CC(C5CCOC5O)CC4OC3C3OCC1C23
Scaffold Graph level: CC1CCCC1C1CC2CC3C(CC4CCC(C)C5CCC3C45)C2C1
Functional groups: COC(C)=O; COC; CC(=C(C)C)C; CC1=CC(O)OC1=O; CC=CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthofurans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Limonoids
Synonymous chemical names:
margosinolide
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Margosinolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 484.55
Log P RDKit 2.26
Topological polar surface area (Å2) RDKit 108.36
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.37
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Margosinolide
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.480136
Margosinolide
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 High
Log Kp (Skin permeation, cm/s) SwissADME -8.46
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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