IMPPAT Phytochemical information: 
Compositolide
Compositolide
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@@H](OC(=O)/C(=C/C)/C)C[C@H]([C@@]3(C)CO2)OC(=O)C
InChI: InChI=1S/C34H44O11/c1-9-15(2)30(38)44-23-13-22(42-17(4)35)32(5)14-41-27-28(32)33(23,6)21(12-24(36)40-8)34(7)26-16(3)18(10-20(26)43-29(27)34)19-11-25(37)45-31(19)39/h9,11,18,20-23,25,27-29,37H,10,12-14H2,1-8H3/b15-9+/t18-,20-,21-,22-,23+,25?,27-,28+,29-,32-,33+,34-/m1/s1
InChIKey: FVEVYGNIVRCALL-HTFNIQLJSA-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@@H]OC=O)/C=C/C))/C))))C[C@H][C@@]6C)CO9)))OC=O)C
Scaffold Graph/Node/Bond level: O=C1OCC=C1C1C=C2C(C1)OC1C2CC2CCCC3COC1C32
Scaffold Graph/Node level: OC1OCCC1C1CC2OC3C(CC4CCCC5COC3C54)C2C1
Scaffold Graph level: CC1CCCC1C1CC2CC3C(CC4CCCC5CCC3C54)C2C1
Functional groups: COC(C)=O; COC; CC(=C(C)C)C; CC1=CC(O)OC1=O; C/C=C(\C)C(=O)OC; CC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Limonoids
Synonymous chemical names:
compositolide, salannolide
External chemical identifiers:
CID:CID_76309326; ChEMBL:CHEMBL2288872
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Compositolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 628.72
Log P RDKit 3.33
Topological polar surface area (Å2) RDKit 143.89
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 45
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 24
Shape complexity RDKit 0.71
Number of rotatable bonds RDKit 9
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 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Compositolide
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.200211
Compositolide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.27
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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