IMPPAT Phytochemical information: 
Ineupatolide
Ineupatolide
Summary

SMILES: CC[C@H](C(=O)O[C@H]1[C@@H]2OC(=O)C(=C)[C@H]2[C@H](OC(=O)/C(=CC)/C)[C@@]2(O[C@H](C[C@@]1(C)O)C[C@@H]2C)O)C
InChI: InChI=1S/C25H36O9/c1-8-12(3)21(26)32-19-17-15(6)23(28)31-18(17)20(33-22(27)13(4)9-2)24(7,29)11-16-10-14(5)25(19,30)34-16/h8,13-14,16-20,29-30H,6,9-11H2,1-5,7H3/b12-8-/t13-,14+,16+,17-,18-,19+,20+,24-,25-/m1/s1
InChIKey: LYSXXZROYWKWEQ-ZQZQXELWSA-N
DeepSMILES: CC[C@H]C=O)O[C@H][C@@H]OC=O)C=C)[C@H]5[C@H]OC=O)/C=CC))/C))))[C@@]O[C@H]C[C@@]%12C)O)))C[C@@H]5C)))))O)))))))))))C
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2CCCC3CCC(CC12)O3
Scaffold Graph/Node level: CC1C(O)OC2CCCC3CCC(CC21)O3
Scaffold Graph level: CC1CC2CCCC3CCC(C3)CC2C1C
Functional groups: C/C=C(/C)C(=O)OC; C=C1CCOC1=O; CO; COC(C)=O; CO[C@](C)(C)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Tricarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Germacrane sesquiterpenoids
Synonymous chemical names:
ineupatolide
External chemical identifiers:
CID:21603602; ZINC:ZINC000095911291
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ineupatolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 480.55
Log P RDKit 2.19
Topological polar surface area (Å2) RDKit 128.59
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.36
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.72
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Ineupatolide
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 0.3455
Ineupatolide
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.13
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 2.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes