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(=C\C)/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=C\C))/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: CO[C@@](O)(C)C; COC(C)=O; C=C1CCOC1=O; C/C=C(/C)C(=O)OC; CO
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: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 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.35
Ineupatolide
ADME 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
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 Yes
P-glycoprotein substrate SwissADME Yes