IMPPAT Phytochemical information: 
Obacunone
Obacunone
Summary

SMILES: O=C1C=C[C@]2([C@H](C(O1)(C)C)CC(=O)[C@@]1([C@@H]2CC[C@@]2([C@]31O[C@@H]3C(=O)O[C@H]2c1ccoc1)C)C)C
InChI: InChI=1S/C26H30O7/c1-22(2)16-12-17(27)25(5)15(23(16,3)9-7-18(28)32-22)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)33-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3/t15-,16+,19+,20-,23-,24+,25+,26-/m1/s1
InChIKey: MAYJEFRPIKEYBL-OASIGRBWSA-N
DeepSMILES: O=CC=C[C@][C@H]CO7)C)C))CC=O)[C@@][C@@H]6CC[C@@][C@@]6O[C@@H]3C=O)O[C@H]7cccoc5)))))))))))C)))))C)))))C
Scaffold Graph/Node/Bond level: O=C1C=CC2C(CO1)CC(=O)C1C2CCC2C(c3ccoc3)OC(=O)C3OC321
Scaffold Graph/Node level: OC1CCC2C(CO1)CC(O)C1C2CCC2C(C3CCOC3)OC(O)C3OC231
Scaffold Graph level: CC1CCC2CC(C)C3C(CCC4C(C5CCCC5)CC(C)C5CC543)C2CC1
Functional groups: COC(=O)C=CC; CC(=O)C; C[C@]12CCOC(=O)[C@H]1O2; coc
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:
obacunone, Obacunone
External chemical identifiers:
CID:CID_119041; ChEMBL:CHEMBL404140; ChEBI:CHEBI:7713; ZINC:ZINC000004097789; SureChEMBL:SCHEMBL564187; MolPort-020-005-940
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Obacunone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 454.52
Log P RDKit 3.92
Topological polar surface area (Å2) RDKit 95.34
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
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
Obacunone
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 0
Ghose filter RDKit Passed
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 0.468681
Obacunone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.83
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
Obacunone
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000311032CASP3700
ENSP00000330237CASP9700
ENSP00000351273CASP8700
ENSP00000356438PTGS2824
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.