IMPPAT Phytochemical information: 
Toonacilin
Toonacilin
Summary

SMILES: COC(=O)C[C@@H]1[C@](C)(C=CC(=O)C1(C)C)[C@H]1[C@H](OC(=O)C)[C@H](OC(=O)C)[C@@]2([C@]3(C1=C)O[C@@H]3C[C@H]2c1cocc1)C
InChI: InChI=1S/C31H38O9/c1-16-25(29(6)11-9-22(34)28(4,5)21(29)14-24(35)36-8)26(38-17(2)32)27(39-18(3)33)30(7)20(19-10-12-37-15-19)13-23-31(16,30)40-23/h9-12,15,20-21,23,25-27H,1,13-14H2,2-8H3/t20-,21-,23+,25+,26-,27-,29-,30+,31+/m0/s1
InChIKey: RRBQYKQIAKFGIS-AMVRVENBSA-N
DeepSMILES: COC=O)C[C@@H][C@]C)C=CC=O)C6C)C)))))[C@H][C@H]OC=O)C)))[C@H]OC=O)C)))[C@@][C@]C6=C))O[C@@H]3C[C@H]6ccocc5))))))))))C
Scaffold Graph/Node/Bond level: C=C1C(C2C=CC(=O)CC2)CCC2C(c3ccoc3)CC3OC132
Scaffold Graph/Node level: CC1C(C2CCC(O)CC2)CCC2C(C3CCOC3)CC3OC312
Scaffold Graph level: CC1CCC(C2CCC3C(C4CCCC4)CC4CC43C2C)CC1
Functional groups: COC(C)=O; CC(=O)C=CC; CC(=O)OC; C=C(C)[C@@]1(C)O[C@@H]1C; 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:
toonacilin
External chemical identifiers:
CID:CID_181814; ChEBI:CHEBI:9632; ZINC:ZINC000004097792
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Toonacilin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 554.64
Log P RDKit 4.31
Topological polar surface area (Å2) RDKit 121.64
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 31
Number of heavy atoms RDKit 40
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 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.61
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Toonacilin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
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 0.219084
Toonacilin
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 -7.52
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