IMPPAT Phytochemical information: 
23-Hydroxytoonacilide
23-Hydroxytoonacilide
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]2C1=CC(OC1=O)O)C
InChI: InChI=1S/C31H38O11/c1-14-24(29(6)10-9-20(34)28(4,5)19(29)13-22(35)38-8)25(39-15(2)32)26(40-16(3)33)30(7)18(12-21-31(14,30)42-21)17-11-23(36)41-27(17)37/h9-11,18-19,21,23-26,36H,1,12-13H2,2-8H3/t18-,19-,21+,23?,24+,25+,26-,29-,30+,31+/m0/s1
InChIKey: JMIQCHPADBJCET-VKUOMARPSA-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]6C=CCOC5=O)))O)))))))))C
Scaffold Graph/Node/Bond level: C=C1C(C2C=CC(=O)CC2)CCC2C(C3=CCOC3=O)CC3OC132
Scaffold Graph/Node level: CC1C(C2CCC(O)CC2)CCC2C(C3CCOC3O)CC3OC312
Scaffold Graph level: CC1CCC(C2CCC3C(C4CCCC4C)CC4CC43C2C)CC1
Functional groups: COC(C)=O; CC(=O)C=CC; CC(=O)OC; C=C(C)[C@@]1(C)O[C@@H]1C; CC1=CC(O)OC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Tetracarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Limonoids
Synonymous chemical names:
23-hydroxytoonacilide
External chemical identifiers:
CID:CID_5318363; ChEMBL:CHEMBL2035089
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
23-Hydroxytoonacilide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 586.63
Log P RDKit 2.35
Topological polar surface area (Å2) RDKit 155.03
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 31
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.32
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 20
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
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
23-Hydroxytoonacilide
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 Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.211018
23-Hydroxytoonacilide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.65
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 No