IMPPAT Phytochemical information: 
Vitexilactone

Vitexilactone
Summary

SMILES: CC(=O)O[C@@H]1C[C@@H](C)[C@]([C@@]2([C@@H]1C(C)(C)CCC2)C)(O)CCC1=CC(=O)OC1
InChI: InChI=1S/C22H34O5/c1-14-11-17(27-15(2)23)19-20(3,4)8-6-9-21(19,5)22(14,25)10-7-16-12-18(24)26-13-16/h12,14,17,19,25H,6-11,13H2,1-5H3/t14-,17-,19+,21+,22-/m1/s1
InChIKey: FBWWXAGANVJTLU-HEXLTJKYSA-N
DeepSMILES: CC=O)O[C@@H]C[C@@H]C)[C@][C@@][C@@H]6CC)C)CCC6)))))C))O)CCC=CC=O)OC5
Scaffold Graph/Node/Bond level: O=C1C=C(CCC2CCCC3CCCCC32)CO1
Scaffold Graph/Node level: OC1CC(CCC2CCCC3CCCCC32)CO1
Scaffold Graph level: CC1CCC(CCC2CCCC3CCCCC32)C1
Functional groups: CC(=O)OC; CO; CC1=CC(=O)OC1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Labdane diterpenoids
Synonymous chemical names:
vitexilactone
External chemical identifiers:
CID:CID_21636178; ChEMBL:CHEMBL517619; ChEBI:CHEBI:91267; ZINC:ZINC000031157139; FDASRS:8HP9QLE96R; SureChEMBL:SCHEMBL4931755; MolPort-035-705-907
Chemical structure download


Vitexilactone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 378.51
Log P RDKit 3.79
Topological polar surface area (Å2) RDKit 72.83
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.82
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
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 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Vitexilactone
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.75375


Vitexilactone
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.93
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No