IMPPAT Phytochemical information: 
Vestolide

Vestolide
Summary

SMILES: OC1CC(C)(O)C2C(C3C1C(=C)C(=O)O3)C(CC2)(C)O
InChI: InChI=1S/C15H22O5/c1-7-10-9(16)6-15(3,19)8-4-5-14(2,18)11(8)12(10)20-13(7)17/h8-12,16,18-19H,1,4-6H2,2-3H3
InChIKey: POOWACKONHGRLI-UHFFFAOYSA-N
DeepSMILES: OCCCC)O)CCCC7C=C)C=O)O5)))))CCC5))C)O
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2C1CCCC1CCCC12
Scaffold Graph/Node level: CC1C(O)OC2C3CCCC3CCCC12
Scaffold Graph level: CC1CC2C3CCCC3CCCC2C1C
Functional groups: CO; C=C1CCOC1=O
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: Sesquiterpenoids
NP Classifier Class: Guaiane sesquiterpenoids
Synonymous chemical names:
vestolide
External chemical identifiers:
CID:CID_90477642
Chemical structure download


Vestolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 282.34
Log P RDKit 0.38
Topological polar surface area (Å2) RDKit 86.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.47
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 0
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 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Vestolide
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.441447


Vestolide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.84
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 No
P-glycoprotein substrate SwissADME Yes