IMPPAT Phytochemical information: 
Paniculide-a

Paniculide-a
Summary

SMILES: CC(=CCCC1=C2C(OC1=O)CC1(C(C2O)O1)C)C
InChI: InChI=1S/C15H20O4/c1-8(2)5-4-6-9-11-10(18-14(9)17)7-15(3)13(19-15)12(11)16/h5,10,12-13,16H,4,6-7H2,1-3H3
InChIKey: TVGBYMMWMJGHSY-UHFFFAOYSA-N
DeepSMILES: CC=CCCC=CCOC5=O)))CCCC6O))O3))C)))))))))C
Scaffold Graph/Node/Bond level: O=C1C=C2CC3OC3CC2O1
Scaffold Graph/Node level: OC1CC2CC3OC3CC2O1
Scaffold Graph level: CC1CC2CC3CC3CC2C1
Functional groups: CC=C(C)C; CC1=C(C)C(=O)OC1; CC1OC1(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Oxepanes
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Bisabolane sesquiterpenoids
Synonymous chemical names:
paniculide-a
Chemical structure download


Paniculide-a
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 264.32
Log P RDKit 1.88
Topological polar surface area (Å2) RDKit 59.06
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
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 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Paniculide-a
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.48


Paniculide-a
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.02
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 No