IMPPAT Phytochemical information: 
Pyrethric acid

Pyrethric acid
Summary

SMILES: COC(=O)/C(=C/[C@@H]1[C@H](C1(C)C)C(=O)O)/C
InChI: InChI=1S/C11H16O4/c1-6(10(14)15-4)5-7-8(9(12)13)11(7,2)3/h5,7-8H,1-4H3,(H,12,13)/b6-5+/t7-,8+/m1/s1
InChIKey: UIWNHGWOYRFCSF-KTERXBQFSA-N
DeepSMILES: COC=O)/C=C/[C@@H][C@H]C3C)C))C=O)O)))))/C
Scaffold Graph/Node/Bond level: C1CC1
Scaffold Graph/Node level: C1CC1
Scaffold Graph level: C1CC1
Functional groups: COC(=O)/C(C)=C/C; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Monoterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Irregular monoterpenoids|Monocyclic monoterpenoids
Synonymous chemical names:
pyrethric-acid
External chemical identifiers:
CID:CID_12314791; ZINC:ZINC000033843871; SureChEMBL:SCHEMBL4418987
Chemical structure download


Pyrethric acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 212.25
Log P RDKit 1.46
Topological polar surface area (Å2) RDKit 63.6
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 15
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.64
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


Pyrethric acid
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 0.567937


Pyrethric acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -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 No
P-glycoprotein substrate SwissADME No