IMPPAT Phytochemical information: 
Dillapionic acid

Dillapionic acid
Summary

SMILES: COc1c(cc2c(c1OC)OCO2)C(=O)O
InChI: InChI=1S/C10H10O6/c1-13-7-5(10(11)12)3-6-8(9(7)14-2)16-4-15-6/h3H,4H2,1-2H3,(H,11,12)
InChIKey: FRDRMVXVIUVAPV-UHFFFAOYSA-N
DeepSMILES: COcccccc6OC)))OCO5))))))C=O)O
Scaffold Graph/Node/Bond level: c1ccc2c(c1)OCO2
Scaffold Graph/Node level: C1CCC2OCOC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: cOC; c1cOCO1; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Benzoic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenolic acids (C6-C1)
NP Classifier Class: Simple phenolic acids
Synonymous chemical names:
dillapionic acid
Chemical structure download


Dillapionic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 226.18
Log P RDKit 1.13
Topological polar surface area (Å2) RDKit 74.22
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.3
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Dillapionic acid
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 0.83


Dillapionic 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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.83
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No