IMPPAT Phytochemical information: 
Methylenedioxybenzoyl ethyl PABA

Methylenedioxybenzoyl ethyl PABA
Summary

SMILES: CCOC(=O)c1ccc(cc1)NC(=O)c1ccc2c(c1)OCO2
InChI: InChI=1S/C17H15NO5/c1-2-21-17(20)11-3-6-13(7-4-11)18-16(19)12-5-8-14-15(9-12)23-10-22-14/h3-9H,2,10H2,1H3,(H,18,19)
InChIKey: MNAPLMLDXHLQRT-UHFFFAOYSA-N
DeepSMILES: CCOC=O)cccccc6))NC=O)cccccc6)OCO5
Scaffold Graph/Node/Bond level: O=C(Nc1ccccc1)c1ccc2c(c1)OCO2
Scaffold Graph/Node level: OC(NC1CCCCC1)C1CCC2OCOC2C1
Scaffold Graph level: CC(CC1CCCCC1)C1CCC2CCCC2C1
Functional groups: cC(=O)OC; cNC(c)=O; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Anilides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
formetin
External chemical identifiers:
CID:CID_785868; ChEMBL:CHEMBL1504889; ZINC:ZINC000000282828; FDASRS:5U05P81M8W; MolPort-001-491-627
Chemical structure download


Methylenedioxybenzoyl ethyl PABA
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 313.31
Log P RDKit 2.84
Topological polar surface area (Å2) RDKit 73.86
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
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 14
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.18
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Methylenedioxybenzoyl ethyl PABA
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 0.878633


Methylenedioxybenzoyl ethyl PABA
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 -5.60
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No