IMPPAT Phytochemical information: 
Phenethyl anthranilate
Phenethyl anthranilate
Summary

SMILES: O=C(c1ccccc1N)OCCc1ccccc1
InChI: InChI=1S/C15H15NO2/c16-14-9-5-4-8-13(14)15(17)18-11-10-12-6-2-1-3-7-12/h1-9H,10-11,16H2
InChIKey: PXWNBAGCFUDYBE-UHFFFAOYSA-N
DeepSMILES: O=Ccccccc6N)))))))OCCcccccc6
Scaffold Graph/Node/Bond level: O=C(OCCc1ccccc1)c1ccccc1
Scaffold Graph/Node level: OC(OCCC1CCCCC1)C1CCCCC1
Scaffold Graph level: CC(CCCC1CCCCC1)C1CCCCC1
Functional groups: cC(=O)OC; cN
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: Alkaloids
NP Classifier Superclass: Anthranilic acid alkaloids
NP Classifier Class: Anthranillic acid derivatives
Synonymous chemical names:
2-phenyl ethyl anthranilate, phenylethyl anthranilate, 2-phenylethyl anthranilate, phenylethylanthranilate
External chemical identifiers:
CID:CID_8615; ChEMBL:CHEMBL1488668; ZINC:ZINC000001693901; FDASRS:8HBK71OD81; SureChEMBL:SCHEMBL446803
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Phenethyl anthranilate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 241.29
Log P RDKit 2.67
Topological polar surface area (Å2) RDKit 52.32
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 3
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 13
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.13
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
Phenethyl anthranilate
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 0.66103
Phenethyl anthranilate
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 -4.82
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No