IMPPAT Phytochemical information: 
Aurantiamide benzoate
Aurantiamide benzoate
Summary

SMILES: O=C([C@@H](NC(=O)c1ccccc1)Cc1ccccc1)N[C@@H](Cc1ccccc1)COC(=O)c1ccccc1
InChI: InChI=1S/C32H30N2O4/c35-30(26-17-9-3-10-18-26)34-29(22-25-15-7-2-8-16-25)31(36)33-28(21-24-13-5-1-6-14-24)23-38-32(37)27-19-11-4-12-20-27/h1-20,28-29H,21-23H2,(H,33,36)(H,34,35)/t28-,29-/m0/s1
InChIKey: WJJGUIYRXBJSMQ-VMPREFPWSA-N
DeepSMILES: O=C[C@@H]NC=O)cccccc6))))))))Ccccccc6))))))))N[C@@H]Ccccccc6)))))))COC=O)cccccc6
Scaffold Graph/Node/Bond level: O=C(NC(Cc1ccccc1)C(=O)NC(COC(=O)c1ccccc1)Cc1ccccc1)c1ccccc1
Scaffold Graph/Node level: OC(NC(CC1CCCCC1)C(O)NC(COC(O)C1CCCCC1)CC1CCCCC1)C1CCCCC1
Scaffold Graph level: CC(CCC(CC1CCCCC1)CC(C)C(CC1CCCCC1)CC(C)C1CCCCC1)C1CCCCC1
Functional groups: CNC(C)=O; cC(=O)NC; cC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
Synonymous chemical names:
aurantiamide benzoate
External chemical identifiers:
CID:CID_102153907; ZINC:ZINC000013374328
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Aurantiamide benzoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 506.6
Log P RDKit 4.61
Topological polar surface area (Å2) RDKit 84.5
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 27
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.16
Number of rotatable bonds RDKit 12
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 4
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 4
Aurantiamide benzoate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.291078
Aurantiamide benzoate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.05
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes