IMPPAT Phytochemical information: 
Aurantiamide
Aurantiamide
Summary

SMILES: OC[C@@H](NC(=O)[C@@H](NC(=O)c1ccccc1)Cc1ccccc1)Cc1ccccc1
InChI: InChI=1S/C25H26N2O3/c28-18-22(16-19-10-4-1-5-11-19)26-25(30)23(17-20-12-6-2-7-13-20)27-24(29)21-14-8-3-9-15-21/h1-15,22-23,28H,16-18H2,(H,26,30)(H,27,29)/t22-,23-/m0/s1
InChIKey: KSVKECXWDNCRTM-GOTSBHOMSA-N
DeepSMILES: OC[C@@H]NC=O)[C@@H]NC=O)cccccc6))))))))Ccccccc6))))))))))Ccccccc6
Scaffold Graph/Node/Bond level: O=C(NC(Cc1ccccc1)C(=O)NCCc1ccccc1)c1ccccc1
Scaffold Graph/Node level: OC(NC(CC1CCCCC1)C(O)NCCC1CCCCC1)C1CCCCC1
Scaffold Graph level: CC(CC(CC1CCCCC1)C(C)CCCC1CCCCC1)C1CCCCC1
Functional groups: CO; CNC(C)=O; cC(=O)NC
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
NP Classifier Biosynthetic pathway: Alkaloids|Amino acids and Peptides
NP Classifier Superclass: Peptide alkaloids|Small peptides
NP Classifier Class: Dipeptides|Simple amide alkaloids
Synonymous chemical names:
aurantiamide
External chemical identifiers:
CID:CID_185904; ChEMBL:CHEMBL475827; ZINC:ZINC000006096537; SureChEMBL:SCHEMBL4372161; MolPort-035-705-667
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Aurantiamide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 402.49
Log P RDKit 2.75
Topological polar surface area (Å2) RDKit 78.43
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 20
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
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
Aurantiamide
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 Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.52
Aurantiamide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.01
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes