IMPPAT Phytochemical information: 
Nb-p-Coumaroyltryptamine
Nb-p-Coumaroyltryptamine
Summary

SMILES: O=C(/C=C/c1ccc(cc1)O)NCCc1c[nH]c2c1cccc2
InChI: InChI=1S/C19H18N2O2/c22-16-8-5-14(6-9-16)7-10-19(23)20-12-11-15-13-21-18-4-2-1-3-17(15)18/h1-10,13,21-22H,11-12H2,(H,20,23)/b10-7+
InChIKey: CDMGLLBADMBULG-JXMROGBWSA-N
DeepSMILES: O=C/C=C/cccccc6))O)))))))NCCcc[nH]cc5cccc6
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)NCCc1c[nH]c2ccccc12
Scaffold Graph/Node level: OC(CCC1CCCCC1)NCCC1CNC2CCCCC12
Scaffold Graph level: CC(CCCC1CCC2CCCCC21)CCC1CCCCC1
Functional groups: c/C=C/C(=O)NC; cO; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
ClassyFire Subclass: Hydroxycinnamic acids and derivatives
NP Classifier Biosynthetic pathway: Amino acids and Peptides|Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acid amides
Synonymous chemical names:
n-feruloyltryptamine
External chemical identifiers:
CID:CID_5458878; ChEMBL:CHEMBL488849; ChEBI:CHEBI:174932; ZINC:ZINC000014824027; SureChEMBL:SCHEMBL798186; MolPort-037-379-375
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Nb-p-Coumaroyltryptamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 306.37
Log P RDKit 3.25
Topological polar surface area (Å2) RDKit 65.12
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
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 17
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.11
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 1
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
Nb-p-Coumaroyltryptamine
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 0.63355
Nb-p-Coumaroyltryptamine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -6.26
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 Yes