IMPPAT Phytochemical information: 
N-Coumaroyl serotonin

N-Coumaroyl serotonin
Summary

SMILES: O=C(/C=C/c1ccc(cc1)O)NCCc1c[nH]c2c1cc(O)cc2
InChI: InChI=1S/C19H18N2O3/c22-15-4-1-13(2-5-15)3-8-19(24)20-10-9-14-12-21-18-7-6-16(23)11-17(14)18/h1-8,11-12,21-23H,9-10H2,(H,20,24)/b8-3+
InChIKey: WLZPAFGVOWCVMG-FPYGCLRLSA-N
DeepSMILES: O=C/C=C/cccccc6))O)))))))NCCcc[nH]cc5ccO)cc6
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: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Tryptamines 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-p-coumaroyl serotonin
External chemical identifiers:
CID:5458879; ChEMBL:CHEMBL1760547; ChEBI:175113; ZINC:ZINC000001587152; FDASRS:IUC27Q8ACH; SureChEMBL:SCHEMBL471921; MolPort-003-846-030
Chemical structure download


N-Coumaroyl serotonin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 322.36
Log P RDKit 2.95
Topological polar surface area (Å2) RDKit 85.35
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 5
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


N-Coumaroyl serotonin
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.5449


N-Coumaroyl serotonin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.14
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No