IMPPAT Phytochemical information: 
N-trans-p-Coumaroyloctopamine
N-trans-p-Coumaroyloctopamine
Summary

SMILES: O=C(NCC(c1ccc(cc1)O)O)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C17H17NO4/c19-14-6-1-12(2-7-14)3-10-17(22)18-11-16(21)13-4-8-15(20)9-5-13/h1-10,16,19-21H,11H2,(H,18,22)/b10-3+
InChIKey: VATOSFCFMOPAHX-XCVCLJGOSA-N
DeepSMILES: O=CNCCcccccc6))O)))))O))))/C=C/cccccc6))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)NCCc1ccccc1
Scaffold Graph/Node level: OC(CCC1CCCCC1)NCCC1CCCCC1
Scaffold Graph level: CC(CCCC1CCCCC1)CCC1CCCCC1
Functional groups: c/C=C/C(=O)NC; cO; CO
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-trans- p-coumaroyloctopamine
External chemical identifiers:
CID:CID_23874492; MolPort-001-740-424
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
N-trans-p-Coumaroyloctopamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 299.33
Log P RDKit 1.96
Topological polar surface area (Å2) RDKit 89.79
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.12
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
N-trans-p-Coumaroyloctopamine
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 0.635363
N-trans-p-Coumaroyloctopamine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.88
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No