Secondary metabolite: Putrescine-1,4-dicinnamide



Putrescine-1,4-dicinnamide
Summary
Molecular formula: C22H24N2O2
SMILES: O=C(/C=C/c1ccccc1)NCCCCNC(=O)/C=C/c1ccccc1
InChI: InChI=1S/C22H24N2O2/c25-21(15-13-19-9-3-1-4-10-19)23-17-7-8-18-24-22(26)16-14-20-11-5-2-6-12-20/h1-6,9-16H,7-8,17-18H2,(H,23,25)(H,24,26)/b15-13+,16-14+
InChIKey: NXPDEWPVRYWKQX-WXUKJITCSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Phenylpropanoids and polyketides
Class: Cinnamic acids and derivatives
Sub class: Cinnamic acid amides
Synonymous chemical names:
putrescine-1,4-dicinnamide
Chemical structure download



Putrescine-1,4-dicinnamide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 348.45
Log P RDKit 3.43
Topological polar surface area (Å2) RDKit 58.2
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 26
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 18
Number of sp3 hybridized carbon atoms RDKit 4
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.18
Shape complexity RDKit 0.18
Number of rotatable bonds SwissADME 11
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



Putrescine-1,4-dicinnamide
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’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 2
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.54



Putrescine-1,4-dicinnamide
ADMET 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 -5.77
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No




Designed by R.P. Vivek-Ananth, M Karthikeyan and Ajaya Kumar Sahoo