IMPPAT Phytochemical information: 
Dicaffeoylputrescine
Dicaffeoylputrescine
Summary

SMILES: O=C(/C=C/c1ccc(c(c1)O)O)NCCCCNC(=O)/C=C/c1ccc(c(c1)O)O
InChI: InChI=1S/C22H24N2O6/c25-17-7-3-15(13-19(17)27)5-9-21(29)23-11-1-2-12-24-22(30)10-6-16-4-8-18(26)20(28)14-16/h3-10,13-14,25-28H,1-2,11-12H2,(H,23,29)(H,24,30)/b9-5+,10-6+
InChIKey: WKIWXOKCKNMLIX-NXZHAISVSA-N
DeepSMILES: O=C/C=C/cccccc6)O))O)))))))NCCCCNC=O)/C=C/cccccc6)O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)NCCCCNC(=O)C=Cc1ccccc1
Scaffold Graph/Node level: OC(CCC1CCCCC1)NCCCCNC(O)CCC1CCCCC1
Scaffold Graph level: CC(CCCCCCC(C)CCC1CCCCC1)CCC1CCCCC1
Functional groups: c/C=C/C(=O)NC; 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: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Polyamines
Synonymous chemical names:
dicaffeoylputrescine
External chemical identifiers:
CID:CID_11538839; ChEMBL:CHEMBL197015; ChEBI:CHEBI:175300; SureChEMBL:SCHEMBL10735083
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Dicaffeoylputrescine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 412.44
Log P RDKit 2.25
Topological polar surface area (Å2) RDKit 139.12
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 8
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
Shape complexity RDKit 0.18
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 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
Dicaffeoylputrescine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.212131
Dicaffeoylputrescine
ADME 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 -7.08
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No