IMPPAT Phytochemical information: 
Eicosanyl caffeate

Eicosanyl caffeate
Summary

SMILES: CCCCCCCCCCCCCCCCCCCCOC(=O)/C=C/c1ccc(c(c1)O)O
InChI: InChI=1S/C29H48O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24-33-29(32)23-21-26-20-22-27(30)28(31)25-26/h20-23,25,30-31H,2-19,24H2,1H3/b23-21+
InChIKey: LTSJTDDQUOUKJT-XTQSDGFTSA-N
DeepSMILES: CCCCCCCCCCCCCCCCCCCCOC=O)/C=C/cccccc6)O))O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: cO; c/C=C/C(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
ClassyFire Subclass: Hydroxycinnamic acids and derivatives
Synonymous chemical names:
eicosanyl caffeate
External chemical identifiers:
CID:CID_5320238; ZINC:ZINC000085613199
Chemical structure download


Eicosanyl caffeate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 460.7
Log P RDKit 8.7
Topological polar surface area (Å2) RDKit 66.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
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 9
Number of sp3 hybridized carbon atoms RDKit 20
Shape complexity RDKit 0.69
Number of rotatable bonds RDKit 22
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 1
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 1


Eicosanyl caffeate
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 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.0832828


Eicosanyl caffeate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -0.45
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No