IMPPAT Phytochemical information: 
4-Hydroxycinnamic acid hexadecyl ester

4-Hydroxycinnamic acid hexadecyl ester
Summary

SMILES: CCCCCCCCCCCCCCCCOC(=O)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C25H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-22-28-25(27)21-18-23-16-19-24(26)20-17-23/h16-21,26H,2-15,22H2,1H3/b21-18+
InChIKey: UYRIBRFIGLHCHE-DYTRJAOYSA-N
DeepSMILES: CCCCCCCCCCCCCCCCOC=O)/C=C/cccccc6))O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: c/C=C/C(=O)OC; 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: Shikimates and Phenylpropanoids
Synonymous chemical names:
hexadecyl p-coumarate
External chemical identifiers:
CID:CID_20815819; SureChEMBL:SCHEMBL6397875
Chemical structure download


4-Hydroxycinnamic acid hexadecyl ester
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 388.59
Log P RDKit 7.43
Topological polar surface area (Å2) RDKit 46.53
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 3
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 16
Shape complexity RDKit 0.64
Number of rotatable bonds RDKit 18
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


4-Hydroxycinnamic acid hexadecyl ester
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.17


4-Hydroxycinnamic acid hexadecyl ester
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 -1.85
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