ChemFOnt: Showing chemical card for Caffeic acid phenethyl ester (CFc000229066)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:55:28 UTC

Chemfont ID

CFc000229066

Molecule Identification

Common Name

Caffeic acid phenethyl ester

Definition

2-phenylethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Based on a literature review very few articles have been published on 2-phenylethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Phenylethyl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator
3,4-Dihydroxycinnamate phenethyl ester	Generator, HMDB
2-Propenoate, 3-(3,4-dihydroxyphenyl)-, 2-phenylethyl ester	Generator

Chemical Formula

C₁₇H₁₆O₄

Average Molecular Weight

284.311

Monoisotopic Molecular Weight

284.104858995

IUPAC Name

2-phenylethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

2-phenylethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=CC(=O)OCCC2=CC=CC=C2)C=C1O

InChI Identifier

InChI=1S/C17H16O4/c18-15-8-6-14(12-16(15)19)7-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2

InChI Key

SWUARLUWKZWEBQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.063 g/L	ALOGPS
logP	3.65	ALOGPS
logP	3.92	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	81.16 m³·mol⁻¹	ChemAxon
Polarizability	30.75 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0249532

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

97147

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108042

PDB ID

Not Available

ChEBI ID

93478

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Caffeic acid phenethyl ester (CFc000229066)

MOL for CFc000229066 (Caffeic acid phenethyl ester)

3D MOL for CFc000229066 (Caffeic acid phenethyl ester)

3D SDF for CFc000229066 (Caffeic acid phenethyl ester)

3D-SDF for CFc000229066 (Caffeic acid phenethyl ester)

PDB for CFc000229066 (Caffeic acid phenethyl ester)

3D PDB for CFc000229066 (Caffeic acid phenethyl ester)

SMILES for CFc000229066 (Caffeic acid phenethyl ester)

INCHI for CFc000229066 (Caffeic acid phenethyl ester)

Structure for CFc000229066 (Caffeic acid phenethyl ester)

3D Structure for CFc000229066 (Caffeic acid phenethyl ester)