ChemFOnt: Showing chemical card for N-cis-feruloyltyramine (CFc000017368)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:07:19 UTC

Chemfont ID

CFc000017368

Molecule Identification

Common Name

N-cis-feruloyltyramine

Definition

N-cis-feruloyltyramine or cis-N-Feruloyltyramine (CFT) belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is also classified as a phenylpropanoid amide. Phenylpropanoids consist of a six-carbon, aromatic phenyl group and a three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. A phenylpropanoid amide has an amide group incorporated into its propanoid chain. There are two known isomers of N-Feruloyltyramine, N-trans-Feruloyltyramine and N-cis-Feruloyltyramine. Moupinamide is a largely neutral molecule, that is somewhat insoluble in water. It exists as a pale yellow oil. N-cis-Feruloyltyramine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases, they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. N-cis-Feruloyltyramine has been found within a few different foods or plants (especially their stems), such as yellow bell peppers, red bell peppers, orange bell peppers and green bell peppers (Capsicum annuum) (PMID: 21425680 ). This could make N-cis-feruloyltyramine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-cis-Feruloyltyramine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
cis-N-Feruloyltyramine	HMDB
N-cis-Feruloyl tyramine	HMDB
(2Z)-3-(4-Hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidate	HMDB
N-cis-Feruloyltyramine	HMDB
(2,3) cis-N-(P-Hydroxyphenethyl)ferulamide	HMDB
(2Z)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-2-propenamide	HMDB
(2Z)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide	HMDB
Feruloyltyramine	HMDB
Feruloyltyramine, (Z)-isomer	HMDB
NCT	HMDB
N-[(Z)-Feruloyl]tyramine	HMDB
N-Feruloyltyramine	HMDB
3-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxyphenyl)ethyl)-2-Propenamide	HMDB

Chemical Formula

C₁₈H₁₉NO₄

Average Molecular Weight

313.3478

Monoisotopic Molecular Weight

313.131408101

IUPAC Name

(Z,2Z)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]propa-2-enimidic acid

Traditional Name

(Z,2Z)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]propa-2-enimidic acid

CAS Registry Number

80510-09-4

SMILES

COC1=C(O)C=CC(\C=C/C(/O)=N/CCC2=CC=C(O)C=C2)=C1

InChI Identifier

InChI=1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5-

InChI Key

NPNNKDMSXVRADT-UITAMQMPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid amide
Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036381)
Cytoplasm (HMDB: HMDB0036381)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036381)

Source

Exogenous

Exogenous (HMDB: HMDB0036381)

Food

Food (HMDB: HMDB0036381)

Fruit

Tropical fruit

Cherimoya (FooDB: FOOD00326)

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0036381)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036381)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	3.12	ALOGPS
logP	3.62	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.58	ChemAxon
pKa (Strongest Basic)	4.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.28 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	90.09 m³·mol⁻¹	ChemAxon
Polarizability	33.82 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

HMDB0036381

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015259

KNApSAcK ID

C00025324

Chemspider ID

4944914

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440659

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N-cis-feruloyltyramine (CFc000017368)

MOL for CFc000017368 (N-cis-feruloyltyramine)

3D MOL for CFc000017368 (N-cis-feruloyltyramine)

3D SDF for CFc000017368 (N-cis-feruloyltyramine)

3D-SDF for CFc000017368 (N-cis-feruloyltyramine)

PDB for CFc000017368 (N-cis-feruloyltyramine)

3D PDB for CFc000017368 (N-cis-feruloyltyramine)

SMILES for CFc000017368 (N-cis-feruloyltyramine)

INCHI for CFc000017368 (N-cis-feruloyltyramine)

Structure for CFc000017368 (N-cis-feruloyltyramine)

3D Structure for CFc000017368 (N-cis-feruloyltyramine)