ChemFOnt: Showing chemical card for 3-(3,4-Dimethoxyphenyl)-2-propenoic acid (CFc000015392)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:04:32 UTC

Chemfont ID

CFc000015392

Molecule Identification

Common Name

3-(3,4-Dimethoxyphenyl)-2-propenoic acid

Definition

3-(3,4-Dimethoxyphenyl)-2-propenoic acid is found in beverages. 3-(3,4-Dimethoxyphenyl)-2-propenoic acid is found in kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(3,4-Dimethoxyphenyl)-2-propenoate	Generator
3-(3,4-Dimethoxyphenyl)propenoic acid	MeSH
3-(3,4-Dimethoxyphenyl)propenoic acid, (e)-isomer	MeSH
oo'-Dimethylcaffeic acid	ChEMBL, HMDB
oo'-Dimethylcaffeate	Generator, HMDB
(2E)-3-(3,4-Dimethoxyphenyl)-2-propenoic acid	HMDB
(2E)-3-(3,4-Dimethoxyphenyl)acrylic acid	HMDB
(2E)-3-(3,4-Dimethoxyphenyl)prop-2-enoic acid	HMDB
(e)-3',4'-Dimethoxycinnamic acid	HMDB
(e)-3,4-Dimethoxycinnamic acid	HMDB
3, 4-Dimethoxycinnamic acid	HMDB
3,4-Dimethoxy-cinnamic acid	HMDB
3,4-Dimethoxy-trans-cinnamic acid	HMDB
3,4-Dimethoxycinnamic acid	HMDB
3,4-Dimethoxycinnamic acid, 8ci	HMDB
3,4-Dimethoxycinnamic acid, predominantly trans	HMDB
3,4-Dimethoxyphenyl-2-propenoic acid	HMDB
3-(3,4-Dimethoxyphenyl)-(e)-2-propenoic acid	HMDB
3-(3,4-Dimethoxyphenyl)-2-propenoic acid, 9ci	HMDB
Caffeic acid dimethyl ether	HMDB
Dimethyl caffeic acid	HMDB
Dimethylcaffeic acid	HMDB
e)-3,4-Dimethoxycinnamic acid	HMDB
3,4-Dimethoxycinnamate	Generator

Chemical Formula

C₁₁H₁₂O₄

Average Molecular Weight

208.2106

Monoisotopic Molecular Weight

208.073558872

IUPAC Name

(2E)-3-(3,4-dimethoxyphenyl)prop-2-enoic acid

Traditional Name

cinnamic acid,3,4-dimethoxy

CAS Registry Number

14737-89-4

SMILES

COC1=C(OC)C=C(\C=C\C(O)=O)C=C1

InChI Identifier

InChI=1S/C11H12O4/c1-14-9-5-3-8(4-6-11(12)13)7-10(9)15-2/h3-7H,1-2H3,(H,12,13)/b6-4+

InChI Key

HJBWJAPEBGSQPR-GQCTYLIASA-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

Cinnamic acid
Coumaric acid or derivatives
O-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

methoxycinnamic acid (CHEBI:86549 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 19812218)

Excreta

Biofluid or Excreta

Urine (PMID: 19812218)

Cellular substructure

Extracellular (HMDB: HMDB0034315)
Cytoplasm (HMDB: HMDB0034315)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034315)

Source

Exogenous

Exogenous (HMDB: HMDB0034315)

Food

Food (HMDB: HMDB0034315)

Herb and spice

Spice

Wasabi (FooDB: FOOD00498)

Beverage

Beverages (FooDB: FOOD00870)

Endogenous

Plant

Plant (HMDB: HMDB0034315)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034315)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	2.5	ALOGPS
logP	1.82	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.99 m³·mol⁻¹	ChemAxon
Polarizability	21.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon