ChemFOnt: Showing chemical card for 3,4,5-Trimethoxycinnamic acid (CFc000001649)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:19 UTC

Chemfont ID

CFc000001649

Molecule Identification

Common Name

3,4,5-Trimethoxycinnamic acid

Definition

3, 4, 5-trimethoxycinnamic acid is a methoxycinnamic acid with three methoxy substituents at the 3-, 4- and 5-positions. It has a role as an allergen. It is a conjugate acid of a 3,4,5-trimethoxycinnamate. 3, 4, 5-Trimethoxycinnamic acid is an organic acid found in normal human urine (PMID:6992730 , 6511847 ). Trimethoxycinnamate is a natural aromatic ester from Piper longum that inhibits expression of cell adhesion molecules on endothelial cells (TNF- -induced expression of intercellular adhesion molecule-1 (ICAM-1) and E-Selectin and vascular adhesion molecules-1 (VCAM-1)), without being toxic to endothelial cells. (PMID:16313198 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4,5-Trimethoxycinnamate	Generator
3-(3,4,5-Trimethoxyphenyl)-2-propenoic acid	MeSH
3,4,5-Trimethoxy cinnamate	HMDB
3,4,5-Trimethoxy cinnamic acid	HMDB
3,4,5-Trimethoxyphenylacrylate	HMDB
3,4,5-Trimethoxyphenylacrylic acid	HMDB
O-Methylsinapate	HMDB
O-Methylsinapic acid	HMDB
(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoate	Generator, HMDB
3,4,5-Trimethoxycinnamic acid	MeSH

Chemical Formula

C₁₂H₁₄O₅

Average Molecular Weight

238.2366

Monoisotopic Molecular Weight

238.084123558

IUPAC Name

(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid

Traditional Name

3,4,5-trimethoxycinnamic acid

CAS Registry Number

90-50-6

SMILES

COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b5-4+

InChI Key

YTFVRYKNXDADBI-SNAWJCMRSA-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
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

Not Available

Functional Ontology

Not Available

Urine (PMID: 19812218)

Source

Endogenous

Endogenous (HMDB: HMDB0002511)

Plant

Plant (HMDB: HMDB0002511)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	2.24	ALOGPS
logP	1.66	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.45 m³·mol⁻¹	ChemAxon
Polarizability	24.17 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

External Links

HMDB ID

HMDB0002511

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023019

KNApSAcK ID

Not Available

Chemspider ID

642910

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6705

PubChem Compound

735755

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3,4,5-Trimethoxycinnamic acid (CFc000001649)

MOL for CFc000001649 (3,4,5-Trimethoxycinnamic acid)

3D MOL for CFc000001649 (3,4,5-Trimethoxycinnamic acid)

3D SDF for CFc000001649 (3,4,5-Trimethoxycinnamic acid)

3D-SDF for CFc000001649 (3,4,5-Trimethoxycinnamic acid)

PDB for CFc000001649 (3,4,5-Trimethoxycinnamic acid)

3D PDB for CFc000001649 (3,4,5-Trimethoxycinnamic acid)

SMILES for CFc000001649 (3,4,5-Trimethoxycinnamic acid)

INCHI for CFc000001649 (3,4,5-Trimethoxycinnamic acid)

Structure for CFc000001649 (3,4,5-Trimethoxycinnamic acid)

3D Structure for CFc000001649 (3,4,5-Trimethoxycinnamic acid)