ChemFOnt: Showing chemical card for Imidazoleacrylic acid (CFc000334765)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:26:52 UTC

Chemfont ID

CFc000334765

Molecule Identification

Common Name

Imidazoleacrylic acid

Definition

Trans-urocanic acid, also known as 4-imidazoleacrylic acid or urocanate, belongs to imidazolyl carboxylic acids and derivatives class of compounds. Those are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. Trans-urocanic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Trans-urocanic acid can be found in mung bean, which makes trans-urocanic acid a potential biomarker for the consumption of this food product. Trans-urocanic acid can be found primarily in most biofluids, including sweat, feces, blood, and urine, as well as in human liver and skin tissues. Trans-urocanic acid exists in all living organisms, ranging from bacteria to humans. In humans, trans-urocanic acid is involved in the histidine metabolism. Trans-urocanic acid is also involved in a couple of metabolic disorders, which include ammonia recycling and histidinemia.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-3-(1H-Imidazol-4-yl)acrylic acid	ChEBI
(e)-3-(1H-Imidazol-4-yl)-2-propenoic acid	ChEBI
(2E)-3-(1H-Imidazol-4-yl)acrylate	Generator
(e)-3-(1H-Imidazol-4-yl)-2-propenoate	Generator
Urocanate	Generator
3-(1H-Imidazol-4-yl)-2-propenoate	HMDB
3-(1H-Imidazol-4-yl)-2-propenoic acid	HMDB
3-(1H-Imidazol-4-yl)acrylate	HMDB
3-(1H-Imidazol-4-yl)acrylic acid	HMDB
3-(4-Imidazolyl)acrylate	HMDB
3-(4-Imidazolyl)acrylic acid	HMDB
5-Imidazoleacrylate	HMDB
5-Imidazoleacrylic acid	HMDB
Imidazole-4-acrylate	HMDB
Imidazole-4-acrylic acid	HMDB
Imidazoleacrylic acid	HMDB
Acid, glyoxalinylacrylic	HMDB
Acid, urocanic	HMDB
Glyoxalinylacrylic acid	HMDB
(2E)-3-(1H-Imidazol-5-yl)-2-propenoic acid	HMDB
(e)-3-(4-Imidazolyl)acrylic acid	HMDB
(e)-3-(Imidazol-4-yl)-2-propenoic acid	HMDB
(e)-Urocanic acid	HMDB
trans-Urocanic acid	HMDB

Chemical Formula

C₆H₆N₂O₂

Average Molecular Weight

138.124

Monoisotopic Molecular Weight

138.042927446

IUPAC Name

(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid

Traditional Name

trans-urocanic acid

CAS Registry Number

3465-72-3

SMILES

OC(=O)\C=C\C1=CNC=N1

InChI Identifier

InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+

InChI Key

LOIYMIARKYCTBW-OWOJBTEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Imidazolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Imidazolyl carboxylic acid derivative
Heteroaromatic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

urocanic acid (CHEBI:30817 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000301)
Extracellular (HMDB: HMDB0000301)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000301)
Saliva (HMDB: HMDB0000301)

Excreta

Biofluid or Excreta

Organ

Liver (HMDB: HMDB0000301)
Skin (HMDB: HMDB0000301)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000301)

Source

Endogenous

Endogenous (HMDB: HMDB0000301)

Plant

Plant (HMDB: HMDB0000301)
Fabaceae (HMDB: HMDB0000301)

Exogenous

Food

Food (HMDB: HMDB0000301)

Animal origin

Poultry

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)

Pulse

Bean

Mung bean (FooDB: FOOD00200)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Ammonia Recycling (HMDB: HMDB0000301)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000301)

Biological role

Nutrient (HMDB: HMDB0000301)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	42.5 g/L	ALOGPS
logP	0.22	ALOGPS
logP	-1	ChemAxon
logS	-0.51	ALOGPS
pKa (Strongest Acidic)	3.85	ChemAxon
pKa (Strongest Basic)	6.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	35.57 m³·mol⁻¹	ChemAxon
Polarizability	13.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon