ChemFOnt: Showing chemical card for 4-Imidazolone-5-propionic acid (CFc000000802)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:18 UTC

Chemfont ID

CFc000000802

Molecule Identification

Common Name

4-Imidazolone-5-propionic acid

Definition

4-Imidazolone-5-propanoate is a metabolite of histidine metabolism. It is produced from urocanic acid by the enzyme urocanate hydratase [EC:4.2.1.49]. 4-Imidazolone-5-propionic acid can spontaneously decay to 4-oxoglutaramate or formylisoglutamine. It is also converted to N-forminimo-L-glutamate by the enzyme imidazolonepropionase [EC:3.5.2.7].

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4,5-Dihydro-4-oxo-5-imidazolepropanoate	ChEBI
4,5-Dihydro-5-oxo-1H-imidazole-4-propanoic acid	ChEBI
4-Imidazolone-5-propanoate	ChEBI
Imidazol-4-one-5-propionic acid	ChEBI
4,5-Dihydro-4-oxo-5-imidazolepropanoic acid	Generator
4,5-Dihydro-5-oxo-1H-imidazole-4-propanoate	Generator
4-Imidazolone-5-propanoic acid	Generator
Imidazol-4-one-5-propionate	Generator
4-Imidazolone-5-propionate	Generator
(S)-3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoate	HMDB
(S)-3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoic acid	HMDB
3-(4-oxo-4,5-Dihydro-1H-imidazol-5-yl)propanoate	HMDB
3-(4-oxo-4,5-Dihydro-1H-imidazol-5-yl)propanoic acid	HMDB
3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoate	HMDB
3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoic acid	HMDB
Imidazolone propionate	HMDB
Imidazolone propionic acid	HMDB
Imidazolonepropanoate	HMDB
Imidazolonepropanoic acid	HMDB

Chemical Formula

C₆H₈N₂O₃

Average Molecular Weight

156.1393

Monoisotopic Molecular Weight

156.053492132

IUPAC Name

3-(5-oxo-4,5-dihydro-1H-imidazol-4-yl)propanoic acid

Traditional Name

3-(5-oxo-1,4-dihydroimidazol-4-yl)propanoic acid

CAS Registry Number

17340-16-8

SMILES

OC(=O)CCC1N=CNC1=O

InChI Identifier

InChI=1S/C6H8N2O3/c9-5(10)2-1-4-6(11)8-3-7-4/h3-4H,1-2H2,(H,9,10)(H,7,8,11)

InChI Key

HEXMLHKQVUFYME-UHFFFAOYSA-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
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:27384 )
imidazolone (CHEBI:27384 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001014)

Source

Endogenous

Endogenous (HMDB: HMDB0001014)

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)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Histidine Metabolism (PathBank: SMP0063632)
Histidine Metabolism (HMDB: HMDB0001014)

Disease pathway

Histidinemia (PathBank: SMP0120493)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	10.4 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-2	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.51	ChemAxon
pKa (Strongest Basic)	4.69	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	35.22 m³·mol⁻¹	ChemAxon
Polarizability	14.27 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