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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:41 UTC
HMDB IDHMDB01014
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Imidazolone-5-propionic acid
Description4-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
Thumb
Synonyms
ValueSource
4,5-dihydro-4-oxo-5-ImidazolepropanoateChEBI
4,5-dihydro-5-oxo-1H-Imidazole-4-propanoic acidChEBI
4-Imidazolone-5-propanoateChEBI
4-Imidazolone-5-propionic acidChEBI
Imidazol-4-one-5-propionic acidChEBI
4,5-dihydro-4-oxo-5-Imidazolepropanoic acidGenerator
3-(4-oxo-4,5-dihydro-1H-Imidazol-5-yl)propanoateGenerator
4,5-dihydro-5-oxo-1H-Imidazole-4-propanoateGenerator
4-Imidazolone-5-propanoic acidGenerator
4-Imidazolone-5-propionateGenerator
Imidazol-4-one-5-propionateGenerator
(S)-3-(5-oxo-4,5-dihydro-3H-Imidazol-4-yl)propanoateHMDB
(S)-3-(5-oxo-4,5-dihydro-3H-Imidazol-4-yl)propanoic acidHMDB
3-(5-oxo-4,5-dihydro-3H-Imidazol-4-yl)propanoateHMDB
3-(5-oxo-4,5-dihydro-3H-Imidazol-4-yl)propanoic acidHMDB
Imidazolone propionateHMDB
Imidazolone propionic acidHMDB
ImidazolonepropanoateHMDB
Imidazolonepropanoic acidHMDB
Chemical FormulaC6H8N2O3
Average Molecular Weight156.1393
Monoisotopic Molecular Weight156.053492132
IUPAC Name3-(5-oxo-4,5-dihydro-1H-imidazol-4-yl)propanoic acid
Traditional Name3-(5-oxo-1,4-dihydroimidazol-4-yl)propanoic acid
CAS Registry Number17340-16-8
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 KeyInChIKey=HEXMLHKQVUFYME-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentImidazolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Imidazolyl carboxylic acid derivative
  • Imidazolinone
  • 2-imidazoline
  • Carboxamide group
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amidine
  • Amidine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.4 mg/mLALOGPS
logP-1.1ALOGPS
logP-2ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.51ChemAxon
pKa (Strongest Basic)4.69ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.76 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.22 m3·mol-1ChemAxon
Polarizability14.27 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Histidine MetabolismSMP00044map00340
HistidinemiaSMP00191Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022371
KNApSAcK IDNot Available
Chemspider ID125
KEGG Compound IDC03680
BioCyc ID4-IMIDAZOLONE-5-PROPIONATE
BiGG ID42318
Wikipedia Link4-imidazolone-5-propionic acid
NuGOwiki LinkHMDB01014
Metagene LinkHMDB01014
METLIN ID319
PubChem Compound128
PDB IDNot Available
ChEBI ID27384
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Niederwieser A, Matasovic A, Steinmann B, Baerlocher K, Kempken B: Hydantoin-5-propionic aciduria in folic acid nondependent formiminoglutamic aciduria observed in two siblings. Pediatr Res. 1976 Apr;10(4):215-9. [1272625 ]

Enzymes

General function:
Involved in urocanate hydratase activity
Specific function:
Not Available
Gene Name:
UROC1
Uniprot ID:
Q96N76
Molecular weight:
80911.275
Reactions
4-Imidazolone-5-propionic acid → Urocanic acid + Waterdetails
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in cyclic amides
Specific function:
Not Available
Gene Name:
AMDHD1
Uniprot ID:
Q96NU7
Molecular weight:
46742.505
Reactions
4-Imidazolone-5-propionic acid + Water → Formiminoglutamic acid + Hydrogen Iondetails
4-Imidazolone-5-propionic acid + Water → Formiminoglutamic aciddetails