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Record Information
Version1.0
Creation Date2016-09-30 22:50:04 UTC
Update Date2020-05-11 20:39:46 UTC
MCDB ID BMDB0002024
Secondary Accession Numbers
  • BMDB02024
Metabolite Identification
Common NameImidazoleacetic acid
DescriptionImidazoleacetic acid, also known as 4(5)-imidazoleacetate or imac, 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. Imidazoleacetic acid is possibly soluble (in water) and a very strong basic compound (based on its pKa). Imidazoleacetic acid exists in all living organisms, ranging from bacteria to humans. Imidazoleacetic acid can be biosynthesized from imidazole-4-acetaldehyde through the action of the enzyme aldehyde dehydrogenase, mitochondrial. In cattle, imidazoleacetic acid is involved in the metabolic pathway called the histidine metabolism pathway. Imidazoleacetic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
1H-Imidazole-4-acetic acidChEBI
4(5)-ImidazoleacetateChEBI
4-ImidazoleacetateChEBI
Imidazole-4-acetateChEBI
1H-Imidazole-4-acetateGenerator
4(5)-Imidazoleacetic acidGenerator
4-Imidazoleacetic acidGenerator
Imidazole-4-acetic acidGenerator
ImidazoleacetateGenerator
1H-Imidazol-4-ylacetic acidHMDB
IAAHMDB
IMACHMDB
Imidazol-4-ylacetateHMDB
Imidazol-4-ylacetic acidHMDB
Imidazole acetateHMDB
Imidazolyl-4-acetic acidHMDB
IZCHMDB
Lopac-I-0375HMDB
Imidazole-4-acetic acid, sodium saltHMDB
Imidazole-4-acetic acid hydrochlorideHMDB
Chemical FormulaC5H6N2O2
Average Molecular Weight126.1133
Monoisotopic Molecular Weight126.042927446
IUPAC Name2-(1H-imidazol-5-yl)acetic acid
Traditional NameIMAC
CAS Registry Number645-65-8
SMILES
OC(=O)CC1=CN=CN1
InChI Identifier
InChI=1S/C5H6N2O2/c8-5(9)1-4-2-6-3-7-4/h2-3H,1H2,(H,6,7)(H,8,9)
InChI KeyPRJKNHOMHKJCEJ-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentImidazolyl 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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.5ALOGPS
logP-1.4ChemAxon
logS-0.37ALOGPS
pKa (Strongest Acidic)3.65ChemAxon
pKa (Strongest Basic)6.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.98 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity30.2 m³·mol⁻¹ChemAxon
Polarizability11.47 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0002024
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030508
KNApSAcK IDNot Available
Chemspider ID86856
KEGG Compound IDC02835
BioCyc ID4-IMIDAZOLEACETATE
BiGG ID40666
Wikipedia LinkNot Available
METLIN ID6445
PubChem Compound96215
PDB IDNot Available
ChEBI ID16974
References
Synthesis ReferenceMadsen Christian; Jensen Anders A; Liljefors Tommy; Kristiansen Uffe; Nielsen Birgitte; Hansen Camilla P; Larsen Mogens; Ebert Bjarke; Bang-Andersen Benny; Krogsgaard-Larsen Povl; Frolund Bente 5-Substituted imidazole-4-acetic acid analogues: synthesis, modeling, and pharmacological characterization of a series of novel gamma-aminobutyric acid(C) receptor agonists. Journal of medicinal chemistry (2007), 50(17), 4147-61.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]