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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:12 UTC
Update Date2023-02-21 17:17:06 UTC
HMDB IDHMDB0004988
Secondary Accession Numbers
  • HMDB04988
Metabolite Identification
Common NamePi-Methylimidazoleacetic acid
DescriptionPi-Methylimidazoleacetic acid, also known as 1-methyl-imidazole-5-acetate or p-miaa, 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. Pi-Methylimidazoleacetic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make pi-methylimidazoleacetic acid a potential biomarker for the consumption of these foods. Pi-Methylimidazoleacetic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Pi-Methylimidazoleacetic acid.
Structure
Thumb
Synonyms
ValueSource
1-Methyl-imidazole-5-acetic acidChEBI
pros-Methylimidazoleacetic acidChEBI
1-Methyl-imidazole-5-acetateGenerator
pros-MethylimidazoleacetateGenerator
Pi-methylimidazoleacetateGenerator
p-MIAAMeSH
1-Methyl-5-imidazoleacetic acidHMDB
Pi-methylimidazoleacetic acidChEBI
1-Methyl-5-imidazoleacetateGenerator, HMDB
Chemical FormulaC6H8N2O2
Average Molecular Weight140.1399
Monoisotopic Molecular Weight140.05857751
IUPAC Name2-(1-methyl-1H-imidazol-5-yl)acetic acid
Traditional NameP-miaa
CAS Registry Number4200-48-0
SMILES
CN1C=NC=C1CC(O)=O
InChI Identifier
InChI=1S/C6H8N2O2/c1-8-4-7-3-5(8)2-6(9)10/h3-4H,2H2,1H3,(H,9,10)
InChI KeyUJCGYTCAMOHYCG-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
  • N-substituted imidazole
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Brain
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.073 +/- 0.014 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.08 +/- 0.018 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.131 (0.170-2.149) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.7 (0.26-3.35) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified8.25 +/- 4.3 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023572
KNApSAcK IDNot Available
Chemspider ID4954265
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7239
PubChem Compound6451814
PDB IDNot Available
ChEBI ID70966
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tsuruta Y, Tomida H, Kohashi K, Ohkura Y: Simultaneous determination of imidazoleacetic acid and N tau- and N pi-methylimidazoleacetic acids in human urine by high-performance liquid chromatography with fluorescence detection. J Chromatogr. 1987 Apr 24;416(1):63-9. [PubMed:3597642 ]
  2. Khandelwal JK, Hough LB, Pazhenchevsky B, Morrishow AM, Green JP: Presence and measurement of methylimidazoleacetic acids in brain and body fluids. J Biol Chem. 1982 Nov 10;257(21):12815-9. [PubMed:7130180 ]
  3. Yocum MW, Butterfield JH, Gharib H: Increased plasma calcitonin levels in systemic mast cell disease. Mayo Clin Proc. 1994 Oct;69(10):987-90. [PubMed:7934197 ]
  4. Prell GD, Green JP, Kaufmann CA, Khandelwal JK, Morrishow AM, Kirch DG, Linnoila M, Wyatt RJ: Histamine metabolites in cerebrospinal fluid of patients with chronic schizophrenia: their relationships to levels of other aminergic transmitters and ratings of symptoms. Schizophr Res. 1995 Jan;14(2):93-104. [PubMed:7711000 ]
  5. Granerus G, Roupe G, Swanbeck G: Decreased urinary histamine metabolite after successful PUVA treatment of urticaria pigmentosa. J Invest Dermatol. 1981 Jan;76(1):1-3. [PubMed:7462662 ]