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Human Metabolome Database Version 3.5

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Showing metabocard for Imidazoleacetic acid (HMDB02024)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:32 -0600
Update Date 2013-02-08 17:11:12 -0700
HMDB ID HMDB02024
Secondary Accession Numbers None
Metabolite Identification
Common Name Imidazoleacetic acid
Description Imidazoleacetic acid is a metabolite product of Histamine metabolism. It is present in normal urine and increased in histidinemic patients. (PMID 6530403 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1H-Imidazol-4-ylacetic acid
  2. 1H-Imidazole-4-acetic acid
  3. 4(5)-Imidazoleacetate
  4. 4-Imidazoleacetate
  5. 4-Imidazoleacetic acid
  6. IAA
  7. IMAC
  8. Imidazol-4-ylacetic acid
  9. Imidazole acetate
  10. Imidazole-4-acetate
  11. Imidazole-4-acetic acid
  12. Imidazolyl-4-acetic acid
  13. IZC
  14. Lopac-I-0375
Chemical Formula C5H6N2O2
Average Molecular Weight 126.1133
Monoisotopic Molecular Weight 126.042927446
IUPAC Name 2-(1H-imidazol-5-yl)acetic acid
Traditional IUPAC Name 3H-imidazol-4-ylacetic acid
CAS Registry Number 645-65-8
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 Key PRJKNHOMHKJCEJ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteromonocyclic Compounds
Class Azoles
Sub Class Imidazoles
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
  • imidazole-4-carboxylic acid(ChEBI)
Substituents
  • Carboxylic Acid
Direct Parent Imidazolyl Carboxylic Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 53.3 g/L ALOGPS
LogP -0.50 ALOGPS
LogP -1.4 ChemAxon
LogS -0.37 ALOGPS
pKa (strongest acidic) 3.65 ChemAxon
pKa (strongest basic) 6.78 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 65.98 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 30.2 ChemAxon
Polarizability 11.47 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Histidine Metabolism SMP00044 map00340 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.10 +/- 0.005 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0027 +/- 0.0002 uM Adult (>18 years old) Not Specified Normal Not Available
Urine Detected and Quantified
Article_icon
2.602 (0.645-4.525) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB012464
KNApSAcK ID Not Available
Chemspider ID 86856 Link_out
KEGG Compound ID C02835 Link_out
BioCyc ID 4-IMIDAZOLEACETATE Link_out
BiGG ID 40666 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB02024 Link_out
Metagene Link HMDB02024 Link_out
METLIN ID 6445 Link_out
PubChem Compound 96215 Link_out
PDB ID Not Available
ChEBI ID 16974 Link_out
References
Synthesis Reference Madsen 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. Khandelwal JK, Prell GD, Morrishow AM, Green JP: Presence and measurement of imidazoleacetic acid, a gamma-aminobutyric acid agonist, in rat brain and human cerebrospinal fluid. J Neurochem. 1989 Apr;52(4):1107-13. Pubmed: 2926392 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. Sondergaard I: Quantitative determination of 1,4-methyl-imidazoleacetic acid in urine by high performance liquid chromatography. Allergy. 1982 Nov;37(8):581-6. Pubmed: 7181054 Link_out
Enzymes
Name: 4-trimethylaminobutyraldehyde dehydrogenase
Reactions:
  • 4-trimethylammoniobutanal + NAD+ + H2O = 4-trimethylammoniobutanoate + NADH + 2 H+ [RN:R03283]
Gene Name: ALDH9A1
Uniprot ID: P49189 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-aminoadipic semialdehyde dehydrogenase
Reactions:
  • L-2-aminoadipate 6-semialdehyde + NAD(P)+ + H2O = L-2-aminoadipate + NAD(P)H + H+ [RN:R03102 R03103]
Gene Name: ALDH7A1
Uniprot ID: P49419 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase family 1 member A3
Reactions:
  • an aldehyde + NAD(P)+ + H2O = an acid + NAD(P)H + H+ [RN:R00538 R00634]
Gene Name: ALDH1A3
Uniprot ID: P47895 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, mitochondrial
Reactions:
  • an aldehyde + NAD+ + H2O = an acid + NADH + H+ [RN:R00538]
Gene Name: ALDH2
Uniprot ID: P05091 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fatty aldehyde dehydrogenase
Reactions:
  • an aldehyde + NAD+ + H2O = an acid + NADH + H+ [RN:R00538]
Gene Name: ALDH3A2
Uniprot ID: P51648 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase X, mitochondrial
Reactions:
  • an aldehyde + NAD+ + H2O = an acid + NADH + H+ [RN:R00538]
Gene Name: ALDH1B1
Uniprot ID: P30837 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA