Record Information
Version1.0
Creation date2011-09-21 00:24:13 UTC
Update date2015-10-09 22:32:35 UTC
Primary IDFDB023069
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethylimidazoleacetic acid
DescriptionMethylimidazoleacetic acid is the main metabolite of histamine. This end product of histamine catabolism is formed by N-methylation in the imidazole ring to methylhistamine by histamine methyltransferase (EC 2.1.1.8) and a subsequent oxidative deamination in the side chain by type B monoamine oxidase (EC 1.4.3.4). From studies is known that as much as 70 to 80 percent of the histamine metabolized in the body is excreted in the urine as Methylimidazoleacetic acid. Thus, urinary Methylimidazoleacetic acid being the major and specific histamine metabolite is a clear marker of any changes in histamine metabolism in the body. The urinary excretion of methylimidazoleacetic acid is considered a reliable indicator of histamine turnover rate in the body. The excretion of Methylimidazoleacetic acid is higher in men than women however; this gender difference is abolished when corrected for creatinine excretion. A possible explanation is that basal histamine turnover is related to body size. There is no significant difference in Methylimidazoleacetic acid excretion between smokers and non-smokers when analysing absolute values (mg/24 h). When using Methylimidazoleacetic acid values corrected for creatinine excretion female smokers have significantly higher Methylimidazoleacetic acid excretion compared to nonsmokers. (PMID: 11411609, 7130180, 10350179, 10202992) [HMDB]
CAS Number2625-49-2
Structure
Thumb
Synonyms
SynonymSource
1,4-Methyl-imidazoleacetic acidChEBI
1-Methylimidazole-4-acetateChEBI
MethylimidazoleacetateChEBI
tele-Methylimidazoleacetic acidChEBI
1-Methyl-4-imidazoleacetic acidKegg
1,4-Methyl-imidazoleacetateGenerator
1-Methylimidazole-4-acetic acidGenerator
tele-MethylimidazoleacetateGenerator
1-Methyl-4-imidazoleacetateGenerator
Methylimidazoleacetic acid, hydrochlorideHMDB
1,4-MethylimidazoleacetateHMDB
1-Methyl-1H-imidazole-4-acetateHMDB
1-Methyl-1H-imidazole-4-acetic acidHMDB
Methylimidazole acetateHMDB
MIAAHMDB
N Tau-methylimidazoleacetic acidHMDB
2,4,5,6(1H,3H)-PyrimidinetetroneChEBI
2,4,5,6-PyrimidinetetroneChEBI
2,4,5,6-TetraoxohexahydropyrimidineChEBI
5,6-DioxouracilChEBI
5-Oxobarbituric acidChEBI
AlloxaneChEBI
MesoxalylcarbamideChEBI
MesoxalylureaChEBI
NSC 7169ChEBI
PyrimidinetetroneChEBI
5-OxobarbitateGenerator
5-Oxobarbitic acidGenerator
2,4,5,6-PyrimidintetronHMDB
2,4,5,6-PyrimidintetroneHMDB
5-oxo-BarbiturateHMDB
5-oxo-Barbituric acidHMDB
Alloxan 7169HMDB
Alloxan tetrahydratHMDB
Mesoxalyl-ureaHMDB
3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dioneChEBI
3,7-Dimethylpurine-2,6-dioneChEBI
3,7-DimethylxanthineChEBI
TheobrominChEBI
TeobrominHMDB
2,6-Dihydroxy-3,7-dimethyl-purineHMDB
3,7-Dimethyl-xanthineHMDB
DiurobromineHMDB
1-(9Z-Octadecenoyl)-sn-glycero-3-phosphocholineChEBI
1-Oleoyl-2-hydroxy-sn-glycero-3-phosphocholineChEBI
1-Oleoyl-sn-glycero-3-phosphorylcholineChEBI
1-OleoylglycerophosphocholineChEBI
3-Oleoyl-rac-glycerol-1-phosphorylcholineChEBI
LPC 18:1ChEBI
LPC 18:1(9Z)/0:0ChEBI
LPC(18:1(9Z)/0:0)ChEBI
LysoPC 18:1(9Z)/0:0ChEBI
LysoPC(18:1(9Z)/0:0)ChEBI
Lysophosphatidylcholine 18:1ChEBI
Lysophosphatidylcholine(18:1(9Z)/0:0)ChEBI
PC 18:1(9Z)/0:0ChEBI
PC(18:1(9Z)/0:0)ChEBI
1-(9Z)-Octadecenoyl-sn-glycero-3-phosphocholineHMDB
1-Oleoyl-sn-glycero-3-phosphocholineHMDB
Choline phosphate (ester) 3-ester with 1-monooleinHMDB
Choline phosphate 3-ester with 1-monooleinHMDB
Gpcho(18:1(9Z)/0:0)[rac]HMDB
LPC(18:1n9/0:0)HMDB
LPC(18:1W9/0:0)HMDB
LyPC(18:1)HMDB
LyPC(18:1/0:0)HMDB
LyPC(18:1W9/0:0)HMDB
LysoPC a C18:1HMDB
LysoPC(18:1)HMDB
LysoPC(18:1n9/0:0)HMDB
LysoPC(18:1W9/0:0)HMDB
Lysophosphatidylcholine(18:1)HMDB
Lysophosphatidylcholine(18:1/0:0)HMDB
Lysophosphatidylcholine(18:1n9/0:0)HMDB
Lysophosphatidylcholine(18:1W9/0:0)HMDB
LysoPIC(18:1/0:0)HMDB
Olein-1-mono-3-phosphate ester with cholineHMDB
Oleoyl lysolecithinHMDB
Oleoyl lysophosphatidylcholineHMDB
1-(cis-9-Octadecenoyl)-sn-glycero-3-phosphocholineHMDB
1-OGPCHMDB
1-Oleoyl lysophosphatidylcholineHMDB
1-Oleoyl-lysopcHMDB
1-Oleoyl-glycero-3-phosphocholineHMDB
LysoPC(18:1/0:0)HMDB
LPC(18:1/0:0)HMDB
LPC(18:1)HMDB
1-(9Z-Octadecenoyl)-glycero-3-phosphocholineHMDB
1-methyl-1H-Imidazole-4-acetatehmdb
1-methyl-1H-Imidazole-4-acetic acidhmdb
1,4-methyl-imidazoleacetic acidhmdb
Methylimidazoleacetic acidhmdb
N tau-methylimidazoleacetic acidhmdb
Tele-methylimidazoleacetatehmdb
Tele-methylimidazoleacetic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility5.88 g/LALOGPS
logP-0.22ALOGPS
logP-1.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)6.45ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.12 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity34.85 m³·mol⁻¹ChemAxon
Polarizability13.69 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H8N2O2
IUPAC name2-(1-methyl-1H-imidazol-4-yl)acetic acid
InChI IdentifierInChI=1S/C6H8N2O2/c1-8-3-5(7-4-8)2-6(9)10/h3-4H,2H2,1H3,(H,9,10)
InChI KeyZHCKPJGJQOPTLB-UHFFFAOYSA-N
Isomeric SMILESCN1C=NC(CC(O)=O)=C1
Average Molecular Weight140.1399
Monoisotopic Molecular Weight140.05857751
Classification
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 effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00kb-3900000000-50b4d0d53d911c99c819View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kb-3900000000-50b4d0d53d911c99c819View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9400000000-0a1d81849f89413aebc8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0072-9200000000-be88458ee3e0fbac72bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0005-9600000000-bfb5120a71bcb59d0595View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-9000000000-e8be837208f721108cb5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00l7-9000000000-30049714cfffac75afa8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 20V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-613db7c6c34c85787526View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3900000000-b5b0ab7d260b2c465cebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zna-9000000000-4d40f26175c89f5ca8f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2900000000-5f3cf75dbdd1a0ff7b4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0072-5900000000-91359fd775eb604a3d5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0592-9300000000-24bfa38c15e2d56c8fa6View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID68319
ChEMBL IDNot Available
KEGG Compound IDC05828
Pubchem Compound ID75810
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02820
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID46587
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Histidine MetabolismSMP00044 map00340
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference