Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:12 UTC
Update Date2021-09-07 16:45:34 UTC
HMDB IDHMDB0002820
Secondary Accession Numbers
  • HMDB02820
Metabolite Identification
Common 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). Based on studies, it 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 in 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 analyzing 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 ).
Structure
Data?1582752256
Synonyms
ValueSource
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
1,4-MethylimidazoleacetateHMDB
1-Methyl-1H-imidazole-4-acetateHMDB
1-Methyl-1H-imidazole-4-acetic acidHMDB
Methylimidazole acetateHMDB
MIAAHMDB
N Tau-methylimidazoleacetic acidHMDB
Methylimidazoleacetic acid, hydrochlorideMeSH, HMDB
Chemical FormulaC6H8N2O2
Average Molecular Weight140.1399
Monoisotopic Molecular Weight140.05857751
IUPAC Name2-(1-methyl-1H-imidazol-4-yl)acetic acid
Traditional Namemethylimidazoleacetic acid
CAS Registry Number2625-49-2
SMILES
CN1C=NC(CC(O)=O)=C1
InChI Identifier
InChI=1S/C6H8N2O2/c1-8-3-5(7-4-8)2-6(9)10/h3-4H,2H2,1H3,(H,9,10)
InChI KeyZHCKPJGJQOPTLB-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 effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.66531661259
DarkChem[M-H]-128.94731661259
DeepCCS[M+H]+124.82930932474
DeepCCS[M-H]-120.99530932474
DeepCCS[M-2H]-158.39330932474
DeepCCS[M+Na]+133.87930932474
AllCCS[M+H]+130.132859911
AllCCS[M+H-H2O]+125.632859911
AllCCS[M+NH4]+134.432859911
AllCCS[M+Na]+135.632859911
AllCCS[M-H]-127.632859911
AllCCS[M+Na-2H]-129.432859911
AllCCS[M+HCOO]-131.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methylimidazoleacetic acidCN1C=NC(CC(O)=O)=C12621.3Standard polar33892256
Methylimidazoleacetic acidCN1C=NC(CC(O)=O)=C11290.1Standard non polar33892256
Methylimidazoleacetic acidCN1C=NC(CC(O)=O)=C11472.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methylimidazoleacetic acid,1TMS,isomer #1CN1C=NC(CC(=O)O[Si](C)(C)C)=C11474.9Semi standard non polar33892256
Methylimidazoleacetic acid,1TBDMS,isomer #1CN1C=NC(CC(=O)O[Si](C)(C)C(C)(C)C)=C11702.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methylimidazoleacetic acid GC-MS (1 TMS)splash10-00kb-3900000000-50b4d0d53d911c99c8192014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methylimidazoleacetic acid GC-MS (Non-derivatized)splash10-00kb-3900000000-50b4d0d53d911c99c8192017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylimidazoleacetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9400000000-0a1d81849f89413aebc82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylimidazoleacetic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0072-9200000000-be88458ee3e0fbac72bf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylimidazoleacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0005-9600000000-bfb5120a71bcb59d05952012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0002-9000000000-e8be837208f721108cb52012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00l7-9000000000-30049714cfffac75afa82012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 20V, Positive-QTOFNot Available2019-09-10HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid 40V, Positive-QTOFsplash10-0006-9000000000-dedfe29cd079d16b6ab62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid 30V, Positive-QTOFsplash10-0002-9000000000-1eb1e63625c9a88ab50e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid 30V, Positive-QTOFsplash10-0002-9000000000-2091aa9161bf50c2c4a32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid 10V, Positive-QTOFsplash10-0002-9100000000-dda19ef742ce86eb3cdc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid 30V, Positive-QTOFsplash10-0002-9000000000-1075d89ff75e92d6eb4d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid 0V, Positive-QTOFsplash10-0006-2900000000-4f104488c46146ea34152021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid 10V, Positive-QTOFsplash10-0002-9100000000-5d462295a801a6f187f22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid 0V, Positive-QTOFsplash10-0006-2900000000-9dce8cd7f849fb068b412021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid 10V, Positive-QTOFsplash10-0002-9200000000-c5783540dfb0c4f31a432021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylimidazoleacetic acid 20V, Positive-QTOFsplash10-0002-9000000000-b1629f38af1ff6c0c8812021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylimidazoleacetic acid 10V, Positive-QTOFsplash10-00di-0900000000-613db7c6c34c857875262017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylimidazoleacetic acid 20V, Positive-QTOFsplash10-00di-3900000000-b5b0ab7d260b2c465ceb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylimidazoleacetic acid 40V, Positive-QTOFsplash10-0zna-9000000000-4d40f26175c89f5ca8f12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylimidazoleacetic acid 10V, Negative-QTOFsplash10-000i-2900000000-5f3cf75dbdd1a0ff7b4e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylimidazoleacetic acid 20V, Negative-QTOFsplash10-0072-5900000000-91359fd775eb604a3d5d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylimidazoleacetic acid 40V, Negative-QTOFsplash10-0592-9300000000-24bfa38c15e2d56c8fa62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylimidazoleacetic acid 10V, Positive-QTOFsplash10-000x-6900000000-ca237928edb79864a6072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylimidazoleacetic acid 20V, Positive-QTOFsplash10-0002-9300000000-a2a472401cffb11f576f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylimidazoleacetic acid 40V, Positive-QTOFsplash10-0uea-9000000000-9a3cd80563596785356a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylimidazoleacetic acid 10V, Negative-QTOFsplash10-006t-7900000000-20650405c19d75a6a2992021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylimidazoleacetic acid 20V, Negative-QTOFsplash10-007a-4900000000-c3539a1cf8d172ae1bb42021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.08457 +/- 0.01364 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.08076 +/- 0.01892 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.02 +/- 0.001 (0.021-0.023) uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.022 +/- 0.0021 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0071 +/- 0.0009 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.50 (0.85-2.3) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.58 (0.48-2.82) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.25 (0.79-3.5) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified2.3 +/- 0.14 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleBreast cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedPancreatic cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedPeriodontal diseases details
UrineDetected and Quantified10.3 umol/mmol creatinineAdult (>18 years old)BothMastocytosis details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Pancreatic cancer
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Periodontal disease
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Mastocytosis
  1. Martens-Lobenhoffer J, Neumann HJ: Determination of 1-methylhistamine and 1-methylimidazoleacetic acid in human urine as a tool for the diagnosis of mastocytosis. J Chromatogr B Biomed Sci Appl. 1999 Jan 8;721(1):135-40. [PubMed:10027644 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023069
KNApSAcK IDNot Available
Chemspider ID68319
KEGG Compound IDC05828
BioCyc IDNot Available
BiGG ID46587
Wikipedia LinkNot Available
METLIN ID3774
PubChem Compound75810
PDB IDNot Available
ChEBI ID1606
Food Biomarker OntologyNot Available
VMH ID3MLDA
MarkerDB IDMDB00000402
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Martens-Lobenhoffer J, Neumann HJ: Determination of 1-methylhistamine and 1-methylimidazoleacetic acid in human urine as a tool for the diagnosis of mastocytosis. J Chromatogr B Biomed Sci Appl. 1999 Jan 8;721(1):135-40. [PubMed:10027644 ]
  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 ]
  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 ]
  4. 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 ]
  5. Prell GD, Khandelwal JK, Burns RS, LeWitt PA, Green JP: Elevated levels of histamine metabolites in cerebrospinal fluid of aging, healthy humans. Compr Gerontol A. 1988 Oct;2(3):114-9. [PubMed:2906817 ]
  6. 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 ]
  7. 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 ]
  8. Swahn CG, Sedvall G: Identification and determination of 1-methylimidazole-4-acetic acid in human cerebrospinal fluid by gas chromatography-mass spectrometry. J Neurochem. 1983 Mar;40(3):688-96. [PubMed:6827268 ]
  9. Johansson AC, Lonnqvist B, Granerus G: The relationship between body size and the urinary excretion of the main histamine metabolite tele-methylimidazoleacetic acid in man. Inflamm Res. 2001 Apr;50 Suppl 2:S70-1. [PubMed:11411609 ]
  10. Granerus G, Lonnqvist B, Stenstrom M: No sex difference in the urinary excretion of the histamine metabolite methylimidazoleacetic acid (MeImAA) when corrected for creatinine excretion. Inflamm Res. 1999 Apr;48 Suppl 1:S92-3. [PubMed:10350179 ]
  11. Granerus G, Lonnqvist B, Wass U: Determination of the histamine metabolite tele-methylimidazoleacetic acid and of creatinine in urine by the same HPLC system. Inflamm Res. 1999 Feb;48(2):75-80. [PubMed:10202992 ]
  12. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
Methylimidazole acetaldehyde + NAD + Water → Methylimidazoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
Methylimidazole acetaldehyde + NAD + Water → Methylimidazoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
Methylimidazole acetaldehyde + NAD + Water → Methylimidazoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
Methylimidazole acetaldehyde + NAD + Water → Methylimidazoleacetic acid + NADH + Hydrogen Iondetails