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Showing metabocard for Methylimidazoleacetic acid (HMDB0002820)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:12 UTC
Update Date2023-02-21 17:16:28 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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002820 (Methylimidazoleacetic acid)

  Mrv1652305271900212D          

 10 10  0  0  0  0            999 V2000
   28.6185  -15.5904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3130  -16.1716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5716  -18.9485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1591  -17.6790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4691  -17.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5716  -19.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1335  -16.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9841  -17.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9042  -18.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2391  -18.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  7  2  0  0  0  0
  3  6  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
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3D MOL for HMDB0002820 (Methylimidazoleacetic acid)

HMDB0002820
     RDKit          3D
Methylimidazoleacetic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.8835    0.7267   -0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6336   -0.0382   -0.0890 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5018   -1.3374    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -1.6449    0.0535 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4730   -0.5390   -0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263   -0.4511   -0.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6397   -0.1926    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605   -1.0257    1.6544 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2424    1.0500    0.9231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4357    0.4785   -0.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7920    1.6419   -0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1449    1.0066    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6991    0.0859   -0.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064   -2.0108    0.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1269    0.4053   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3446   -1.3598   -1.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2558    1.7242    0.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767    1.4803   -0.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  6 15  1  0
  6 16  1  0
  9 17  1  0
 10 18  1  0
M  END
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3D SDF for HMDB0002820 (Methylimidazoleacetic acid)

  Mrv1652305271900212D          

 10 10  0  0  0  0            999 V2000
   28.6185  -15.5904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3130  -16.1716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5716  -18.9485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1591  -17.6790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4691  -17.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5716  -19.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1335  -16.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9841  -17.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9042  -18.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2391  -18.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  7  2  0  0  0  0
  3  6  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002820

> <DATABASE_NAME>
hmdb

> <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_KEY>
ZHCKPJGJQOPTLB-UHFFFAOYSA-N

> <FORMULA>
C6H8N2O2

> <MOLECULAR_WEIGHT>
140.1399

> <EXACT_MASS>
140.05857751

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.685673940215624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(1-methyl-1H-imidazol-4-yl)acetic acid

> <ALOGPS_LOGP>
-0.22

> <JCHEM_LOGP>
-1.1630740442859269

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6846478765551316

> <JCHEM_PKA_STRONGEST_BASIC>
6.4534930755175495

> <JCHEM_POLAR_SURFACE_AREA>
55.12

> <JCHEM_REFRACTIVITY>
34.845099999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylimidazoleacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0002820 (Methylimidazoleacetic acid)

HMDB0002820
     RDKit          3D
Methylimidazoleacetic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.8835    0.7267   -0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6336   -0.0382   -0.0890 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5018   -1.3374    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1954   -1.6449    0.0535 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4730   -0.5390   -0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263   -0.4511   -0.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6397   -0.1926    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605   -1.0257    1.6544 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2424    1.0500    0.9231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4357    0.4785   -0.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7920    1.6419   -0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1449    1.0066    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6991    0.0859   -0.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064   -2.0108    0.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1269    0.4053   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3446   -1.3598   -1.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2558    1.7242    0.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767    1.4803   -0.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  6 15  1  0
  6 16  1  0
  9 17  1  0
 10 18  1  0
M  END
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PDB for HMDB0002820 (Methylimidazoleacetic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      53.421 -29.102   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      50.984 -30.187   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      51.467 -35.371   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      50.697 -33.001   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      53.142 -31.755   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      51.467 -36.911   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      52.516 -30.348   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      52.237 -33.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      50.221 -34.465   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      52.713 -34.465   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    6    9   10                                                  
CONECT    4    8    9                                                       
CONECT    5    7    8                                                       
CONECT    6    3                                                            
CONECT    7    1    2    5                                                  
CONECT    8    4    5   10                                                  
CONECT    9    3    4                                                       
CONECT   10    3    8                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0002820 (Methylimidazoleacetic acid)

COMPND    HMDB0002820
HETATM    1  C1  UNL     1      -2.883   0.727  -0.080  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.634  -0.038  -0.089  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.502  -1.337   0.179  1.00  0.00           C  
HETATM    4  N2  UNL     1      -0.195  -1.645   0.054  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.473  -0.539  -0.291  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.926  -0.451  -0.557  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.640  -0.193   0.713  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.760  -1.026   1.654  1.00  0.00           O  
HETATM    9  O2  UNL     1       3.242   1.050   0.923  1.00  0.00           O  
HETATM   10  C6  UNL     1      -0.436   0.479  -0.380  1.00  0.00           C  
HETATM   11  H1  UNL     1      -2.792   1.642  -0.701  1.00  0.00           H  
HETATM   12  H2  UNL     1      -3.145   1.007   0.941  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.699   0.086  -0.515  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.306  -2.011   0.459  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.127   0.405  -1.260  1.00  0.00           H  
HETATM   16  H6  UNL     1       2.345  -1.360  -1.093  1.00  0.00           H  
HETATM   17  H7  UNL     1       3.256   1.724   0.183  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.177   1.480  -0.643  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   10
CONECT    3    4    4   14
CONECT    4    5
CONECT    5    6   10   10
CONECT    6    7   15   16
CONECT    7    8    8    9
CONECT    9   17
CONECT   10   18
END
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SMILES for HMDB0002820 (Methylimidazoleacetic acid)

CN1C=NC(CC(O)=O)=C1
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INCHI for HMDB0002820 (Methylimidazoleacetic acid)

InChI=1S/C6H8N2O2/c1-8-3-5(7-4-8)2-6(9)10/h3-4H,2H2,1H3,(H,9,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
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
Health effect
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial application
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
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Placenta
Pathways
Normal Concentrations
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)Not Available
General References

Enzymes

Enzyme Details
1. Aldehyde dehydrogenase, dimeric NADP-preferring
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
Enzyme Details
2. Aldehyde dehydrogenase family 1 member A3
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
Enzyme Details
3. Aldehyde dehydrogenase family 3 member B2
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
Enzyme Details
4. Aldehyde dehydrogenase family 3 member B1
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