Showing metabocard for Methylimidazoleacetic acid (MMDBc0000818)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 22:03:42 UTC
Update Date2022-08-31 06:16:53 UTC
Metabolite IDMMDBc0000818
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000560be22df3e0>


  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 #<Metabolite:0x0000560be22df3e0>

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 #<Metabolite:0x0000560be22df3e0>


  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>
MMDBc0000818

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x0000560be22df3e0>

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 #<Metabolite:0x0000560be22df3e0>

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 #<Metabolite:0x0000560be22df3e0>

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 #<Metabolite:0x0000560be22df3e0>

CN1C=NC(CC(O)=O)=C1
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INCHI for #<Metabolite:0x0000560be22df3e0>

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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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
Molecular FormulaC6H8N2O2
Average Mass140.1399
Monoisotopic Mass140.05857751
IUPAC Name2-(1-methyl-1H-imidazol-4-yl)acetic acid
Traditional Namemethylimidazoleacetic acid
CAS Registry NumberNot Available
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