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Showing NP-Card for Methylimidazoleacetic acid (NP0001030)

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Record Information
Version2.0
Created at2006-05-22 15:12:12 UTC
Updated at2020-11-24 22:20:15 UTC
NP-MRD IDNP0001030
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001030 (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 NP0001030 (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
Download

3D SDF for NP0001030 (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>
NP0001030

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0001030 (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 NP0001030 (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 NP0001030 (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 NP0001030 (Methylimidazoleacetic acid)

CN1C=NC(CC(O)=O)=C1
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INCHI for NP0001030 (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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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, hydrochlorideHMDB
Chemical FormulaC6H8N2O2
Average Mass140.1399 Da
Monoisotopic Mass140.05858 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002820
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]
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