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Showing metabocard for Methylimidazole acetaldehyde (HMDB0004181)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 13:42:26 UTC
Update Date2023-02-21 17:16:57 UTC
HMDB IDHMDB0004181
Secondary Accession Numbers
  • HMDB04181
Metabolite Identification
Common NameMethylimidazole acetaldehyde
DescriptionMethylimidazole acetaldehyde belongs to the class of organic compounds known as n-substituted imidazoles. These are heterocyclic compounds containing an imidazole ring substituted at position 1. Methylimidazole acetaldehyde is a very strong basic compound (based on its pKa). Methylimidazole acetaldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, methylimidazole acetaldehyde participates in a number of enzymatic reactions. In particular, methylimidazole acetaldehyde can be biosynthesized from 1-methylhistamine through its interaction with the enzyme amine oxidase [flavin-containing] a. In addition, methylimidazole acetaldehyde can be converted into methylimidazoleacetic acid through the action of the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In humans, methylimidazole acetaldehyde is involved in histidine metabolism.
Structure
Data?1676999817
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004181 (Methylimidazole acetaldehyde)

  Mrv0541 02231219542D          

  9  9  0  0  0  0            999 V2000
   12.3278   -2.4485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5865   -5.2255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1739   -3.9559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4839   -3.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5865   -6.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1484   -2.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9990   -3.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9190   -4.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2539   -4.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  5  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
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3D MOL for HMDB0004181 (Methylimidazole acetaldehyde)

HMDB0004181
     RDKit          3D
Methylimidazole acetaldehyde
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.8273    0.1646   -0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4412   -0.1804    0.1990 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9563   -0.7706    1.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3833   -0.9032    1.1811 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7701   -0.3860   -0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1578   -0.3204   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8502    0.8765    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0647    0.8999    1.2131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3854    0.0554   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8436    1.1456   -0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3271   -0.5936   -0.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3614    0.2282    0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5877   -1.0821    2.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7157   -1.2525   -0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860   -0.1389   -1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1682    1.7230   -0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4660    0.5344   -1.5834 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
  5  9  2  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  6 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
M  END
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3D SDF for HMDB0004181 (Methylimidazole acetaldehyde)

  Mrv0541 02231219542D          

  9  9  0  0  0  0            999 V2000
   12.3278   -2.4485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5865   -5.2255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1739   -3.9559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4839   -3.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5865   -6.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1484   -2.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9990   -3.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9190   -4.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2539   -4.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  5  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004181

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C=NC(CC=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H8N2O/c1-8-4-6(2-3-9)7-5-8/h3-5H,2H2,1H3

> <INCHI_KEY>
GCQHUBANENYTLB-UHFFFAOYSA-N

> <FORMULA>
C6H8N2O

> <MOLECULAR_WEIGHT>
124.1405

> <EXACT_MASS>
124.063662888

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
12.788513676165564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
-0.056565778666666795

> <ALOGPS_LOGS>
-1.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.329154944715288

> <JCHEM_PKA_STRONGEST_BASIC>
6.2757724035193005

> <JCHEM_POLAR_SURFACE_AREA>
34.89

> <JCHEM_REFRACTIVITY>
33.9197

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylimidazole acetaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0004181 (Methylimidazole acetaldehyde)

HMDB0004181
     RDKit          3D
Methylimidazole acetaldehyde
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.8273    0.1646   -0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4412   -0.1804    0.1990 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9563   -0.7706    1.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3833   -0.9032    1.1811 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7701   -0.3860   -0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1578   -0.3204   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8502    0.8765    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0647    0.8999    1.2131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3854    0.0554   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8436    1.1456   -0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3271   -0.5936   -0.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3614    0.2282    0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5877   -1.0821    2.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7157   -1.2525   -0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860   -0.1389   -1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1682    1.7230   -0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4660    0.5344   -1.5834 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
  5  9  2  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  6 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
M  END
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PDB for HMDB0004181 (Methylimidazole acetaldehyde)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      23.012  -4.571   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      23.495  -9.754   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      22.725  -7.384   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      25.170  -6.138   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.495 -11.294   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.544  -4.731   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.265  -7.384   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.249  -8.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.741  -8.849   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    5    8    9                                                  
CONECT    3    7    8                                                       
CONECT    4    6    7                                                       
CONECT    5    2                                                            
CONECT    6    1    4                                                       
CONECT    7    3    4    9                                                  
CONECT    8    2    3                                                       
CONECT    9    2    7                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0004181 (Methylimidazole acetaldehyde)

COMPND    HMDB0004181
HETATM    1  C1  UNL     1      -2.827   0.165  -0.124  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.441  -0.180   0.199  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.956  -0.771   1.299  1.00  0.00           C  
HETATM    4  N2  UNL     1       0.383  -0.903   1.181  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.770  -0.386  -0.020  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.158  -0.320  -0.562  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.850   0.876   0.018  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.065   0.900   1.213  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.385   0.055  -0.607  1.00  0.00           C  
HETATM   10  H1  UNL     1      -2.844   1.146  -0.646  1.00  0.00           H  
HETATM   11  H2  UNL     1      -3.327  -0.594  -0.719  1.00  0.00           H  
HETATM   12  H3  UNL     1      -3.361   0.228   0.866  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.588  -1.082   2.120  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.716  -1.253  -0.405  1.00  0.00           H  
HETATM   15  H6  UNL     1       2.086  -0.139  -1.666  1.00  0.00           H  
HETATM   16  H7  UNL     1       3.168   1.723  -0.564  1.00  0.00           H  
HETATM   17  H8  UNL     1      -0.466   0.534  -1.583  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    9
CONECT    3    4    4   13
CONECT    4    5
CONECT    5    6    9    9
CONECT    6    7   14   15
CONECT    7    8    8   16
CONECT    9   17
END
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SMILES for HMDB0004181 (Methylimidazole acetaldehyde)

CN1C=NC(CC=O)=C1
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INCHI for HMDB0004181 (Methylimidazole acetaldehyde)

InChI=1S/C6H8N2O/c1-8-4-6(2-3-9)7-5-8/h3-5H,2H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
MethylimidazoleacetaldehydeChEBI
1-Methylimidazole-4-acetaldehydeKegg
1-Methylimidazol-3-ylacetaldehydeHMDB
N-Methylimidazole-3-acetaldehydeHMDB
Chemical FormulaC6H8N2O
Average Molecular Weight124.1405
Monoisotopic Molecular Weight124.063662888
IUPAC Name2-(1-methyl-1H-imidazol-4-yl)acetaldehyde
Traditional Namemethylimidazole acetaldehyde
CAS Registry Number19639-03-3
SMILES
CN1C=NC(CC=O)=C1
InChI Identifier
InChI=1S/C6H8N2O/c1-8-4-6(2-3-9)7-5-8/h3-5H,2H2,1H3
InChI KeyGCQHUBANENYTLB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-substituted imidazoles. These are heterocyclic compounds containing an imidazole ring substituted at position 1.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentN-substituted imidazoles
Alternative Parents
Substituents
  • N-substituted imidazole
  • Heteroaromatic compound
  • Alpha-hydrogen aldehyde
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.067Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023327
KNApSAcK IDNot Available
Chemspider ID167957
KEGG Compound IDC05827
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound193545
PDB IDNot Available
ChEBI ID28104
Food Biomarker OntologyNot Available
VMH ID3MLDZ
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zimatkin SM, Anichtchik OV: Alcohol-histamine interactions. Alcohol Alcohol. 1999 Mar-Apr;34(2):141-7. [PubMed:10344773 ]

Enzymes

Enzyme Details
1. Amine oxidase [flavin-containing] B
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
1-Methylhistamine + Water + Oxygen → Methylimidazole acetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
2. Amine oxidase [flavin-containing] A
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
1-Methylhistamine + Water + Oxygen → Methylimidazole acetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
3. 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
4. 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
5. 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
6. 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