Showing metabocard for Imidazoleacetic acid (MMDBc0000403)

Plant
Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:36:58 UTC
Update Date2022-08-31 06:06:50 UTC
Metabolite IDMMDBc0000403
Metabolite Identification
Common NameImidazoleacetic acid
DescriptionImidazol-4-ylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by an imidazol-4-yl group. It has a role as a mouse metabolite. It is a monocarboxylic acid and a member of imidazoles. It derives from an acetic acid. It is a conjugate acid of an imidazol-4-ylacetate. It is a tautomer of an imidazol-5-ylacetic acid and a 2H-imidazol-4-ylacetic acid. Imidazoleacetic acid, also known as 4(5)-imidazoleacetate or IAA, 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. Imidazoleacetic acid exists in all living organisms, ranging from bacteria to humans. imidazoleacetic acid can be biosynthesized from imidazole-4-acetaldehyde through its interaction with the enzyme aldehyde dehydrogenase, mitochondrial. In humans, imidazoleacetic acid is involved in histidine metabolism. Outside of the human body, Imidazoleacetic acid has been detected, but not quantified in several different foods, such as chinese cinnamons, jostaberries, vanilla, butternut squash, and red rices. Imidazoleacetic acid is a potentially toxic compound. Imidazoleacetic acid is a metabolite product of Histamine metabolism.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000560be21a2590>


  Mrv1652305271900162D          

  9  9  0  0  0  0            999 V2000
   19.3428   -4.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3866   -3.0196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4930   -4.6085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0805   -3.3391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1604   -4.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9451   -4.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9055   -3.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8255   -4.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5581   -3.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  9  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000560be21a2590>

HMDB0002024
     RDKit          3D
Imidazoleacetic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.1351    0.7461   -1.4990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9127    0.0057   -0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810   -1.2315   -0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9874    0.5283    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4225    0.3208    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0925    1.0180   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3360    0.4868   -0.9258 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186   -0.5171   -0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2626   -0.6398    0.6329 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7052   -1.7410    0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1798   -0.0335    1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1159    1.6203    0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033    1.8358   -1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3145   -1.1320    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9672   -1.2672    1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  6 13  1  0
  8 14  1  0
  9 15  1  0
M  END
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3D SDF for #<Metabolite:0x0000560be21a2590>


  Mrv1652305271900162D          

  9  9  0  0  0  0            999 V2000
   19.3428   -4.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3866   -3.0196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4930   -4.6085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0805   -3.3391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1604   -4.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9451   -4.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9055   -3.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8255   -4.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5581   -3.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000403

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CC1=CN=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C5H6N2O2/c8-5(9)1-4-2-6-3-7-4/h2-3H,1H2,(H,6,7)(H,8,9)

> <INCHI_KEY>
PRJKNHOMHKJCEJ-UHFFFAOYSA-N

> <FORMULA>
C5H6N2O2

> <MOLECULAR_WEIGHT>
126.1133

> <EXACT_MASS>
126.042927446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.472699109880597

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(1H-imidazol-5-yl)acetic acid

> <ALOGPS_LOGP>
-0.50

> <JCHEM_LOGP>
-1.3990613301983859

> <ALOGPS_LOGS>
-0.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.995890284546483

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6538030747064596

> <JCHEM_PKA_STRONGEST_BASIC>
6.776708441179222

> <JCHEM_POLAR_SURFACE_AREA>
65.97999999999999

> <JCHEM_REFRACTIVITY>
30.197899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.33e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
IMAC

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x0000560be21a2590>

HMDB0002024
     RDKit          3D
Imidazoleacetic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.1351    0.7461   -1.4990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9127    0.0057   -0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810   -1.2315   -0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9874    0.5283    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4225    0.3208    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0925    1.0180   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3360    0.4868   -0.9258 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186   -0.5171   -0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2626   -0.6398    0.6329 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7052   -1.7410    0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1798   -0.0335    1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1159    1.6203    0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033    1.8358   -1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3145   -1.1320    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9672   -1.2672    1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  6 13  1  0
  8 14  1  0
  9 15  1  0
M  END
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PDB for #<Metabolite:0x0000560be21a2590>

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      36.107  -7.619   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      34.322  -5.637   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      30.787  -8.603   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      30.017  -6.233   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      32.033  -7.697   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.498  -8.173   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.557  -6.233   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.541  -7.697   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.642  -7.143   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    5    8                                                       
CONECT    4    7    8                                                       
CONECT    5    3    6    7                                                  
CONECT    6    5    9                                                       
CONECT    7    4    5                                                       
CONECT    8    3    4                                                       
CONECT    9    1    2    6                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for #<Metabolite:0x0000560be21a2590>

COMPND    HMDB0002024
HETATM    1  O1  UNL     1      -2.135   0.746  -1.499  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.913   0.006  -0.483  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.481  -1.231  -0.349  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.987   0.528   0.564  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.423   0.321   0.107  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.092   1.018  -0.861  1.00  0.00           C  
HETATM    7  N1  UNL     1       2.336   0.487  -0.926  1.00  0.00           N  
HETATM    8  C5  UNL     1       2.419  -0.517  -0.016  1.00  0.00           C  
HETATM    9  N2  UNL     1       1.263  -0.640   0.633  1.00  0.00           N  
HETATM   10  H1  UNL     1      -2.705  -1.741   0.509  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.180  -0.033   1.488  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.116   1.620   0.744  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.703   1.836  -1.476  1.00  0.00           H  
HETATM   14  H5  UNL     1       3.314  -1.132   0.178  1.00  0.00           H  
HETATM   15  H6  UNL     1       0.967  -1.267   1.387  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5   11   12
CONECT    5    6    6    9
CONECT    6    7   13
CONECT    7    8    8
CONECT    8    9   14
CONECT    9   15
END
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SMILES for #<Metabolite:0x0000560be21a2590>

OC(=O)CC1=CN=CN1
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INCHI for #<Metabolite:0x0000560be21a2590>

InChI=1S/C5H6N2O2/c8-5(9)1-4-2-6-3-7-4/h2-3H,1H2,(H,6,7)(H,8,9)
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Synonyms
ValueSource
1H-Imidazole-4-acetic acidChEBI
4(5)-ImidazoleacetateChEBI
4-ImidazoleacetateChEBI
Imidazole-4-acetateChEBI
1H-Imidazole-4-acetateGenerator
4(5)-Imidazoleacetic acidGenerator
4-Imidazoleacetic acidGenerator
Imidazole-4-acetic acidGenerator
ImidazoleacetateGenerator
1H-Imidazol-4-ylacetic acidHMDB
IAAHMDB
IMACHMDB
Imidazol-4-ylacetateHMDB
Imidazol-4-ylacetic acidHMDB
Imidazole acetateHMDB
Imidazolyl-4-acetic acidHMDB
IZCHMDB
Lopac-I-0375HMDB
Imidazole-4-acetic acid, sodium saltHMDB
Imidazole-4-acetic acid hydrochlorideHMDB
Molecular FormulaC5H6N2O2
Average Mass126.1133
Monoisotopic Mass126.042927446
IUPAC Name2-(1H-imidazol-5-yl)acetic acid
Traditional NameIMAC
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=CN=CN1
InChI Identifier
InChI=1S/C5H6N2O2/c8-5(9)1-4-2-6-3-7-4/h2-3H,1H2,(H,6,7)(H,8,9)
InChI KeyPRJKNHOMHKJCEJ-UHFFFAOYSA-N