Showing metabocard for Imidazolepropionic acid (MMDBc0000412)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:37:11 UTC
Update Date2024-04-30 19:32:18 UTC
Metabolite IDMMDBc0000412
Metabolite Identification
Common NameImidazolepropionic acid
DescriptionImidazolepropionic acid, also known as deaminohistidine or 4-imidazolylpropionate (ImP), 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. ImP is a metabolite of histidine and it is formed from histidine via a urocanate intermediate in gut microbiota by the enzyme urocanate reductase (urdA). ImP is a very strong basic compound (based on its pKa). ImP is a product of histidine metabolism which may involve oxidation or transamination. This compound is found in the urine of rats loaded with histidine (PMID: 6021220 ). ImP (100 µM) decreases protein levels of insulin receptor substrate 1 (IRS-1), IRS-2, and phosphorylated Akt and increases levels of the mTORC1 activation marker phosphorylated p70 ribosomal S6 kinase enzyme (p70S6K) in primary mouse hepatocytes. It induces deficits in glucose tolerance in germ-free and conventionally raised mice when administered at doses of 500 and 100 µg/animal, respectively. It has also been found to prevent reductions in blood glucose levels induced by Metformin - a first-line therapy for type 2 diabetes - in mice (PMID: 33208748 , PMID: 32783890 , PMID: 30401435 ). Microbiota-host-diet interactions are known to contribute to the development of metabolic diseases and ImP is a known such microbially produced metabolic derivative histidine that impairs the mechanism of glucose. Specifically, ImP is found to be elevated in serum of individuals with pre-diabetes and diabetes (PMID: 33208748 ). Those with type 2 diabetes are shown to have significantly increased levels of serum ImP [0.028 μM (0.016–0.059) median and interquartile range; n = 140] compared to subjects with prediabetes [0.028 μM (0.017–0.049) median and interquartile range; n = 654] or normal glucose tolerance [0.020 μM (0.013–0.033) median and interquartile range; n = 359] (PMID: 33208748 ). ImP is also found to be elevated in serum of individuals with cardiovascular disease (CVD) (PMID: 33208748 ). ImP levels were significantly increased in CVD individuals [0.037 μM (0.021–0.069) median and interquartile range; n = 390] compared to individuals without CVD [0.025 μM (0.015–0.048) median and interquartile range; n = 1568] (P < 0.001, linear regression after adjustment for age, gender, BMI, ethnicity, diabetes status, and creatinine clearance) (PMID: 33208748 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdafcc942d8>


  Mrv1652311041919122D          

 10 10  0  0  0  0            999 V2000
 9999.978410000.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6931 9999.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.409210000.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1253 9999.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.409210000.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.590710000.2517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9233 9999.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1782 9998.9821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0032 9998.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2581 9999.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  9 10  2  0  0  0  0
  6  7  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1 10  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fdafcc942d8>

HMDB0002271
     RDKit          3D
Imidazolepropionic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
   -1.0924    0.7055   -1.6023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829   -0.0495   -1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392    0.1890   -1.1453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4189   -1.1738   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4068   -0.7141    0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8137   -0.1054    0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0810    1.2206   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144    1.3586   -0.5345 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250    0.1286   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9503   -0.7693   -0.1235 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8073    0.4499   -0.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735   -1.6673    0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0018   -2.0118   -0.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8511   -0.0456    1.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613   -1.6093    1.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4209    2.0630    0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    2.2198   -0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8039   -0.1887   -0.9520 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
M  END
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3D SDF for #<Metabolite:0x00007fdafcc942d8>


  Mrv1652311041919122D          

 10 10  0  0  0  0            999 V2000
 9999.978410000.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6931 9999.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.409210000.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1253 9999.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.409210000.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.590710000.2517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9233 9999.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1782 9998.9821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0032 9998.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2581 9999.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  9 10  2  0  0  0  0
  6  7  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000412

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CCC1=CNC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10)

> <INCHI_KEY>
ZCKYOWGFRHAZIQ-UHFFFAOYSA-N

> <FORMULA>
C6H8N2O2

> <MOLECULAR_WEIGHT>
140.1399

> <EXACT_MASS>
140.05857751

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.59353142060863

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-0.09

> <JCHEM_LOGP>
-1.0927005043754943

> <ALOGPS_LOGS>
-0.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.975907586137506

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.035312219151665

> <JCHEM_PKA_STRONGEST_BASIC>
6.7653984265305445

> <JCHEM_POLAR_SURFACE_AREA>
65.98

> <JCHEM_REFRACTIVITY>
34.9529

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.59e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-imidazolepropionic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fdafcc942d8>

HMDB0002271
     RDKit          3D
Imidazolepropionic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
   -1.0924    0.7055   -1.6023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829   -0.0495   -1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392    0.1890   -1.1453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4189   -1.1738   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4068   -0.7141    0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8137   -0.1054    0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0810    1.2206   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144    1.3586   -0.5345 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250    0.1286   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9503   -0.7693   -0.1235 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8073    0.4499   -0.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735   -1.6673    0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0018   -2.0118   -0.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8511   -0.0456    1.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613   -1.6093    1.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4209    2.0630    0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    2.2198   -0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8039   -0.1887   -0.9520 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
M  END
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PDB for #<Metabolite:0x00007fdafcc942d8>

HEADER    PROTEIN                                 04-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-NOV-19         0                                  
HETATM    1  C   UNK     0    8666.6268666.983   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.9608666.214   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.2978666.983   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8670.6348666.214   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8669.2978668.524   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0    8664.0368667.137   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    8662.7908666.231   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    8663.2668664.767   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    8664.8068664.767   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.2828666.231   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    7   10                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9   10    8                                                       
CONECT   10    9    6    1                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for #<Metabolite:0x00007fdafcc942d8>

COMPND    HMDB0002271
HETATM    1  O1  UNL     1      -1.092   0.706  -1.602  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.883  -0.049  -1.007  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.239   0.189  -1.145  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.419  -1.174  -0.167  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.407  -0.714   0.824  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.814  -0.105   0.257  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.081   1.221  -0.015  1.00  0.00           C  
HETATM    8  N1  UNL     1       2.314   1.359  -0.535  1.00  0.00           N  
HETATM    9  C6  UNL     1       2.825   0.129  -0.590  1.00  0.00           C  
HETATM   10  N2  UNL     1       1.950  -0.769  -0.124  1.00  0.00           N  
HETATM   11  H1  UNL     1      -3.807   0.450  -0.325  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.274  -1.667   0.346  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.002  -2.012  -0.820  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.851  -0.046   1.608  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.061  -1.609   1.418  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.421   2.063   0.156  1.00  0.00           H  
HETATM   17  H7  UNL     1       2.826   2.220  -0.849  1.00  0.00           H  
HETATM   18  H8  UNL     1       3.804  -0.189  -0.952  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5   12   13
CONECT    5    6   14   15
CONECT    6    7    7   10
CONECT    7    8   16
CONECT    8    9   17
CONECT    9   10   10   18
END
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SMILES for #<Metabolite:0x00007fdafcc942d8>

OC(=O)CCC1=CNC=N1
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INCHI for #<Metabolite:0x00007fdafcc942d8>

InChI=1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10)
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Synonyms
ValueSource
1H-Imidazole-4-propanoic acidChEBI
3-(1H-Imidazol-4-yl)propionic acidChEBI
3-(Imidazol-4-yl)propanoic acidChEBI
3-(Imidazol-4-yl)propionic acidChEBI
4-Imidazolylpropanoic acidChEBI
4-Imidazolylpropionic acidChEBI
DeaminohistidineChEBI
Imidazolylpropionic acidChEBI
3-(1H-Imidazol-4-yl)propanoateKegg
1H-Imidazole-4-propanoateGenerator
3-(1H-Imidazol-4-yl)propionateGenerator
3-(Imidazol-4-yl)propanoateGenerator
3-(Imidazol-4-yl)propionateGenerator
4-ImidazolylpropanoateGenerator
4-ImidazolylpropionateGenerator
ImidazolylpropionateGenerator
3-(1H-Imidazol-4-yl)propanoic acidGenerator
ImidazolepropionateGenerator
3-(1H-Imidazol-4-yl)-propionateHMDB
3-(1H-Imidazol-4-yl)-propionic acidHMDB
5-ImidazolepropionateHMDB
5-Imidazolepropionic acidHMDB, MeSH
deamino-HistidineHMDB
UROHMDB
Imidazole propionateMeSH, HMDB
DihydrourocanateGenerator, HMDB
1H-Imidazole-4(5)-propanoateGenerator, HMDB
1H-Imidazole-4-propionic acidHMDB
3-(1H-4-Imidazolyl)propanoic acidHMDB
3-(1H-4-Imidazolyl)propionic acidHMDB
3-(4-Imidazolyl)propanoic acidHMDB
3-(4-Imidazolyl)propionic acidHMDB
3-(Imidazol-4(5)-yl)propanoic acidHMDB
3-(Imidazol-4(5)-yl)propionic acidHMDB
5-(2-Carboxyethyl) imidazoleHMDB
Dihydrourocanic acidHMDB
Dihydrourocanoic acidHMDB
Imidazole-4(5)-propanoic acidHMDB
Imidazole-4(5)-propionic acidHMDB
Imidazole-4-propanoic acidHMDB
Imidazole-4-propionic acidHMDB
Imidazolylpropanoic acidHMDB
beta-(5-Imidazolyl)propanoic acidHMDB
beta-(5-Imidazolyl)propionic acidHMDB
beta-Imidazolyl-4(5)-propanoic acidHMDB
beta-Imidazolyl-4(5)-propionic acidHMDB
β-(5-Imidazolyl)propanoic acidHMDB
β-(5-Imidazolyl)propionic acidHMDB
β-Imidazolyl-4(5)-propanoic acidHMDB
β-Imidazolyl-4(5)-propionic acidHMDB
Molecular FormulaC6H8N2O2
Average Mass140.1399
Monoisotopic Mass140.05857751
IUPAC Name3-(1H-imidazol-5-yl)propanoic acid
Traditional Name5-imidazolepropionic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCC1=CNC=N1
InChI Identifier
InChI=1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10)
InChI KeyZCKYOWGFRHAZIQ-UHFFFAOYSA-N