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Showing metabocard for Imidazolepropionic acid (HMDB0002271)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:45 UTC
Update Date2023-02-21 17:16:18 UTC
HMDB IDHMDB0002271
Secondary Accession Numbers
  • HMDB02271
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
Data?1676999778
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002271 (Imidazolepropionic acid)


  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
Download

3D MOL for HMDB0002271 (Imidazolepropionic acid)

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
Download

3D SDF for HMDB0002271 (Imidazolepropionic acid)


  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>
HMDB0002271

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0002271 (Imidazolepropionic acid)

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 HMDB0002271 (Imidazolepropionic acid)

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 HMDB0002271 (Imidazolepropionic acid)

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 HMDB0002271 (Imidazolepropionic acid)

OC(=O)CCC1=CNC=N1
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INCHI for HMDB0002271 (Imidazolepropionic acid)

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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View in JSmolView NMR AssignmentsView Stereo Labels
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
Chemical FormulaC6H8N2O2
Average Molecular Weight140.1399
Monoisotopic Molecular Weight140.05857751
IUPAC Name3-(1H-imidazol-5-yl)propanoic acid
Traditional Name5-imidazolepropionic acid
CAS Registry Number1074-59-5
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
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
  • Heteroaromatic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point206 - 208 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility43.9 g/LALOGPS
logP-0.09ALOGPS
logP-1.1ChemAxon
logS-0.48ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)6.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.98 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.95 m³·mol⁻¹ChemAxon
Polarizability13.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+131.40431661259
DarkChem[M-H]-125.22231661259
DeepCCS[M+H]+126.67830932474
DeepCCS[M-H]-123.54530932474
DeepCCS[M-2H]-160.56830932474
DeepCCS[M+Na]+135.50230932474
AllCCS[M+H]+130.532859911
AllCCS[M+H-H2O]+126.032859911
AllCCS[M+NH4]+134.732859911
AllCCS[M+Na]+135.932859911
AllCCS[M-H]-127.332859911
AllCCS[M+Na-2H]-129.032859911
AllCCS[M+HCOO]-130.932859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.2 minutes32390414
Predicted by Siyang on May 30, 20228.4613 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.81 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid305.8 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid462.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid293.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid54.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid181.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid52.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid266.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid223.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)751.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid551.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid35.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid644.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid182.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid267.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate592.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA453.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water324.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Imidazolepropionic acidOC(=O)CCC1=CNC=N12714.5Standard polar33892256
Imidazolepropionic acidOC(=O)CCC1=CNC=N11348.4Standard non polar33892256
Imidazolepropionic acidOC(=O)CCC1=CNC=N11657.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Imidazolepropionic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCC1=C[NH]C=N11490.0Semi standard non polar33892256
Imidazolepropionic acid,1TMS,isomer #2C[Si](C)(C)N1C=NC(CCC(=O)O)=C11742.5Semi standard non polar33892256
Imidazolepropionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C=N11744.1Semi standard non polar33892256
Imidazolepropionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C=N11639.0Standard non polar33892256
Imidazolepropionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C)C=N11997.9Standard polar33892256
Imidazolepropionic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1=C[NH]C=N11726.6Semi standard non polar33892256
Imidazolepropionic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC(CCC(=O)O)=C12008.0Semi standard non polar33892256
Imidazolepropionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C=N12223.6Semi standard non polar33892256
Imidazolepropionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C=N12081.6Standard non polar33892256
Imidazolepropionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1=CN([Si](C)(C)C(C)(C)C)C=N12166.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Imidazolepropionic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000y-9200000000-8af7c94edf62d10d79052017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Imidazolepropionic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9200000000-466ffc1c8385b58116772017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Imidazolepropionic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Imidazolepropionic acid CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 20V, Positive-QTOFsplash10-0006-0900000000-593be5cf10aba06261f02019-03-07HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazolepropionic acid 10V, Positive-QTOFsplash10-006x-1900000000-f813e755bd0c33989b992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazolepropionic acid 20V, Positive-QTOFsplash10-006t-9700000000-fc60958d4ee5d49335ca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazolepropionic acid 40V, Positive-QTOFsplash10-0gb9-9000000000-c8f93079184c6ee4b5d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazolepropionic acid 10V, Negative-QTOFsplash10-000i-2900000000-684a7e6823977a73c2b42016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazolepropionic acid 20V, Negative-QTOFsplash10-000j-6900000000-3f4fc2398941bf5c73952016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazolepropionic acid 40V, Negative-QTOFsplash10-05mo-9100000000-49b8e29531a2099a80ce2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazolepropionic acid 10V, Negative-QTOFsplash10-000b-9400000000-f2cb4a7574ec2ba4ce922021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazolepropionic acid 20V, Negative-QTOFsplash10-014j-9100000000-8e37d715ddc9ef376bf72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazolepropionic acid 40V, Negative-QTOFsplash10-014l-9000000000-2ee2f80749be6e61f7572021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazolepropionic acid 10V, Positive-QTOFsplash10-00dl-5900000000-bb071711eca6657a6d912021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazolepropionic acid 20V, Positive-QTOFsplash10-0002-9100000000-4bbf16992517da7c64f62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazolepropionic acid 40V, Positive-QTOFsplash10-014l-9000000000-fe8160b6c4b3de352e442021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleSupragingival Plaque details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
  3. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Supragingival Plaque
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012461
KNApSAcK IDC00050820
Chemspider ID63798
KEGG Compound IDC20522
BioCyc IDCPD-15171
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6585
PubChem Compound70630
PDB IDNot Available
ChEBI ID73087
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAkabori, Shiro. Synthesis of imidazole derivatives from a-amino acids. I. A new synthesis of desaminohistidine and a contribution to the knowledge of the constitution of ergothioneine. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1933), 66B 151-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Block WD, Westhoff MH, Steele BF: Histidine metabolism in the human adult: histidine blood tolerance, and the effect of continued free L-histidine ingestion on the concentration of imidazole compounds in blood and urine. J Nutr. 1967 Feb;91(2):189-94. [PubMed:6021220 ]
  2. Antener I, Verwilghen AM, Van Geert C, Mauron J: Biochemical study of malnutrition. Part VI: Histidine and its metabolites. Int J Vitam Nutr Res. 1983;53(2):199-209. [PubMed:6136484 ]
  3. SEN NP, McGEER PL, PAUL RM: Imidazolepropionic acid as a urinary metabolite of L-histidine. Biochem Biophys Res Commun. 1962 Oct 17;9:257-61. [PubMed:13987921 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]