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Showing metabocard for 4-Imidazolone-5-propionic acid (HMDB0001014)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:23 UTC
HMDB IDHMDB0001014
Secondary Accession Numbers
  • HMDB01014
Metabolite Identification
Common Name4-Imidazolone-5-propionic acid
Description4-Imidazolone-5-propionic acid, also known as 4-imidazolone-5-propanoate, 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. An imidazol-4-one having a 2-carboxyethyl substituent at the 5-position. 4-Imidazolone-5-propionic acid is a strong basic compound (based on its pKa). 4-Imidazolone-5-propionic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 4-imidazolone-5-propionic acid participates in a number of enzymatic reactions. In particular, 4-imidazolone-5-propionic acid can be converted into urocanic acid through its interaction with the enzyme urocanate hydratase. In addition, 4-imidazolone-5-propionic acid can be converted into formiminoglutamic acid through the action of the enzyme probable imidazolonepropionase. In humans, 4-imidazolone-5-propionic acid is involved in histidine metabolism.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001014 (4-Imidazolone-5-propionic acid)

  Mrv0541 02231218522D          

 11 11  0  0  0  0            999 V2000
    0.7716   -0.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6031    0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3192    0.5681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -0.7387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1493    0.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185    0.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5709    0.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    1.1736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2402   -0.1296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2172   -1.2603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  1  2  0  0  0  0
M  END
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3D MOL for HMDB0001014 (4-Imidazolone-5-propionic acid)

HMDB0001014
     RDKit          3D
4-Imidazolone-5-propionic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.2882    1.3669   -1.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0305    0.6832   -0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3065    1.2334   -0.1404 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -0.6010    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3009   -1.0840    0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6770   -0.1993    0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7664    1.1476    0.3371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9514    1.4921    0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8322    0.3903    0.1550 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744   -0.7062    0.6216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5381   -1.8507    0.8643 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1575    0.7595   -0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4372   -1.4113   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -0.5174    1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361   -2.1063    0.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469   -1.2660   -1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -0.1777    1.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640    2.4918   -0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8730    0.3552   -0.0379 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10  6  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
M  END
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3D SDF for HMDB0001014 (4-Imidazolone-5-propionic acid)

  Mrv0541 02231218522D          

 11 11  0  0  0  0            999 V2000
    0.7716   -0.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6031    0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3192    0.5681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -0.7387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1493    0.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185    0.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5709    0.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    1.1736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2402   -0.1296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2172   -1.2603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  1  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001014

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCC1N=CNC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8N2O3/c9-5(10)2-1-4-6(11)8-3-7-4/h3-4H,1-2H2,(H,9,10)(H,7,8,11)

> <INCHI_KEY>
HEXMLHKQVUFYME-UHFFFAOYSA-N

> <FORMULA>
C6H8N2O3

> <MOLECULAR_WEIGHT>
156.1393

> <EXACT_MASS>
156.053492132

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
14.268682823697091

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(5-oxo-4,5-dihydro-1H-imidazol-4-yl)propanoic acid

> <ALOGPS_LOGP>
-1.13

> <JCHEM_LOGP>
-1.9946775750845265

> <ALOGPS_LOGS>
-1.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.378191466977164

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5071820563418865

> <JCHEM_PKA_STRONGEST_BASIC>
4.690199178947197

> <JCHEM_POLAR_SURFACE_AREA>
78.75999999999999

> <JCHEM_REFRACTIVITY>
35.2203

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(5-oxo-1,4-dihydroimidazol-4-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001014 (4-Imidazolone-5-propionic acid)

HMDB0001014
     RDKit          3D
4-Imidazolone-5-propionic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.2882    1.3669   -1.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0305    0.6832   -0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3065    1.2334   -0.1404 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -0.6010    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3009   -1.0840    0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6770   -0.1993    0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7664    1.1476    0.3371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9514    1.4921    0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8322    0.3903    0.1550 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744   -0.7062    0.6216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5381   -1.8507    0.8643 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1575    0.7595   -0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4372   -1.4113   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -0.5174    1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361   -2.1063    0.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469   -1.2660   -1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -0.1777    1.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640    2.4918   -0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8730    0.3552   -0.0379 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10  6  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
M  END
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PDB for HMDB0001014 (4-Imidazolone-5-propionic acid)

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  C   UNK     0       1.440  -1.212   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.126   0.295   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.463   1.060   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       2.971  -1.379   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.603   0.026   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.279   0.927   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.528   0.027   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.932   0.659   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.087   2.191   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.182  -0.242   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.405  -2.353   0.000  0.00  0.00           O+0
CONECT    1    2    4   11                                                  
CONECT    2    1    3    6                                                  
CONECT    3    2    5                                                       
CONECT    4    1    5                                                       
CONECT    5    4    3                                                       
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0001014 (4-Imidazolone-5-propionic acid)

COMPND    HMDB0001014
HETATM    1  O1  UNL     1       1.288   1.367  -1.112  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.031   0.683  -0.389  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.307   1.233  -0.140  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.706  -0.601   0.208  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.301  -1.084   0.059  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.677  -0.199   0.746  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.766   1.148   0.337  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.951   1.492   0.006  1.00  0.00           C  
HETATM    9  N2  UNL     1      -2.832   0.390   0.155  1.00  0.00           N  
HETATM   10  C6  UNL     1      -2.074  -0.706   0.622  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.538  -1.851   0.864  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.157   0.760  -0.417  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.437  -1.411  -0.135  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.959  -0.517   1.319  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.236  -2.106   0.537  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.047  -1.266  -1.009  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.493  -0.178   1.866  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.264   2.492  -0.345  1.00  0.00           H  
HETATM   19  H8  UNL     1      -3.873   0.355  -0.038  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6   15   16
CONECT    6    7   10   17
CONECT    7    8    8
CONECT    8    9   18
CONECT    9   10   19
CONECT   10   11   11
END
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SMILES for HMDB0001014 (4-Imidazolone-5-propionic acid)

OC(=O)CCC1N=CNC1=O
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INCHI for HMDB0001014 (4-Imidazolone-5-propionic acid)

InChI=1S/C6H8N2O3/c9-5(10)2-1-4-6(11)8-3-7-4/h3-4H,1-2H2,(H,9,10)(H,7,8,11)
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC6H8N2O3
Average Molecular Weight156.1393
Monoisotopic Molecular Weight156.053492132
IUPAC Name3-(5-oxo-4,5-dihydro-1H-imidazol-4-yl)propanoic acid
Traditional Name3-(5-oxo-1,4-dihydroimidazol-4-yl)propanoic acid
CAS Registry Number17340-16-8
SMILES
OC(=O)CCC1N=CNC1=O
InChI Identifier
InChI=1S/C6H8N2O3/c9-5(10)2-1-4-6(11)8-3-7-4/h3-4H,1-2H2,(H,9,10)(H,7,8,11)
InChI KeyHEXMLHKQVUFYME-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
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
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
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
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 IDFDB022371
KNApSAcK IDNot Available
Chemspider ID125
KEGG Compound IDC03680
BioCyc IDNot Available
BiGG ID42318
Wikipedia LinkImidazol-4-one-5-propionic acid
METLIN ID319
PubChem Compound128
PDB IDNot Available
ChEBI ID27384
Food Biomarker OntologyNot Available
VMH ID4IZP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Niederwieser A, Matasovic A, Steinmann B, Baerlocher K, Kempken B: Hydantoin-5-propionic aciduria in folic acid nondependent formiminoglutamic aciduria observed in two siblings. Pediatr Res. 1976 Apr;10(4):215-9. [PubMed:1272625 ]

Enzymes

Enzyme Details
1. Urocanate hydratase
General function:
Involved in urocanate hydratase activity
Specific function:
Not Available
Gene Name:
UROC1
Uniprot ID:
Q96N76
Molecular weight:
80911.275
Reactions
4-Imidazolone-5-propionic acid → Urocanic acid + Waterdetails
Enzyme Details
2. Probable imidazolonepropionase
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in cyclic amides
Specific function:
Not Available
Gene Name:
AMDHD1
Uniprot ID:
Q96NU7
Molecular weight:
46742.505
Reactions
4-Imidazolone-5-propionic acid + Water → Formiminoglutamic acid + Hydrogen Iondetails
4-Imidazolone-5-propionic acid + Water → Formiminoglutamic aciddetails