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

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enzymes (2) Show 2 proteins
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
Data?1676999723
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
Download

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
Download

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

$$$$
Download

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
ValueSource
4,5-Dihydro-4-oxo-5-imidazolepropanoateChEBI
4,5-Dihydro-5-oxo-1H-imidazole-4-propanoic acidChEBI
4-Imidazolone-5-propanoateChEBI
Imidazol-4-one-5-propionic acidChEBI
4,5-Dihydro-4-oxo-5-imidazolepropanoic acidGenerator
4,5-Dihydro-5-oxo-1H-imidazole-4-propanoateGenerator
4-Imidazolone-5-propanoic acidGenerator
Imidazol-4-one-5-propionateGenerator
4-Imidazolone-5-propionateGenerator
(S)-3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoateHMDB
(S)-3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoic acidHMDB
3-(4-oxo-4,5-Dihydro-1H-imidazol-5-yl)propanoateHMDB
3-(4-oxo-4,5-Dihydro-1H-imidazol-5-yl)propanoic acidHMDB
3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoateHMDB
3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoic acidHMDB
Imidazolone propionateHMDB
Imidazolone propionic acidHMDB
ImidazolonepropanoateHMDB
Imidazolonepropanoic acidHMDB
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
PropertyValueSource
Water Solubility10.4 g/LALOGPS
logP-1.1ALOGPS
logP-2ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.51ChemAxon
pKa (Strongest Basic)4.69ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.22 m³·mol⁻¹ChemAxon
Polarizability14.27 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]+134.27831661259
DarkChem[M+H]+134.27831661259
DarkChem[M-H]-129.55831661259
DarkChem[M-H]-129.55831661259
AllCCS[M+H]+133.80732859911
AllCCS[M-H]-128.932859911
DeepCCS[M+H]+123.17430932474
DeepCCS[M-H]-119.45530932474
DeepCCS[M-2H]-156.29630932474
DeepCCS[M+Na]+131.73330932474
AllCCS[M+H]+133.832859911
AllCCS[M+H-H2O]+129.532859911
AllCCS[M+NH4]+137.932859911
AllCCS[M+Na]+139.032859911
AllCCS[M-H]-128.932859911
AllCCS[M+Na-2H]-130.232859911
AllCCS[M+HCOO]-131.732859911

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, 2022.0.83 minutes32390414
Predicted by Siyang on May 30, 20229.0164 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20226.78 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid111.6 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1071.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid298.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid82.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid182.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid66.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid243.0 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 Acid296.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)130.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid635.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid185.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid882.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid199.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid188.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate597.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA206.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water266.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Imidazolone-5-propionic acidOC(=O)CCC1N=CNC1=O2666.1Standard polar33892256
4-Imidazolone-5-propionic acidOC(=O)CCC1N=CNC1=O1511.2Standard non polar33892256
4-Imidazolone-5-propionic acidOC(=O)CCC1N=CNC1=O1710.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Imidazolone-5-propionic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCC1N=CNC1=O1747.7Semi standard non polar33892256
4-Imidazolone-5-propionic acid,1TMS,isomer #2C[Si](C)(C)N1C=NC(CCC(=O)O)C1=O1781.1Semi standard non polar33892256
4-Imidazolone-5-propionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1N=CN([Si](C)(C)C)C1=O1826.2Semi standard non polar33892256
4-Imidazolone-5-propionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1N=CN([Si](C)(C)C)C1=O1837.5Standard non polar33892256
4-Imidazolone-5-propionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1N=CN([Si](C)(C)C)C1=O2768.3Standard polar33892256
4-Imidazolone-5-propionic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1N=CNC1=O1972.9Semi standard non polar33892256
4-Imidazolone-5-propionic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC(CCC(=O)O)C1=O2037.8Semi standard non polar33892256
4-Imidazolone-5-propionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1N=CN([Si](C)(C)C(C)(C)C)C1=O2318.4Semi standard non polar33892256
4-Imidazolone-5-propionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1N=CN([Si](C)(C)C(C)(C)C)C1=O2259.0Standard non polar33892256
4-Imidazolone-5-propionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1N=CN([Si](C)(C)C(C)(C)C)C1=O2935.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Imidazolone-5-propionic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ec-9500000000-a11c5ca5f02078a53fc72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Imidazolone-5-propionic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8920000000-fed80cbe61ee26d1486a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Imidazolone-5-propionic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 10V, Positive-QTOFsplash10-000i-0900000000-36ccc12772d3e7b3bc012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 20V, Positive-QTOFsplash10-01p9-0900000000-8c7ad9614b1acbee7f962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 40V, Positive-QTOFsplash10-0f6x-9000000000-0561b28120ae734b99cf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 10V, Negative-QTOFsplash10-0a4i-0900000000-d24b3a3769f74c7e18582017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 20V, Negative-QTOFsplash10-0a4u-8900000000-98a3f029124c94f1e6b12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 40V, Negative-QTOFsplash10-0006-9100000000-c75d14d5396894fff6f52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 10V, Negative-QTOFsplash10-0a4i-0900000000-c39bbd8fcbd13dc72dd12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 20V, Negative-QTOFsplash10-08gl-8900000000-9ecbb63abc1319562a122021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 40V, Negative-QTOFsplash10-000x-9000000000-50c3ee9255335f634b302021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 10V, Positive-QTOFsplash10-0bt9-0900000000-75e80efea901b323015e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 20V, Positive-QTOFsplash10-03di-6900000000-a2d551ead7379a1c56b72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 40V, Positive-QTOFsplash10-0006-9100000000-d2613558e32279e944b32021-09-25Wishart 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 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