Showing metabocard for 4-Imidazolone-5-propionic acid (MMDBc0047916)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:14:58 UTC
Update Date2024-04-30 20:32:28 UTC
Metabolite IDMMDBc0047916
Metabolite Identification
Common Name4-Imidazolone-5-propionic acid
Description4-Imidazolone-5-propanoate is a metabolite of histidine metabolism. It is produced from urocanic acid by the enzyme urocanate hydratase [EC:4.2.1.49]. 4-Imidazolone-5-propionic acid can spontaneously decay to 4-oxoglutaramate or formylisoglutamine. It is also converted to N-forminimo-L-glutamate by the enzyme imidazolonepropionase [EC:3.5.2.7].
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f46e4541be0>


  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 #<Metabolite:0x00007f46e4541be0>

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 #<Metabolite:0x00007f46e4541be0>


  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>
MMDBc0047916

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007f46e4541be0>

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 #<Metabolite:0x00007f46e4541be0>

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 #<Metabolite:0x00007f46e4541be0>

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 #<Metabolite:0x00007f46e4541be0>

OC(=O)CCC1N=CNC1=O
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INCHI for #<Metabolite:0x00007f46e4541be0>

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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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
Molecular FormulaC6H8N2O3
Average Mass156.1393
Monoisotopic Mass156.053492132
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