Showing metabocard for Trans-urocanate (MMDBc0000697)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:52:58 UTC
Update Date2022-08-31 06:11:10 UTC
Metabolite IDMMDBc0000697
Metabolite Identification
Common NameTrans-urocanate
Descriptionurocanic acid, also known as urocanate, 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 alpha,beta-unsaturated monocarboxylic acid that is prop-2-enoic acid substituted by a 1H-imidazol-4-yl group at position 3. urocanic acid is a very strong basic compound (based on its pKa).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000556b6af7c8a0>


  Mrv1652305171806352D          

 10 10  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  8  1  4  0  0  0
  8  9  2  0  0  0  0
  7  3  1  0  0  0  0
 10  8  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000556b6af7c8a0>

HMDB0062562
     RDKit          3D
Trans-urocanate
 16 16  0  0  0  0  0  0  0  0999 V2000
    0.6947    2.3093   -0.5048 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5457    1.6984    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7273    2.4503    0.4944 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4807    0.3856    0.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669   -0.5682    0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6307   -0.7410    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601   -1.9480    0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5154   -1.8027   -0.5173 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5953   -0.5926   -1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269    0.0338   -0.6908 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5571    2.0865    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4369    0.1264    1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0392   -1.5045    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0451   -2.8183    0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3598   -0.1271   -1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    1.0120   -0.9746 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  2  3
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  6  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  7 14  1  0
  9 15  1  0
 10 16  1  0
M  END
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3D SDF for #<Metabolite:0x0000556b6af7c8a0>


  Mrv1652305171806352D          

 10 10  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  8  1  4  0  0  0
  8  9  2  0  0  0  0
  7  3  1  0  0  0  0
 10  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000697

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C=CC1=CN=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)

> <INCHI_KEY>
LOIYMIARKYCTBW-UHFFFAOYSA-N

> <FORMULA>
C6H6N2O2

> <MOLECULAR_WEIGHT>
138.126

> <EXACT_MASS>
138.042927441

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.797969341658671

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(1H-imidazol-5-yl)prop-2-enoic acid

> <ALOGPS_LOGP>
0.00

> <JCHEM_LOGP>
-0.8621971110634697

> <ALOGPS_LOGS>
-0.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.614937424603038

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9142938692938087

> <JCHEM_PKA_STRONGEST_BASIC>
6.825512252414499

> <JCHEM_POLAR_SURFACE_AREA>
65.98

> <JCHEM_REFRACTIVITY>
35.8922

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
urocanic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x0000556b6af7c8a0>

HMDB0062562
     RDKit          3D
Trans-urocanate
 16 16  0  0  0  0  0  0  0  0999 V2000
    0.6947    2.3093   -0.5048 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5457    1.6984    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7273    2.4503    0.4944 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4807    0.3856    0.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669   -0.5682    0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6307   -0.7410    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601   -1.9480    0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5154   -1.8027   -0.5173 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5953   -0.5926   -1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269    0.0338   -0.6908 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5571    2.0865    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4369    0.1264    1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0392   -1.5045    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0451   -2.8183    0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3598   -0.1271   -1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    1.0120   -0.9746 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  2  3
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  6  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  7 14  1  0
  9 15  1  0
 10 16  1  0
M  END
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PDB for #<Metabolite:0x0000556b6af7c8a0>

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.608   6.700   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.060   6.700   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    3                                                       
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for #<Metabolite:0x0000556b6af7c8a0>

COMPND    HMDB0062562
HETATM    1  O1  UNL     1       0.695   2.309  -0.505  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.546   1.698   0.183  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.727   2.450   0.494  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.481   0.386   0.678  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.667  -0.568   0.639  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.631  -0.741   0.035  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.360  -1.948   0.141  1.00  0.00           C  
HETATM    8  N1  UNL     1      -2.515  -1.803  -0.517  1.00  0.00           N  
HETATM    9  C6  UNL     1      -2.595  -0.593  -1.046  1.00  0.00           C  
HETATM   10  N2  UNL     1      -1.427   0.034  -0.691  1.00  0.00           N  
HETATM   11  H1  UNL     1       3.557   2.087   0.048  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.437   0.126   1.279  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.039  -1.505   1.210  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.045  -2.818   0.655  1.00  0.00           H  
HETATM   15  H5  UNL     1      -3.360  -0.127  -1.630  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.215   1.012  -0.975  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    5   12
CONECT    5    6   13
CONECT    6    7    7   10
CONECT    7    8   14
CONECT    8    9    9
CONECT    9   10   15
CONECT   10   16
END
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SMILES for #<Metabolite:0x0000556b6af7c8a0>

OC(=O)C=CC1=CN=CN1
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INCHI for #<Metabolite:0x0000556b6af7c8a0>

InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)
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Synonyms
ValueSource
3-(1H-Imidazol-4-yl)-2-propenoic acidChEBI
3-Imidazol-4-ylacrylic acidChEBI
3-(1H-Imidazol-4-yl)-2-propenoateGenerator
3-Imidazol-4-ylacrylateGenerator
UrocanateGenerator
trans-Urocanic acidGenerator
Molecular FormulaC6H6N2O2
Average Mass138.126
Monoisotopic Mass138.042927441
IUPAC Name3-(1H-imidazol-5-yl)prop-2-enoic acid
Traditional Nameurocanic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C=CC1=CN=CN1
InChI Identifier
InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)
InChI KeyLOIYMIARKYCTBW-UHFFFAOYSA-N