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Showing metabocard for Trans-urocanate (HMDB0062562)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-03-23 04:25:14 UTC
Update Date2022-03-07 03:17:56 UTC
HMDB IDHMDB0062562
Secondary Accession Numbers
  • HMDB62562
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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0062562 (Trans-urocanate)

  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 HMDB0062562 (Trans-urocanate)

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 HMDB0062562 (Trans-urocanate)

  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>
HMDB0062562

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0062562 (Trans-urocanate)

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 HMDB0062562 (Trans-urocanate)

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 HMDB0062562 (Trans-urocanate)

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 HMDB0062562 (Trans-urocanate)

OC(=O)C=CC1=CN=CN1
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INCHI for HMDB0062562 (Trans-urocanate)

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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View in JSmolView NMR AssignmentsView Stereo Labels
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
Chemical FormulaC6H6N2O2
Average Molecular Weight138.126
Monoisotopic Molecular Weight138.042927441
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
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 effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility255 g/lALOGPS
LogP-0.16ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 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)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleMissing teeth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  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 ]
Attachment loss
  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 ]
Missing teeth
  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 ]
Periodontal Probing Depth
  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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDUROCANATE
BiGG IDNot Available
Wikipedia LinkUrocanic_acid
METLIN IDNot Available
PubChem Compound1178
PDB IDNot Available
ChEBI ID27248
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available