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Showing NP-Card for (E)-Urocanic acid (NP0336805)

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Record Information
Version2.0
Created at2024-09-11 07:53:49 UTC
Updated at2024-09-11 07:53:50 UTC
NP-MRD IDNP0336805
Secondary Accession NumbersNone
Natural Product Identification
Common Name(E)-Urocanic acid
Description(E)-Urocanic acid, also known as (e)-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 (E)-Urocanic acid is a very strong basic compound (based on its pKa). Outside of the human body, (E)-Urocanic acid has been detected, but not quantified in, mushrooms. This could make (e)-urocanic acid a potential biomarker for the consumption of these foods. A urocanic acid in which the double bond of the carboxyethene moiety has Z configuration.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336805 ((E)-Urocanic acid)


  Mrv1652307201900022D          

 12 12  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    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
    0.1553   -0.1553    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
   -0.8612    1.9393    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
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  5  1  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  1  1  0  0  0  0
 12  2  1  0  0  0  0
M  END
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3D MOL for NP0336805 ((E)-Urocanic acid)

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3D SDF for NP0336805 ((E)-Urocanic acid)

  Mrv1652307201900022D          

 12 12  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    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
    0.1553   -0.1553    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
   -0.8612    1.9393    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
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  5  1  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  1  1  0  0  0  0
 12  2  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(/[H])C1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1-

> <INCHI_KEY>
LOIYMIARKYCTBW-UPHRSURJSA-N

> <FORMULA>
C6H6N2O2

> <MOLECULAR_WEIGHT>
138.124

> <EXACT_MASS>
138.042927446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.748103416808775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.00

> <JCHEM_LOGP>
-0.8828181046975262

> <ALOGPS_LOGS>
-0.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.614937423045216

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.214868210898282

> <JCHEM_PKA_STRONGEST_BASIC>
6.824937912367848

> <JCHEM_POLAR_SURFACE_AREA>
65.98

> <JCHEM_REFRACTIVITY>
35.892199999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-(3H-imidazol-4-yl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0336805 ((E)-Urocanic acid)
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PDB for NP0336805 ((E)-Urocanic acid)
HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUL-19         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.608   3.620   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      -1.608   2.080   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.941   4.390   0.000  0.00  0.00           O+0
HETATM   11  H   UNK     0       2.393   4.390   0.000  0.00  0.00           H+0
HETATM   12  H   UNK     0      -0.274   5.930   0.000  0.00  0.00           H+0
CONECT    1    2    5   11                                                  
CONECT    2    1    6   12                                                  
CONECT    3    5    7                                                       
CONECT    4    7    8                                                       
CONECT    5    1    3    8                                                  
CONECT    6    2    9   10                                                  
CONECT    7    3    4                                                       
CONECT    8    4    5                                                       
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    1                                                            
CONECT   12    2                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0336805 ((E)-Urocanic acid)
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SMILES for NP0336805 ((E)-Urocanic acid)
[H]\C(=C(/[H])C1=CN=CN1)C(O)=O
Download
INCHI for NP0336805 ((E)-Urocanic acid)
InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1-
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Synonyms
ValueSource
(Z)-Imidazole-4-acrylic acidChEBI
(Z)-Imidazole-4-acrylateGenerator
(e)-UrocanateGenerator
(2E)-3-(1H-Imidazol-4-yl)acrylic acidHMDB
(2E)-3-(1H-Imidazol-4-yl)prop-2-enoic acidHMDB
(e)-3-(1H-Imidazol-4-yl)-2-propenoic acidHMDB
3-(1H-Imidazol-4-yl)-(e)-2-propenoic acidHMDB
3-(1H-Imidazol-4-yl)prop-2-enoic acidHMDB
3-(1H-Imidazol-5-yl)-2-propenoic acidHMDB
3-Imidazol-4-ylacrylic acidHMDB
cis-Urocanic acidHMDB
Imidazole-4-propene-2-enoic acidHMDB
trans-Urocanic acidHMDB
Urocanic acidHMDB
Urocanic acid, cisHMDB
Chemical FormulaC6H6N2O2
Average Mass138.1240 Da
Monoisotopic Mass138.04293 Da
IUPAC Name(2Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid
Traditional Name(2Z)-3-(3H-imidazol-4-yl)prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(=C(/[H])C1=CN=CN1)C(O)=O
InChI Identifier
InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1-
InChI KeyLOIYMIARKYCTBW-UPHRSURJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0ALOGPS
logP-0.88ChemAxon
logS-0.82ALOGPS
pKa (Strongest Acidic)3.21ChemAxon
pKa (Strongest Basic)6.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.98 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.89 m³·mol⁻¹ChemAxon
Polarizability12.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034174  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012465  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1549103  
PDB IDNot Available
ChEBI ID30818  
Good Scents IDNot Available
References
General ReferencesNot Available