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Showing NP-Card for 3-(3h-imidazol-4-yl)prop-2-enoic acid (NP0322164)

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Record Information
Version2.0
Created at2022-09-12 00:47:04 UTC
Updated at2022-09-12 00:47:04 UTC
NP-MRD IDNP0322164
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-(3h-imidazol-4-yl)prop-2-enoic acid
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. 3-(3h-imidazol-4-yl)prop-2-enoic acid is found in Coprinopsis atramentaria, Hippospongia communis, Salmonella enterica and Trypanosoma brucei. 3-(3h-imidazol-4-yl)prop-2-enoic acid was first documented in 2001 (PMID: 11669511). Urocanic acid is a very strong basic compound (based on its pKa) (PMID: 24397532) (PMID: 24627570).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0322164 (3-(3h-imidazol-4-yl)prop-2-enoic acid)


  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
Download

3D MOL for NP0322164 (3-(3h-imidazol-4-yl)prop-2-enoic acid)

     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
   -3.0061   -1.5893    0.6767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7415   -0.3689    0.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7495    0.5481    0.8384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3771    0.0488    0.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3926   -0.8080    0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9699   -0.3755   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1007   -1.1166   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1735   -0.3321   -0.4485 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191    0.9263   -0.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993    0.9213   -0.1069 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6303    1.5470    0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1682    1.1154    0.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6058   -1.8614    0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1132   -2.2033   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3784    1.7877   -0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8169    1.7605    0.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  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
Download

3D SDF for NP0322164 (3-(3h-imidazol-4-yl)prop-2-enoic acid)


  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>
NP0322164

> <DATABASE_NAME>
NP-MRD

> <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 NP0322164 (3-(3h-imidazol-4-yl)prop-2-enoic acid)

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PDB for NP0322164 (3-(3h-imidazol-4-yl)prop-2-enoic acid)
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 NP0322164 (3-(3h-imidazol-4-yl)prop-2-enoic acid)
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SMILES for NP0322164 (3-(3h-imidazol-4-yl)prop-2-enoic acid)
OC(=O)C=CC1=CN=CN1
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INCHI for NP0322164 (3-(3h-imidazol-4-yl)prop-2-enoic acid)
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 JSmol
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 Mass138.1260 Da
Monoisotopic Mass138.04293 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Coprinopsis atramentariaLOTUS Database
Hippospongia communisLOTUS Database
Salmonella entericaLOTUS Database
Trypanosoma bruceiLOTUS Database
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-0.86ChemAxon
logS-0.82ALOGPS
pKa (Strongest Acidic)3.91ChemAxon
pKa (Strongest Basic)6.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.98 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.89 m³·mol⁻¹ChemAxon
Polarizability12.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0062562  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  1. Kinuta M, Ohta J, Yamada H, Kinuta K, Abe T, Li SA, Otsuka A, Nakanishi A, Takei K: Determination of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]glutathione, a novel metabolite of L-histidine, in tissue extracts from sunlight-irradiated rat by capillary electrophoresis. Electrophoresis. 2001 Oct;22(16):3365-70. doi:  10.1002/1522-2683(200109)22:16<3365::AID-ELPS3365>3.0.CO;2-M. [PubMed:11669511  ] 
  2. Tuna D, Sobolewski AL, Domcke W: Photochemical mechanisms of radiationless deactivation processes in urocanic acid. J Phys Chem B. 2014 Jan 30;118(4):976-85. doi: 10.1021/jp411818j. Epub 2014 Jan  14. [PubMed:24397532  ] 
  3. Badawy AA: Pellagra and alcoholism: a biochemical perspective. Alcohol Alcohol. 2014 May-Jun;49(3):238-50. doi: 10.1093/alcalc/agu010. Epub 2014  Mar 13. [PubMed:24627570  ] 
  4. LOTUS database [Link]