Record Information
Version1.0
Creation date2010-04-08 22:04:46 UTC
Update date2019-11-26 02:55:37 UTC
Primary IDFDB000921
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameUrocanic acid
DescriptionUrocanic acid is an intermediate in the catabolism of L-histidine.; Urocanic is a breakdown (deamination) product of histidine. In the liver, urocanic acid is an intermediate in the conversion of histidine to glutamic acid, whereas in the epidermis, it accumulates and may be both a UV protectant and an immunoregulator. Urocanic acid (UA) exists as a trans isomer (t-UA, approximately 30 mg/cm2) in the uppermost layer of the skin (stratum corneum). t-UA is formed as the cells of the second layer of skin become metabolically inactive. During this process, proteins and membranes degrade, histidine is released, and histidase (histidine ammonia lyase) catalyzes the deamination of histidine to form t-UA. t-UA accumulates in the epidermis until removal by either the monthly skin renewal cycle or sweat. Upon absorption of UV light, the naturally occurring t-UA isomerizes to its cis form, c-UA. Because DNA lesions (e.g., pyrimidine dimers) in the lower epidermis can result from UV-B absorption, initial research proposed that t-UA acted as a natural sunscreen absorbing UV-B in the stratum corneum before the damaging rays could penetrate into lower epidermal zones. Researchers have found that c-UA also suppresses contact hypersensitivity and delayed hypersensitivity, reduces the Langerhans cell count in the epidermis, prolongs skin-graft survival time, and affects natural killer cell activity. Urocanic acid is found in mung bean.
CAS Number104-98-3
Structure
Thumb
Synonyms
SynonymSource
(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
(2e)-3-(1H-Imidazol-4-yl)acrylateGenerator
(e)-3-(1H-Imidazol-4-yl)-2-propenoateGenerator
3-(1H-Imidazol-4-yl)-2-propenoatebiospider
3-(1H-Imidazol-4-yl)-2-propenoic acidHMDB
3-(1H-Imidazol-4-yl)-2-propenoic acid, 9CIdb_source
3-(1H-Imidazol-4-yl)acrylatebiospider
3-(1H-Imidazol-4-yl)acrylic acidbiospider
3-(4-Imidazolyl)acrylatebiospider
3-(4-Imidazolyl)acrylic acidHMDB
4-Imidazoleacrylic acid, 8CIdb_source
5-ImidazoleacrylateHMDB
5-Imidazoleacrylate;imidazoleacrylic acidbiospider
5-Imidazoleacrylic acidHMDB
Imidazole-4-acrylatebiospider
Imidazole-4-acrylic acidHMDB
Imidazoleacrylic acidHMDB
Trans-urocanatebiospider
UrocanateGenerator
Urocaninic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility21 g/LALOGPS
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
Chemical FormulaC6H6N2O2
IUPAC name(2Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(=O)\C=C/C1=CN=CN1
Average Molecular Weight138.124
Monoisotopic Molecular Weight138.042927446
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 52.17%; H 4.38%; N 20.28%; O 23.17%DFC
Melting PointMp 243-245°DFC
Boiling PointNot Available
Experimental Water Solubility1.5 mg/mL at 17 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSUrocanic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9500000000-214759fcc6a8a9e5c0feSpectrum
Predicted GC-MSUrocanic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9500000000-79bb3529b72209d3d144Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-1900000000-dac4165382f541a26a032016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0076-8900000000-6da8eb6b76055856b7142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-ab76de8a8f1873f63de62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-173e1f32b118424e132d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-5900000000-b1ebc285fc95a34dc7b12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9200000000-66f717c0018108bc77692016-08-03View Spectrum
NMRNot Available
ChemSpider ID643824
ChEMBL IDCHEMBL1236602
KEGG Compound IDC00785
Pubchem Compound ID736715
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01971
HMDB IDHMDB00301
CRC / DFC (Dictionary of Food Compounds) IDBMT82-F:BMT82-F
EAFUS IDNot Available
Dr. Duke IDUROCANIC-ACID
BIGG ID35990
KNApSAcK IDNot Available
HET IDURO
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDUrocanic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Histidine ammonia-lyaseHALP42357
Pathways
NameSMPDB LinkKEGG Link
Ammonia RecyclingSMP00009 map00910
Histidine MetabolismSMP00044 map00340
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).