Cis-Urocanic acid

Cis-Urocanic acid
Identifiers
	IUPAC name (Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid;
CAS Number	7699-35-6;
PubChem CID	1549103;
ChemSpider	1266070;
UNII	5LM7WD7VIC;
ChEBI	CHEBI:30818;
ChEMBL	ChEMBL1316726;
CompTox Dashboard (EPA)	DTXSID901316398 ;
Chemical and physical data
Formula	C6H6N2O2
Molar mass	138.126 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=C(NC=N1)/C=C\C(=O)O;
	InChI InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1-; Key:LOIYMIARKYCTBW-UPHRSURJSA-N;

cis-Urocanic acid (cis-UCA) is a chemical compound produced by ultraviolet irradiation of trans-urocanic acid, a metabolite naturally formed in the body from histidine. cis-Urocanic acid is suspected of involvement in the development of skin cancer. It acts as an immunosuppressant through action as an agonist of the 5-HT_2A receptor, and blocking this receptor has been shown to reduce cis-UCA mediated photocarcinogenesis. However the immunomodulatory effects of cis-UCA are complex and also involve other pathways, and at low levels it shows antiinflammatory actions and may be protective against UV damage in the cornea and retina. Measuring cis-UCA has been proposed as a sensitive method to detect sub-erythemal response to UVB, and thus a means to assess the UVR protection of suncreams.

Identifiers

IUPAC name (Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid
CAS Number	7699-35-6
PubChem CID	1549103
ChemSpider	1266070
UNII	5LM7WD7VIC
ChEBI	CHEBI:30818
ChEMBL	ChEMBL1316726
CompTox Dashboard (EPA)	DTXSID901316398
Chemical and physical data
Formula	C₆H₆N₂O₂
Molar mass	138.126 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1=C(NC=N1)/C=C\C(=O)O
InChI InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1- Key:LOIYMIARKYCTBW-UPHRSURJSA-N