cis-Urocanic acid
PubChem CID: 1549103
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| Compound Synonyms | cis-Urocanic acid, 7699-35-6, Imidazole-4-acrylic acid, (Z)-, cis-UCA, (Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid, (Z)-Imidazole-4-acrylic acid, Urocanic acid, cis-, (E)-Urocanic acid, 5LM7WD7VIC, CHEBI:30818, (Z)-3-(3H-imidazol-4-yl)prop-2-enoic Acid, NSC-407934, (Z)-3-(1H-Imidazol-5-yl)acrylic acid, cis-3-(1H-imidazol-4-yl)-2-propenoic acid, (2Z)-3-(1H-imidazol-4-yl)prop-2-enoic acid, UNII-5LM7WD7VIC, cis-Urocanic acid?, NSC 407934, Lopac-U-7500, SCHEMBL1755678, CHEMBL1316726, SCHEMBL12963908, LOIYMIARKYCTBW-UPHRSURJSA-N, DTXSID901316398, MFCD11045310, AKOS030532710, HY-113008A, NCGC00016079-01, DA-51937, MS-22807, CS-0109435, G13726, cis-Urocanic acid, >=98% (HPLC), solid (fluffy), (E)-3-(3H-IMIDAZOL-4-YL)PROP-2-ENOIC ACID, BRD-K25146005-001-01-0, Q27113993, 2-PROPENOIC ACID, 3-(1H-IMIDAZOL-5-YL)-, (2Z)- |
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| Topological Polar Surface Area | 66.0 |
| Hydrogen Bond Donor Count | 2.0 |
| Heavy Atom Count | 10.0 |
| Pathway Kegg Map Id | map00910, map00340 |
| Description | Urocanic 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. |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 156.0 |
| Database Name | fooddb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Enzyme Uniprot Id | P42357 |
| Iupac Name | (Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid |
| Nih Violation | False |
| Class | Azoles |
| Xlogp | 0.0 |
| Superclass | Organoheterocyclic compounds |
| Is Pains | False |
| Subclass | Imidazoles |
| Molecular Formula | C6H6N2O2 |
| Inchi Key | LOIYMIARKYCTBW-UPHRSURJSA-N |
| Rotatable Bond Count | 2.0 |
| State | Solid |
| Synonyms | (2e)-3-(1H-Imidazol-4-yl)acrylate, (e)-3-(1H-Imidazol-4-yl)-2-propenoate, 3-(1H-Imidazol-4-yl)-2-propenoate, 3-(1H-Imidazol-4-yl)-2-propenoic acid, 3-(1H-Imidazol-4-yl)-2-propenoic acid, 9CI, 3-(1H-Imidazol-4-yl)acrylate, 3-(1H-Imidazol-4-yl)acrylic acid, 3-(4-Imidazolyl)acrylate, 3-(4-Imidazolyl)acrylic acid, 4-Imidazoleacrylic acid, 8CI, 5-Imidazoleacrylate, 5-Imidazoleacrylate, imidazoleacrylic acid, 5-Imidazoleacrylic acid, Imidazole-4-acrylate, Imidazole-4-acrylic acid, Imidazoleacrylic acid, Trans-urocanate, Urocanate, Urocaninic acid, (2E)-3-(1H-imidazol-4-yl)acrylic acid, (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid, (E)-3-(1H-imidazol-4-yl)-2-propenoic acid, (Z)-Imidazole-4-acrylate, (Z)-Imidazole-4-acrylic acid, 2-Propenoic acid, 3-(1H-imidazol-4-yl)-, (E)-, 2-Propenoic acid, 3-(1H-imidazol-5-yl)-, 3-(1H-Imidazol-4-yl)-(e)-2-propenoic acid, 3-(1H-imidazol-4-yl)prop-2-enoic acid, 3-(1H-Imidazol-5-yl)-2-propenoic acid, 3-Imidazol-4-ylacrylic acid, cis-Urocanate, Cis-urocanic acid, Imidazole-4-acrylic acid, (Z)-, Imidazole-4-propene-2-enoic acid, Imidazole-4-propene-2-enoic acid [Urocanic acid], Trans-urocanic acid, Urocanic acid, Urocanic acid, cis |
| Substituent Name | Imidazolyl carboxylic acid derivative, Heteroaromatic compound, Azacycle, Monocarboxylic acid or derivatives, Carboxylic acid, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Organonitrogen compound, Carbonyl group, Aromatic heteromonocyclic compound |
| Compound Name | cis-Urocanic acid |
| Kingdom | Organic compounds |
| Exact Mass | 138.043 |
| Formal Charge | 0.0 |
| Brenk Violation | True |
| Monoisotopic Mass | 138.043 |
| Hydrogen Bond Acceptor Count | 3.0 |
| Molecular Weight | 138.12 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 1.0 |
| 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- |
| Smiles | C1=C(NC=N1)/C=C\C(=O)O |
| Defined Bond Stereocenter Count | 1.0 |
- 1. Outgoing r'ship
FOUND_INto/from Vigna Radiata (Plant) Rel Props:Source_db:fooddb_chem_all