Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:04:46 UTC |
---|
Update date | 2019-11-26 02:55:37 UTC |
---|
Primary ID | FDB000921 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | Urocanic acid |
---|
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. |
---|
CAS Number | 104-98-3 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
(Z)-Imidazole-4-acrylic acid | ChEBI | (Z)-Imidazole-4-acrylate | Generator | (e)-Urocanate | Generator | (2E)-3-(1H-Imidazol-4-yl)acrylic acid | HMDB | (2E)-3-(1H-Imidazol-4-yl)prop-2-enoic acid | HMDB | (e)-3-(1H-Imidazol-4-yl)-2-propenoic acid | HMDB | 3-(1H-Imidazol-4-yl)-(e)-2-propenoic acid | HMDB | 3-(1H-Imidazol-4-yl)prop-2-enoic acid | HMDB | 3-(1H-Imidazol-5-yl)-2-propenoic acid | HMDB | 3-Imidazol-4-ylacrylic acid | HMDB | cis-Urocanic acid | HMDB | Imidazole-4-propene-2-enoic acid | HMDB | trans-Urocanic acid | HMDB | Urocanic acid | HMDB | Urocanic acid, cis | HMDB | (2e)-3-(1H-Imidazol-4-yl)acrylate | Generator | (e)-3-(1H-Imidazol-4-yl)-2-propenoate | Generator | 3-(1H-Imidazol-4-yl)-2-propenoate | biospider | 3-(1H-Imidazol-4-yl)-2-propenoic acid | HMDB | 3-(1H-Imidazol-4-yl)-2-propenoic acid, 9CI | db_source | 3-(1H-Imidazol-4-yl)acrylate | biospider | 3-(1H-Imidazol-4-yl)acrylic acid | biospider | 3-(4-Imidazolyl)acrylate | biospider | 3-(4-Imidazolyl)acrylic acid | HMDB | 4-Imidazoleacrylic acid, 8CI | db_source | 5-Imidazoleacrylate | HMDB | 5-Imidazoleacrylate;imidazoleacrylic acid | biospider | 5-Imidazoleacrylic acid | HMDB | Imidazole-4-acrylate | biospider | Imidazole-4-acrylic acid | HMDB | Imidazoleacrylic acid | HMDB | Trans-urocanate | biospider | Urocanate | Generator | Urocaninic acid | db_source |
|
---|
Predicted Properties | |
---|
Chemical Formula | C6H6N2O2 |
---|
IUPAC name | (2Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid |
---|
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 |
---|
Isomeric SMILES | OC(=O)\C=C/C1=CN=CN1 |
---|
Average Molecular Weight | 138.124 |
---|
Monoisotopic Molecular Weight | 138.042927446 |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Azoles |
---|
Sub Class | Imidazoles |
---|
Direct Parent | Imidazolyl 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 Framework | Aromatic heteromonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Role | Biological role: |
---|
Physico-Chemical Properties |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Solid | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 52.17%; H 4.38%; N 20.28%; O 23.17% | DFC |
---|
Melting Point | Mp 243-245° | DFC |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | 1.5 mg/mL at 17 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
---|
Experimental logP | Not Available | |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
Predicted GC-MS | Urocanic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9500000000-214759fcc6a8a9e5c0fe | Spectrum | Predicted GC-MS | Urocanic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-9500000000-79bb3529b72209d3d144 | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0079-1900000000-dac4165382f541a26a03 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0076-8900000000-6da8eb6b76055856b714 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-9000000000-ab76de8a8f1873f63de6 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-1900000000-173e1f32b118424e132d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000l-5900000000-b1ebc285fc95a34dc7b1 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9200000000-66f717c0018108bc7769 | 2016-08-03 | View Spectrum |
|
---|
NMR | Not Available |
---|
External Links |
---|
ChemSpider ID | 643824 |
---|
ChEMBL ID | CHEMBL1236602 |
---|
KEGG Compound ID | C00785 |
---|
Pubchem Compound ID | 736715 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | DB01971 |
---|
HMDB ID | HMDB00301 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | BMT82-F:BMT82-F |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | UROCANIC-ACID |
---|
BIGG ID | 35990 |
---|
KNApSAcK ID | Not Available |
---|
HET ID | URO |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Urocanic acid |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Not Available |
---|
Enzymes | Name | Gene Name | UniProt ID |
---|
Histidine ammonia-lyase | HAL | P42357 |
|
---|
Pathways | |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | show |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
|
---|