Urocanic acid (BioDeep_00000001482)

 

Secondary id: BioDeep_00000265232

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


(2E)-3-(1H-Imidazol-5-yl)-2-propenoic acid

化学式: C6H6N2O2 (138.0429256)
中文名称: 4-咪唑丙烯酸, 尿烷酸, 反式尿刊酸, 尿酸
谱图信息: 最多检出来源 Homo sapiens(feces) 0.69%

Reviewed

Last reviewed on 2024-07-17.

Cite this Page

Urocanic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/urocanic_acid (retrieved 2024-11-24) (BioDeep RN: BioDeep_00000001482). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(=C\C(=O)O)/c1c[nH]cn1
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+

描述信息

Urocanic acid (CAS: 104-98-3) 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 the 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. (E)-Urocanic acid is found in mushrooms. It has been isolated from Coprinus atramentarius (common ink cap) and Phallus impudicus (common stinkhorn).
Trans-urocanic acid, also known as 4-imidazoleacrylic acid or urocanate, belongs to imidazolyl carboxylic acids and derivatives class of compounds. Those are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. Trans-urocanic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Trans-urocanic acid can be found in mung bean, which makes trans-urocanic acid a potential biomarker for the consumption of this food product. Trans-urocanic acid can be found primarily in most biofluids, including sweat, feces, blood, and urine, as well as in human liver and skin tissues. Trans-urocanic acid exists in all living organisms, ranging from bacteria to humans. In humans, trans-urocanic acid is involved in the histidine metabolism. Trans-urocanic acid is also involved in a couple of metabolic disorders, which include ammonia recycling and histidinemia.
Urocanic acid, produced in the upper layers of mammalian skin, is a major absorber of ultraviolet radiation (UVR).
Urocanic acid, produced in the upper layers of mammalian skin, is a major absorber of ultraviolet radiation (UVR).

同义名列表

29 个代谢物同义名

(2E)-3-(1H-Imidazol-5-yl)-2-propenoic acid; (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid; (e)-3-(1H-Imidazol-4-yl)-2-propenoic acid; (e)-3-(Imidazol-4-yl)-2-propenoic acid; (e)-3-(1H-Imidazol-4-yl)-2-propenoate; 3-(1H-Imidazol-4-yl)-2-propenoic acid; (2E)-3-(1H-Imidazol-4-yl)acrylic acid; (2E)-3-(1H-Imidazol-4-yl)acrylate; 3-(1H-Imidazol-4-yl)-2-propenoate; (e)-3-(4-Imidazolyl)acrylic acid; 3-(1H-Imidazol-4-yl)acrylic acid; 3-(4-Imidazolyl)acrylic acid; 3-(1H-Imidazol-4-yl)acrylate; Imidazole-4-acrylic acid; 3-(4-Imidazolyl)acrylate; Acid, glyoxalinylacrylic; 5-Imidazoleacrylic acid; Glyoxalinylacrylic acid; Imidazoleacrylic acid; Imidazole-4-acrylate; 5-Imidazoleacrylate; trans-Urocanic acid; (e)-Urocanic acid; Acid, urocanic; Urocanic acid; Urocanate; Urocanic acid; Urocanate; Urocanic acid



数据库引用编号

39 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(0)

PlantCyc(0)

代谢反应

70 个相关的代谢反应过程信息。

Reactome(56)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(13)

  • Histidine Metabolism: Carnosine + Water ⟶ -Alanine + L-Histidine
  • Histidinemia: Carnosine + Water ⟶ -Alanine + L-Histidine
  • Histidine Metabolism: Carnosine + Water ⟶ -Alanine + L-Histidine
  • Histidine Metabolism: -Alanine + Adenosine triphosphate + L-Histidine ⟶ Adenosine diphosphate + Carnosine + Phosphate
  • Histidinemia: Carnosine + Water ⟶ -Alanine + L-Histidine
  • Histidine Metabolism: Carnosine + Water ⟶ -Alanine + L-Histidine
  • Histidinemia: -Alanine + Adenosine triphosphate + L-Histidine ⟶ Adenosine diphosphate + Carnosine + Phosphate
  • Ammonia Recycling: Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water ⟶ Adenosine monophosphate + L-Asparagine + L-Glutamic acid + Pyrophosphate
  • Ammonia Recycling: Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water ⟶ Adenosine monophosphate + L-Asparagine + L-Glutamic acid + Pyrophosphate
  • Ammonia Recycling: Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water ⟶ Adenosine monophosphate + L-Asparagine + L-Glutamic acid + Pyrophosphate
  • Ammonia Recycling: Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water ⟶ Adenosine monophosphate + L-Asparagine + L-Glutamic acid + Pyrophosphate
  • Ammonia Recycling: Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water ⟶ Adenosine monophosphate + L-Asparagine + L-Glutamic acid + Pyrophosphate
  • Ammonia Recycling: Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water ⟶ Adenosine monophosphate + L-Asparagine + L-Glutamic acid + Pyrophosphate

PharmGKB(0)

21 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Xu-Dong Yu, Yan-Xin Mo, Zhiming He, James Reilly, Shao-Wen Tian, Xinhua Shu. Urocanic acid enhances memory consolidation and reconsolidation in novel object recognition task. Biochemical and biophysical research communications. 2021 11; 579(?):62-68. doi: 10.1016/j.bbrc.2021.09.055. [PMID: 34587556]
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  • Karolina Bossak-Ahmad, Marta D Wiśniewska, Wojciech Bal, Simon C Drew, Tomasz Frączyk. Ternary Cu(II) Complex with GHK Peptide and Cis-Urocanic Acid as a Potential Physiologically Functional Copper Chelate. International journal of molecular sciences. 2020 Aug; 21(17):. doi: 10.3390/ijms21176190. [PMID: 32867146]
  • Juyeon Kim, Youngae Jung, Eunok Lee, Seoyeong Jang, Do Hyun Ryu, Oran Kwon, Geum-Sook Hwang. Urinary Metabolomic Profiling Analysis and Evaluation of the Effect of Ecklonia cava Extract Intake. Nutrients. 2020 May; 12(5):. doi: 10.3390/nu12051407. [PMID: 32422870]
  • Wei-Liang Chen, Fang Li, Yan Tang, Shu-di Yang, Ji-Zhao Li, Zhi-Qiang Yuan, Yang Liu, Xiao-Feng Zhou, Chun Liu, Xue-Nong Zhang. Stepwise pH-responsive nanoparticles for enhanced cellular uptake and on-demand intracellular release of doxorubicin. International journal of nanomedicine. 2017; 12(?):4241-4256. doi: 10.2147/ijn.s129748. [PMID: 28652730]
  • Yvonne Konkol, Jenni Bernoulli, Tomi Streng, Katarina Jääskeläinen, Jarmo Laihia, Lasse Leino. Intravesical treatment with cis-urocanic acid improves bladder function in rat model of acute bladder inflammation. Neurourology and urodynamics. 2016 09; 35(7):786-91. doi: 10.1002/nau.22818. [PMID: 26175302]
  • Hanna-Mari Jauhonen, Eeva Kari, Liisa Pylkkänen, Jutta Poutanen, Jarmo Laihia, Kai Kaarniranta, Lasse Leino. A randomized phase I clinical study of cis-urocanic acid eye drops in healthy adult subjects. Acta ophthalmologica. 2015 Jun; 93(4):368-76. doi: 10.1111/aos.12651. [PMID: 25611308]
  • Olga María Palomino. Current knowledge in Polypodium leucotomos effect on skin protection. Archives of dermatological research. 2015 Apr; 307(3):199-209. doi: 10.1007/s00403-014-1535-x. [PMID: 25539991]
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  • Juha M Peltonen, Liisa Pylkkänen, Christer T Jansén, Iina Volanen, Terhi Lehtinen, Jarmo K Laihia, Lasse Leino. Three randomised phase I/IIa trials of 5\% cis-urocanic acid emulsion cream in healthy adult subjects and in patients with atopic dermatitis. Acta dermato-venereologica. 2014 Jul; 94(4):415-20. doi: 10.2340/00015555-1735. [PMID: 24284985]
  • Kateřina Vávrová, Dominika Henkes, Kay Strüver, Michaela Sochorová, Barbora Školová, Madeleine Y Witting, Wolfgang Friess, Stephan Schreml, Robert J Meier, Monika Schäfer-Korting, Joachim W Fluhr, Sarah Küchler. Filaggrin deficiency leads to impaired lipid profile and altered acidification pathways in a 3D skin construct. The Journal of investigative dermatology. 2014 Mar; 134(3):746-753. doi: 10.1038/jid.2013.402. [PMID: 24061166]
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