4-imidazoleacetate (BioDeep_00000001352)

 

Secondary id: BioDeep_00000405500

human metabolite Endogenous blood metabolite


代谢物信息卡片


Imidazole-4-acetic acid hydrochloride

化学式: C5H6N2O2 (126.04292559999999)
中文名称: 咪唑-4-乙酸, 4-咪唑乙酸
谱图信息: 最多检出来源 Homo sapiens(blood) 6.53%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

4-imidazoleacetate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/4-imidazoleacetate (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000001352). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(c1c[nH]cn1)C(=O)O
InChI: InChI=1S/C5H6N2O2/c8-5(9)1-4-2-6-3-7-4/h2-3H,1H2,(H,6,7)(H,8,9)

描述信息

Imidazol-4-ylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by an imidazol-4-yl group. It has a role as a mouse metabolite. It is a monocarboxylic acid and a member of imidazoles. It derives from an acetic acid. It is a conjugate acid of an imidazol-4-ylacetate. It is a tautomer of an imidazol-5-ylacetic acid and a 2H-imidazol-4-ylacetic acid. Imidazoleacetic acid, also known as 4(5)-imidazoleacetate or IAA, 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. Imidazoleacetic acid exists in all living organisms, ranging from bacteria to humans. imidazoleacetic acid can be biosynthesized from imidazole-4-acetaldehyde through its interaction with the enzyme aldehyde dehydrogenase, mitochondrial. In humans, imidazoleacetic acid is involved in histidine metabolism. Outside of the human body, Imidazoleacetic acid has been detected, but not quantified in several different foods, such as chinese cinnamons, jostaberries, vanilla, butternut squash, and red rices. Imidazoleacetic acid is a potentially toxic compound. Imidazoleacetic acid is a metabolite product of Histamine metabolism.
Imidazoleacetic acid, also known as 4(5)-imidazoleacetate or imac, 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. Imidazoleacetic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Imidazoleacetic acid can be found in a number of food items such as grapefruit, garden onion (variety), black crowberry, and yellow zucchini, which makes imidazoleacetic acid a potential biomarker for the consumption of these food products. Imidazoleacetic acid can be found primarily in blood, cerebrospinal fluid (CSF), feces, and urine. In humans, imidazoleacetic acid is involved in the histidine metabolism. Imidazoleacetic acid is also involved in histidinemia, which is a metabolic disorder.

1H-Imidazole-5-acetic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=645-65-8 (retrieved 2024-07-16) (CAS RN: 645-65-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

23 个代谢物同义名

Imidazole-4-acetic acid hydrochloride; Imidazole-4-acetic acid, sodium salt; 2-(1H-imidazol-5-yl)acetic acid; 1H-Imidazol-4-ylacetic acid; 1H-Imidazole-4-acetic acid; 4(5)-Imidazoleacetic acid; Imidazol-4-ylacetic acid; Imidazolyl-4-acetic acid; Imidazole-4-acetic acid; 4-Imidazoleacetic acid; 1H-Imidazole-4-acetate; 4(5)-Imidazoleacetate; Imidazol-4-ylacetate; Imidazoleacetic acid; Imidazole-4-acetate; 4-Imidazoleacetate; Imidazole acetate; Imidazoleacetate; Lopac-I-0375; IMAC; IZC; IAA; Imidazoleacetic acid



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

2 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

  • Márjorie Castro Pinto Porfirio, Jonathan Barbosa Santos, Annie Nolasco Alves, Leandro Soares Santos, Renata Cristina Ferreira Bonomo, Rafael da Costa Ilhéu Fontan. Purification of pineapple bromelain by IMAC chromatography using chlorophyll-activated macroporous matrices. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2024 Feb; 1234(?):124027. doi: 10.1016/j.jchromb.2024.124027. [PMID: 38320436]
  • Ayça Serinbaş, Burcu Önal, Ömür Acet, Nalan Özdemir, Volha Dzmitruk, Inessa Halets-Bui, Dzmitry Shcharbin, Mehmet Odabaşı. A new application of inorganic sorbent for biomolecules: IMAC practice of Fe3+-nano flowers for DNA separation. Materials science & engineering. C, Materials for biological applications. 2020 Aug; 113(?):111020. doi: 10.1016/j.msec.2020.111020. [PMID: 32487418]
  • Alessandro Giraudo, Jacob Krall, Francesco Bavo, Birgitte Nielsen, Kenneth T Kongstad, Barbara Rolando, Rossella De Blasio, David E Gloriam, Rebekka Löffler, Louise Thiesen, Kasper Harpsøe, Karla Frydenvang, Donatella Boschi, Petrine Wellendorph, Marco L Lolli, Anders A Jensen, Bente Frølund. Five-Membered N-Heterocyclic Scaffolds as Novel Amino Bioisosteres at γ-Aminobutyric Acid (GABA) Type A Receptors and GABA Transporters. Journal of medicinal chemistry. 2019 06; 62(12):5797-5809. doi: 10.1021/acs.jmedchem.9b00026. [PMID: 31117514]
  • Silke Hack, Babette Wörlein, Georg Höfner, Jörg Pabel, Klaus T Wanner. Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors. European journal of medicinal chemistry. 2011 May; 46(5):1483-98. doi: 10.1016/j.ejmech.2011.01.042. [PMID: 21353350]
  • Xumin Zhang, Juanying Ye, Ole N Jensen, Peter Roepstorff. Highly Efficient Phosphopeptide Enrichment by Calcium Phosphate Precipitation Combined with Subsequent IMAC Enrichment. Molecular & cellular proteomics : MCP. 2007 Nov; 6(11):2032-42. doi: 10.1074/mcp.m700278-mcp200. [PMID: 17675664]
  • Martin Mortensen, Uffe Kristiansen, Bjarke Ebert, Bente Frølund, Povl Krogsgaard-Larsen, Trevor G Smart. Activation of single heteromeric GABA(A) receptor ion channels by full and partial agonists. The Journal of physiology. 2004 Jun; 557(Pt 2):389-413. doi: 10.1113/jphysiol.2003.054734. [PMID: 14990676]
  • D P Skoner, D A Gentile, P Fireman, K Cordoro, W J Doyle. Urinary histamine metabolite elevations during experimental influenza infection. Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology. 2001 Oct; 87(4):303-6. doi: 10.1016/s1081-1206(10)62244-2. [PMID: 11686422]
  • J K Khandelwal, G D Prell, A M Morrishow, J P Green. Presence and measurement of imidazoleacetic acid, a gamma-aminobutyric acid agonist, in rat brain and human cerebrospinal fluid. Journal of neurochemistry. 1989 Apr; 52(4):1107-13. doi: 10.1111/j.1471-4159.1989.tb01854.x. [PMID: 2926392]
  • M P Nava, A Fraile. Metabolism of histamine during pregnancy in the rat. Revista espanola de fisiologia. 1987 Dec; 43(4):483-9. doi: NULL. [PMID: 3129767]
  • Y Tsuruta, H Tomida, K Kohashi, Y Ohkura. Simultaneous determination of imidazoleacetic acid and N tau- and N pi-methylimidazoleacetic acids in human urine by high-performance liquid chromatography with fluorescence detection. Journal of chromatography. 1987 Apr; 416(1):63-9. doi: 10.1016/0378-4347(87)80485-1. [PMID: 3597642]
  • J K Khandelwal, T Kline, J P Green. Measurement of imidazoleacetic acid in urine by gas chromatography-mass spectrometry. Journal of chromatography. 1985 Oct; 343(2):249-57. doi: 10.1016/s0378-4347(00)84595-8. [PMID: 4066869]
  • P L Gray, P V Taberner. Evidence for GABA tolerance in barbiturate-dependent and withdrawn mice. Neuropharmacology. 1985 May; 24(5):437-44. doi: 10.1016/0028-3908(85)90029-2. [PMID: 2991801]
  • I Imamura, T Watanabe, Y Hase, Y Sakamoto, Y Fukuda, H Yamamoto, T Tsuruhara, H Wada. Histamine metabolism in patients with histidinemia: determination of urinary levels of histamine, N tau-methylhistamine, imidazole acetic acid, and its conjugate(s). Journal of biochemistry. 1984 Dec; 96(6):1925-9. doi: 10.1093/oxfordjournals.jbchem.a135027. [PMID: 6530403]
  • I Imamura, T Watanabe, K Maeyama, A Kubota, A Okada, H Wada. Effect of food intake on urinary excretions of histamine, N tau-methylhistamine, imidazole acetic acid and its conjugate(s) in humans and mice. Journal of biochemistry. 1984 Dec; 96(6):1931-7. doi: 10.1093/oxfordjournals.jbchem.a135028. [PMID: 6442293]
  • I Imamura, K Maeyama, H Wada, T Watanabe. Determination of imidazole acetic acid and its conjugate(s) levels in urine, serum and tissues of rats: studies on changes in their levels under various conditions. British journal of pharmacology. 1984 Jul; 82(3):701-7. doi: 10.1111/j.1476-5381.1984.tb10809.x. [PMID: 6743919]
  • H E Abboud. Catabolism of histamine in the isolated glomeruli and tubules of the rat kidney. Kidney international. 1983 Oct; 24(4):534-41. doi: 10.1038/ki.1983.190. [PMID: 6417393]
  • T Watanabe, H Kambe, I Imamura, Y Taguchi, T Tamura, H Wada. Method for enzymatic determination of imidazole acetic acid. Analytical biochemistry. 1983 Apr; 130(2):321-7. doi: 10.1016/0003-2697(83)90594-8. [PMID: 6869819]
  • M J Antonaccio, D W Snyder. Reductions in blood pressure, heart rate and renal sympathetic nervous discharge after imidazole-4-acetic acid: mediation through central gamma-aminobutyric acid (GABA) receptor stimulation. The Journal of pharmacology and experimental therapeutics. 1981 Jul; 218(1):200-5. doi: NULL. [PMID: 6264068]
  • E Escudero, A Fraile. Comparative metabolism of histamine in two Amphibia anura. Agents and actions. 1979 Oct; 9(4):310-3. doi: 10.1007/bf01970653. [PMID: 517328]
  • J W KERR. IDENTIFICATION OF HISTAMINE METABOLITE 1-METHYL, 4-IMIDAZOLE ACETIC ACID IN HUMAN URINE AND ITS ABSENCE IN STATUS ASTHMATICUS. British medical journal. 1964 Sep; 2(5409):606-8. doi: 10.1136/bmj.2.5409.606. [PMID: 14171067]
  • S E LINDELL, K NILSSON, B E ROOS, H WESTLING. The effect of enzyme inhibitors on histamine catabolism in man. British journal of pharmacology and chemotherapy. 1960 Jun; 15(?):351-5. doi: 10.1111/j.1476-5381.1960.tb01255.x. [PMID: 14417081]
  • S E LINDELL, R W SCHAYER. Metabolism of injected [14C] histamine in the kidney of the dog. British journal of pharmacology and chemotherapy. 1958 Mar; 13(1):52-3. doi: 10.1111/j.1476-5381.1958.tb00189.x. [PMID: 13523134]
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