p-Cresol glucuronide (BioDeep_00000023415)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acid

化学式: C13H16O7 (284.0896)
中文名称: P-苯甲基-β-D-葡萄糖酮酸, 对甲酚葡糖醛酸
谱图信息: 最多检出来源 Homo sapiens(blood) 48.04%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

p-Cresol glucuronide. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/p-cresol_glucuronide (retrieved 2025-01-31) (BioDeep RN: BioDeep_00000023415). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC1=CC=C(C=C1)OC2C(C(C(C(O2)C(=O)O)O)O)O
InChI: InChI=1S/C13H16O7/c1-6-2-4-7(5-3-6)19-13-10(16)8(14)9(15)11(20-13)12(17)18/h2-5,8-11,13-16H,1H3,(H,17,18)/t8-,9-,10+,11-,13+/m0/s1

描述信息

p-Cresol glucuronide is a glucuronide derivative a p-Cresol that is typically excreted in the urine. P-Cresol (the precursor of p-cresol sulfate (PCS) and p-cresol glucuronide (PCG)) is mainly generated as an end product of tyrosine biotransformation by anaerobic intestinal bacteria. During passage through the colonic mucosa and liver, sulfatation and glucuronidation generates p-Cresol sulfate (as the most preponderant metabolite) and p-Cresol glucuronide (at markedly lower concentrations) (PMID: 23826225). Cresols are known as methylphenols. Cresols are used to dissolve other chemicals, such as disinfectants and deodorizers. They are also used to make specific chemicals that kill insect pests. Cresol solutions are used as household cleaners and disinfectants such as Lysol. Cresol solutions can also be found in photographic developers. In the past, cresol solutions have been used as antiseptics in surgery, but they have been largely displaced in this role by less toxic compounds. Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar, and in brown mixtures such as creosote, cresolene and cresylic acids, which are wood preservatives. Microbes in the soil and water produce cresols when they break down materials in the environment. Most exposures to cresols are at very low levels that are not harmful. When cresols are breathed, ingested, or applied to the skin at very high levels, they can be very harmful. Effects observed in people include irritation and burning of skin, eyes, mouth, and throat; abdominal pain and vomiting. Cresols are also a chemical component found in Sharpie Markers. P-cresol is a major component in pig odor.
p-Cresol glucuronide is a glucuronide derivative a p-Cresol that is typically excreted in the urine. Cresols are known as methylphenols. Cresols are used to dissolve other chemicals, such as disinfectants and deodorizers. They are also used to make specific chemicals that kill insect pests. Cresol solutions are used as household cleaners and disinfectants such as Lysol. Cresol solutions can also be found in photographic developers. In the past, cresol solutions have been used as antiseptics in surgery, but they have been largely displaced in this role by less toxic compounds. Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar, and in brown mixtures such as creosote, cresolene and cresylic acids, which are wood preservatives. Microbes in soil and water produce cresols when they break down materials in the environment. Most exposures to cresols are at very low levels that are not harmful. When cresols are breathed, ingested, or applied to the skin at very high levels, they can be very harmful. Effects observed in people include irritation and burning of skin, eyes, mouth, and throat; abdominal pain and vomiting. Cresols are also a chemical component found in Sharpie Markers. P-cresol is a major component in pig odor. [HMDB]

同义名列表

19 个代谢物同义名

(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acid; (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylate; 4-Methylphenyl beta-D-glucopyranosiduronic acid; 4-Methylphenyl beta-D-glucopyranosiduronate; p-Cresyl-beta-D-glucuronide; P-TOLYL-BETA-D-GLUCURONIDE; p-Cresyl-β-D-glucuronide; p-Cresyl-b-D-glucuronide; p-Tolyl b-D-glucuronide; p-Tolyl β-D-glucuronide; p-Tolyl--D-glucuronide; p-Cresol glucuronide; p-Cresyl glucuronide; 4-Cresylglucuronide; p-Cresylglucuronide; Cresol glucuronide; Cresyl glucuronide; Cresylglucuronide; pCG



数据库引用编号

9 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

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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。

亚细胞结构定位 关联基因列表


文献列表

  • Karl M Weigand, Tom J J Schirris, Megan Houweling, Jeroen J M W van den Heuvel, Jan B Koenderink, Anita C A Dankers, Frans G M Russel, Rick Greupink. Uremic solutes modulate hepatic bile acid handling and induce mitochondrial toxicity. Toxicology in vitro : an international journal published in association with BIBRA. 2019 Apr; 56(?):52-61. doi: 10.1016/j.tiv.2019.01.003. [PMID: 30639138]
  • Michael Pignanelli, Chrysi Bogiatzi, Gregory Gloor, Emma Allen-Vercoe, Gregor Reid, Bradley L Urquhart, Kelsey N Ruetz, Thomas J Velenosi, J David Spence. Moderate Renal Impairment and Toxic Metabolites Produced by the Intestinal Microbiome: Dietary Implications. Journal of renal nutrition : the official journal of the Council on Renal Nutrition of the National Kidney Foundation. 2019 01; 29(1):55-64. doi: 10.1053/j.jrn.2018.05.007. [PMID: 30100156]
  • Shanmugakumar Chinnappa, Yu-Kang Tu, Yi Chun Yeh, Griet Glorieux, Raymond Vanholder, Andrew Mooney. Association between Protein-Bound Uremic Toxins and Asymptomatic Cardiac Dysfunction in Patients with Chronic Kidney Disease. Toxins. 2018 12; 10(12):. doi: 10.3390/toxins10120520. [PMID: 30563136]
  • Dan Yi, Elisa Bernardes Monteiro, Stéphane Chambert, Hédi A Soula, Julio B Daleprane, Christophe O Soulage. Determination of the binding properties of p-cresyl glucuronide to human serum albumin. Biochimie. 2018 Jul; 150(?):1-7. doi: 10.1016/j.biochi.2018.04.019. [PMID: 29705133]
  • Laetitia Koppe, Pascaline M Alix, Marine L Croze, Stéphane Chambert, Raymond Vanholder, Griet Glorieux, Denis Fouque, Christophe O Soulage. p-Cresyl glucuronide is a major metabolite of p-cresol in mouse: in contrast to p-cresyl sulphate, p-cresyl glucuronide fails to promote insulin resistance. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2017 Dec; 32(12):2000-2009. doi: 10.1093/ndt/gfx089. [PMID: 28992089]
  • Ruben Poesen, Pieter Evenepoel, Henriette de Loor, Dirk Kuypers, Patrick Augustijns, Björn Meijers. Metabolism, Protein Binding, and Renal Clearance of Microbiota-Derived p-Cresol in Patients with CKD. Clinical journal of the American Society of Nephrology : CJASN. 2016 07; 11(7):1136-44. doi: 10.2215/cjn.00160116. [PMID: 27084876]
  • Henricus A M Mutsaers, Pedro Caetano-Pinto, Andries E M Seegers, Anita C A Dankers, Petra H H van den Broek, Jack F M Wetzels, Jan A J G van den Brand, Lambertus P van den Heuvel, Joost G Hoenderop, Martijn J G Wilmer, Rosalinde Masereeuw. Proximal tubular efflux transporters involved in renal excretion of p-cresyl sulfate and p-cresyl glucuronide: Implications for chronic kidney disease pathophysiology. Toxicology in vitro : an international journal published in association with BIBRA. 2015 Oct; 29(7):1868-77. doi: 10.1016/j.tiv.2015.07.020. [PMID: 26216510]
  • Olivier Deltombe, Wim Van Biesen, Griet Glorieux, Ziad Massy, Annemieke Dhondt, Sunny Eloot. Exploring Protein Binding of Uremic Toxins in Patients with Different Stages of Chronic Kidney Disease and during Hemodialysis. Toxins. 2015 Sep; 7(10):3933-46. doi: 10.3390/toxins7103933. [PMID: 26426048]
  • N Neirynck, R Vanholder, E Schepers, S Eloot, A Pletinck, G Glorieux. An update on uremic toxins. International urology and nephrology. 2013 Feb; 45(1):139-50. doi: 10.1007/s11255-012-0258-1. [PMID: 22893494]
  • Jente Boelaert, Frédéric Lynen, Griet Glorieux, Sunny Eloot, Maria Van Landschoot, Marie-Anne Waterloos, Pat Sandra, Raymond Vanholder. A novel UPLC-MS-MS method for simultaneous determination of seven uremic retention toxins with cardiovascular relevance in chronic kidney disease patients. Analytical and bioanalytical chemistry. 2013 Feb; 405(6):1937-47. doi: 10.1007/s00216-012-6636-9. [PMID: 23307120]
  • Sophie Liabeuf, Griet Glorieux, Aurelie Lenglet, Momar Diouf, Eva Schepers, Lucie Desjardins, Gabriel Choukroun, Raymond Vanholder, Ziad A Massy. Does p-cresylglucuronide have the same impact on mortality as other protein-bound uremic toxins?. PloS one. 2013; 8(6):e67168. doi: 10.1371/journal.pone.0067168. [PMID: 23826225]
  • Natalie Meert, Eva Schepers, Griet Glorieux, Maria Van Landschoot, Jan L Goeman, Marie-Anne Waterloos, Annemieke Dhondt, Johan Van der Eycken, Raymond Vanholder. Novel method for simultaneous determination of p-cresylsulphate and p-cresylglucuronide: clinical data and pathophysiological implications. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2012 Jun; 27(6):2388-96. doi: 10.1093/ndt/gfr672. [PMID: 22167586]
  • Yulan Wang, Jürg Utzinger, Shu-Hua Xiao, Jian Xue, Jeremy K Nicholson, Marcel Tanner, Burton H Singer, Elaine Holmes. System level metabolic effects of a Schistosoma japonicum infection in the Syrian hamster. Molecular and biochemical parasitology. 2006 Mar; 146(1):1-9. doi: 10.1016/j.molbiopara.2005.10.010. [PMID: 16337285]
  • Henriette de Loor, Bert Bammens, Pieter Evenepoel, Vicky De Preter, Kristin Verbeke. Gas chromatographic-mass spectrometric analysis for measurement of p-cresol and its conjugated metabolites in uremic and normal serum. Clinical chemistry. 2005 Aug; 51(8):1535-8. doi: 10.1373/clinchem.2005.050781. [PMID: 16040852]
  • Gerrit Lesaffer, Rita De Smet, Tommy D'Heuvaert, Frans M Belpaire, Norbert Lameire, Raymond Vanholder. Comparative kinetics of the uremic toxin p-cresol versus creatinine in rats with and without renal failure. Kidney international. 2003 Oct; 64(4):1365-73. doi: 10.1046/j.1523-1755.2003.00228.x. [PMID: 12969155]