Phenylacetylglutamine (BioDeep_00000002938)

 

Secondary id: BioDeep_00000404022

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(2S)-5-amino-5-oxo-2-[(2-phenylacetyl)amino]pentanoic acid

化学式: C13H16N2O4 (264.1110016)
中文名称: N-苯乙酰基-L-谷氨酰胺, 苯乙酰谷氨酰胺, 苯乙酰谷氨酰胺
谱图信息: 最多检出来源 Homo sapiens(blood) 0.02%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Phenylacetylglutamine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/phenylacetylglutamine (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000002938). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=CC=C(C=C1)CC(=O)NC(CCC(=O)N)C(=O)O
InChI: InChI=1S/C13H16N2O4/c14-11(16)7-6-10(13(18)19)15-12(17)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,17)(H,18,19)

描述信息

Phenylacetylglutamine is a product formed from the conjugation of phenylacetate and glutamine. Technically, it is the amino acid acetylation product of phenylacetate (or phenylbutyrate after beta-oxidation). Phenylacetylglutamine is a normal constituent of human urine, but other mammals such as the dog, cat, rat, monkey, sheep, and horse do not excrete this compound. Phenylacetyl-CoA and L-glutamine react to form phenylacetylglutamine and coenzyme A. The enzyme (glutamine N-acetyl transferase) that catalyzes this reaction has been purified from human liver mitochondria and shown to be a polypeptide species distinct from glycine-N-acyltransferase. Phenylacetylglutamine is a major nitrogenous metabolite that accumulates in uremia (PMID: 2791363, 8972626). It has been shown that over 50\\\% of urine phenylacetylglutamine may be derived from kidney conjugation of free plasma phenylacetic acid and/or from the kidneys preferential filtration of conjugated phenylacetic acid (PMID: 6420430). Phenylacetylglutamine is a microbial metabolite found in Christensenellaceae, Lachnospiraceae and Ruminococcaceae (PMID: 26241311).
Phenylacetylglutamine is a product formed by the conjugation of phenylacetate and glutamine. Technically it is the amino acid acetylation product of phenylacetate (or phenylbutyrate after beta-oxidation). Phenylacetylglutamine is a normal constituent of human urine, but other mammals including the dog, cat, rat, monkey, sheep and horse do not excrete this compound. Phenylacetyl CoA and glutamine react to form phenylacetyl glutamine and Coenzyme A. The enzyme (Glutamine N-acetyl transferase) that catalyzes this reaction has been purified from human liver mitochondria and shown to be a distinct polypeptide species from glycine-N-acyltransferase. Phenylacetylglutamine is a major nitrogenous metabolite that accumulates in uremia. (PMID: 2791363; PMID: 8972626). It has been shown that over 50\\\% of urine phenylacetylglutamine may be derived from kidney conjugation of free plasma phenylacetic acid and/or from the kidneys preferential filtration of conjugated phenylacetic acid (PMID: 6420430)
Phenylacetylglutamine is a colonic microbial metabolite from amino acid fermentation.

同义名列表

19 个代谢物同义名

(2S)-5-amino-5-oxo-2-[(2-phenylacetyl)amino]pentanoic acid; (2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid; N-[(4-Hydroxyphenyl)acetyl]glutamic acid; L-N(sup 2)-(Phenylacetyl)glutamine; N(2)-(2-Phenylacetyl)-L-glutamine; alpha-N-Phenylacetyl-L-glutamine; N2-(2-Phenylacetyl)-L-glutamine; N(2)-(Phenylacetyl)-L-glutamine; alpha-N-Phenylacetylglutamine; N2-(Phenylacetyl)-L-glutamine; a-N-Phenylacetyl-L-glutamine; Α-N-phenylacetyl-L-glutamine; N(2)-phenylacetylglutamine; α-N-Phenylacetylglutamine; Phenylacetyl-L-glutamine; N-Phenylacetylglutamine; Phenylacetylglutamine; Phenylacetylglutamine; NSC 203800



数据库引用编号

21 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

4 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(4)

  • Phenylacetate Metabolism: Adenosine triphosphate + Coenzyme A + Phenylacetic acid ⟶ Adenosine monophosphate + Phenylacetyl-CoA + Pyrophosphate
  • Phenylacetate Metabolism: Adenosine triphosphate + Coenzyme A + Phenylacetic acid ⟶ Adenosine monophosphate + Phenylacetyl-CoA + Pyrophosphate
  • Phenylacetate Metabolism: Adenosine triphosphate + Coenzyme A + Phenylacetic acid ⟶ Adenosine monophosphate + Phenylacetyl-CoA + Pyrophosphate
  • Phenylacetate Metabolism: Adenosine triphosphate + Coenzyme A + Phenylacetic acid ⟶ Adenosine monophosphate + Phenylacetyl-CoA + Pyrophosphate

PharmGKB(0)

3 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

  • Xiaofeng Chen, Hua Zhang, Sichong Ren, Yangnan Ding, Naznin Sultana Remex, Md Shenuarin Bhuiyan, Jiahua Qu, Xiaoqiang Tang. Gut microbiota and microbiota-derived metabolites in cardiovascular diseases. Chinese medical journal. 2023 Jul; ?(?):. doi: 10.1097/cm9.0000000000002206. [PMID: 37442759]
  • J Xu, M Cai, Z Wang, Q Chen, X Han, J Tian, S Jin, Z Yan, Y Li, B Lu, H Lu. Phenylacetylglutamine as a novel biomarker of type 2 diabetes with distal symmetric polyneuropathy by metabolomics. Journal of endocrinological investigation. 2022 Oct; ?(?):. doi: 10.1007/s40618-022-01929-w. [PMID: 36282471]
  • Xiao Zong, Qin Fan, Qian Yang, Roubai Pan, Lingfang Zhuang, Rong Tao. Phenylacetylglutamine as a risk factor and prognostic indicator of heart failure. ESC heart failure. 2022 08; 9(4):2645-2653. doi: 10.1002/ehf2.13989. [PMID: 35624536]
  • Mitchelle Katemauswa, Ekram Hossain, Zongyuan Liu, Mahbobeh Lesani, Adwaita R Parab, Danya A Dean, Laura-Isobel McCall. Enabling Quantitative Analysis of Surface Small Molecules for Exposomics and Behavioral Studies. Journal of the American Society for Mass Spectrometry. 2022 Mar; 33(3):412-419. doi: 10.1021/jasms.1c00263. [PMID: 35084848]
  • Quentin Leyrolle, Renata Cserjesi, Romane Demeure, Audrey M Neyrinck, Camille Amadieu, Julie Rodriguez, Olli Kärkkäinen, Kati Hanhineva, Nicolas Paquot, Miriam Cnop, Patrice D Cani, Jean-Paul Thissen, Laure B Bindels, Olivier Klein, Olivier Luminet, Nathalie M Delzenne. Microbiota and Metabolite Profiling as Markers of Mood Disorders: A Cross-Sectional Study in Obese Patients. Nutrients. 2021 Dec; 14(1):. doi: 10.3390/nu14010147. [PMID: 35011021]
  • Xiaofeng Wang, Jack Tseng, Carmen Mak, Nagaraju Poola, Regis A Vilchez. Exposures of Phenylacetic Acid and Phenylacetylglutamine Across Different Subpopulations and Correlation with Adverse Events. Clinical pharmacokinetics. 2021 12; 60(12):1557-1567. doi: 10.1007/s40262-021-01047-5. [PMID: 34125423]
  • Robert D Mair, Seolhyun Lee, Natalie S Plummer, Tammy L Sirich, Timothy W Meyer. Impaired Tubular Secretion of Organic Solutes in Advanced Chronic Kidney Disease. Journal of the American Society of Nephrology : JASN. 2021 11; 32(11):2877-2884. doi: 10.1681/asn.2021030336. [PMID: 34408065]
  • Yang Liu, Shaoyan Liu, Zhizhuang Zhao, Xiang Song, Haixian Qu, Hongbin Liu. Phenylacetylglutamine is associated with the degree of coronary atherosclerotic severity assessed by coronary computed tomographic angiography in patients with suspected coronary artery disease. Atherosclerosis. 2021 09; 333(?):75-82. doi: 10.1016/j.atherosclerosis.2021.08.029. [PMID: 34438323]
  • Filip Ottosson, Louise Brunkwall, Einar Smith, Marju Orho-Melander, Peter M Nilsson, Céline Fernandez, Olle Melander. The gut microbiota-related metabolite phenylacetylglutamine associates with increased risk of incident coronary artery disease. Journal of hypertension. 2020 12; 38(12):2427-2434. doi: 10.1097/hjh.0000000000002569. [PMID: 32665522]
  • Kiana Ashley West, Chidimma Kanu, Tanya Maric, Julie Anne Kathryn McDonald, Jeremy K Nicholson, Jia V Li, Mark R Johnson, Elaine Holmes, Makrina D Savvidou. Longitudinal metabolic and gut bacterial profiling of pregnant women with previous bariatric surgery. Gut. 2020 08; 69(8):1452-1459. doi: 10.1136/gutjnl-2019-319620. [PMID: 31964751]
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  • Fernando Andrade, Isidro Vitoria, Elena Martín Hernández, Guillem Pintos-Morell, Patricia Correcher, Rocío Puig-Piña, Pilar Quijada-Fraile, Luis Peña-Quintana, Ana Mª Marquez, Olatz Villate, Mª Teresa García Silva, Javier de Las Heras, Leticia Ceberio, Esmeralda Rodrigues, Teresa Almeida Campos, Raquel Yahyaoui, Javier Blasco, Inmaculada Vives-Piñera, David Gil, Mireia Del Toro, Mónica Ruiz-Pons, Elvira Cañedo, Miguel Angel Barba Romero, Mª Concepción García-Jiménez, Luis Aldámiz-Echevarría. Quantification of urinary derivatives of Phenylbutyric and Benzoic acids by LC-MS/MS as treatment compliance biomarkers in Urea Cycle disorders. Journal of pharmaceutical and biomedical analysis. 2019 Nov; 176(?):112798. doi: 10.1016/j.jpba.2019.112798. [PMID: 31394303]
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  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Sheldon C Leong, Justin N Sao, Abigail Taussig, Natalie S Plummer, Timothy W Meyer, Tammy L Sirich. Residual Function Effectively Controls Plasma Concentrations of Secreted Solutes in Patients on Twice Weekly Hemodialysis. Journal of the American Society of Nephrology : JASN. 2018 07; 29(7):1992-1999. doi: 10.1681/asn.2018010081. [PMID: 29728422]
  • Mai Hazekawa, Kazuhiko Ono, Takuya Nishinakagawa, Tomoyo Kawakubo-Yasukochi, Manabu Nakashima. In Vitro Anti-inflammatory Effects of the Phenylbutyric Acid Metabolite Phenylacetyl Glutamine. Biological & pharmaceutical bulletin. 2018 Jun; 41(6):961-966. doi: 10.1248/bpb.b17-00799. [PMID: 29526885]
  • R Todd Stravitz, Michelle Gottfried, Valerie Durkalski, Robert J Fontana, A James Hanje, David Koch, Bilal Hameed, Daniel Ganger, Ram M Subramanian, Stan Bukofzer, William R Ravis, Kristen Clasen, Averell Sherker, Lanna Little, William M Lee. Safety, tolerability, and pharmacokinetics of l-ornithine phenylacetate in patients with acute liver injury/failure and hyperammonemia. Hepatology (Baltimore, Md.). 2018 03; 67(3):1003-1013. doi: 10.1002/hep.29621. [PMID: 29080224]
  • Hai-Tao Yu, Xiao-Yi Fu, Bin Xu, Li-Li Zuo, Hong-Bo Ma, Shu-Ran Wang. Untargeted metabolomics approach (UPLC-Q-TOF-MS) explores the biomarkers of serum and urine in overweight/obese young men. Asia Pacific journal of clinical nutrition. 2018 ; 27(5):1067-1076. doi: 10.6133/apjcn.052018.07. [PMID: 30272855]
  • Tariq Shafi, Tammy L Sirich, Timothy W Meyer, Thomas H Hostetter, Natalie S Plummer, Seungyoung Hwang, Michal L Melamed, Tanushree Banerjee, Josef Coresh, Neil R Powe. Results of the HEMO Study suggest that p-cresol sulfate and indoxyl sulfate are not associated with cardiovascular outcomes. Kidney international. 2017 12; 92(6):1484-1492. doi: 10.1016/j.kint.2017.05.012. [PMID: 28739139]
  • Yi Jiang, Mohammed Almannai, V Reid Sutton, Qin Sun, Sarah H Elsea. Quantitation of phenylbutyrate metabolites by UPLC-MS/MS demonstrates inverse correlation of phenylacetate:phenylacetylglutamine ratio with plasma glutamine levels. Molecular genetics and metabolism. 2017 11; 122(3):39-45. doi: 10.1016/j.ymgme.2017.08.011. [PMID: 28888854]
  • Enrique Almanza-Aguilera, Mireia Urpi-Sarda, Rafael Llorach, Rosa Vázquez-Fresno, Mar Garcia-Aloy, Francesc Carmona, Alex Sanchez, Francisco Madrid-Gambin, Ramon Estruch, Dolores Corella, Cristina Andres-Lacueva. Microbial metabolites are associated with a high adherence to a Mediterranean dietary pattern using a 1H-NMR-based untargeted metabolomics approach. The Journal of nutritional biochemistry. 2017 10; 48(?):36-43. doi: 10.1016/j.jnutbio.2017.06.001. [PMID: 28692847]
  • Ruben Poesen, Kathleen Claes, Pieter Evenepoel, Henriette de Loor, Patrick Augustijns, Dirk Kuypers, Björn Meijers. Microbiota-Derived Phenylacetylglutamine Associates with Overall Mortality and Cardiovascular Disease in Patients with CKD. Journal of the American Society of Nephrology : JASN. 2016 Nov; 27(11):3479-3487. doi: 10.1681/asn.2015121302. [PMID: 27230658]
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