Phenylacetylglycine (BioDeep_00000002795)

 

Secondary id: BioDeep_00000405375

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


[(Phenylacetyl)amino]acetic acid

化学式: C10H11NO3 (193.0738896)
中文名称: 苯乙酰甘氨酸, 苯乙酰甘氨酸, 苯乙酰甘氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.11%

分子结构信息

SMILES: C1=CC=C(C=C1)CC(=O)NCC(=O)O
InChI: InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)

描述信息

Phenylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Phenylacetylglycine or PAG is a glycine conjugate of phenylacetic acid. Phenylacetic acid may arise from exposure to styrene (plastic) or through the consumption of fruits and vegetables. Phenylacetic acid is used in some perfumes, possessing a honey-like odour in low concentrations, and is also used in penicillin G production. PAG is a putative biomarker of phospholipidosis. Urinary PAG is elevated in animals exhibiting abnormal phospholipid accumulation in many tissues and may thus be useful as a surrogate biomarker for phospholipidosis. (PMID: 15764292) The presence of phenylacetylglycine in urine has been confirmed for dogs, rats and mice. However, the presence of this compound in human urine is controversial. GC-MS studies have not found this compound (PMID: 7492634) while NMR studies claimed to have identified it (PMID: 21167146). It appears that phenylacetylglycine may sometimes be mistaken for phenylacetylglutamine via NMR.
Phenylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:
Phenylacetylglycine is a gut microbial metabolite that can activate β2AR. Phenylacetylglycine protects against cardiac injury caused by ischemia/reperfusion[1].
Phenylacetylglycine is a gut microbial metabolite that can activate β2AR. Phenylacetylglycine protects against cardiac injury caused by ischemia/reperfusion[1].

同义名列表

18 个代谢物同义名

[(Phenylacetyl)amino]acetic acid; ((Phenylacetyl)amino)acetic acid; 2-(2-phenylacetamido)acetic acid; [(Phenylacetyl)amino]acetate; N-(Phenylacetyl)-glycine; N-(Phenylacetyl)glycine; N-Phenylacetylglycine; Phenylacetyl glycine; Phenylacetylglycine; N-Phenacetylglycine; Phenacetylglycine; Phenaceturic acid; Phenacetic acid; Phenaceturate; Phenacetate; PAA; PAG; Phenylacetylglycine



数据库引用编号

26 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

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Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

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PharmGKB(0)

6 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

  • Ming-Yuan Xu, Ying-Jian Sun, Pan Wang, Lin Yang, Yi-Jun Wu. Metabolomic biomarkers in urine of rats following long-term low-dose exposure of cadmium and/or chlorpyrifos. Ecotoxicology and environmental safety. 2020 Jun; 195(?):110467. doi: 10.1016/j.ecoenv.2020.110467. [PMID: 32182532]
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  • Zhenzhao Wang, Rui Xu, Guiping Shen, Jianghua Feng. Metabolic Response in Rabbit Urine to Occurrence and Relief of Unilateral Ureteral Obstruction. Journal of proteome research. 2018 09; 17(9):3184-3194. doi: 10.1021/acs.jproteome.8b00304. [PMID: 30024170]
  • Gregorio Peron, Stefano Dall'Acqua, Stefania Sut. Supplementation with resveratrol as Polygonum cuspidatum Sieb. et Zucc. extract induces changes in the excretion of urinary markers associated to aging in rats. Fitoterapia. 2018 Sep; 129(?):154-161. doi: 10.1016/j.fitote.2018.06.022. [PMID: 29959053]
  • Ning Ma, Yajun Yang, Xiwang Liu, Xiaojun Kong, Shihong Li, Zhe Qin, Zenghua Jiao, Jianyong Li. UPLC-Q-TOF/MS-based metabonomic studies on the intervention effects of aspirin eugenol ester in atherosclerosis hamsters. Scientific reports. 2017 09; 7(1):10544. doi: 10.1038/s41598-017-11422-7. [PMID: 28874840]
  • Nishikant Wase, Boqiang Tu, James W Allen, Paul N Black, Concetta C DiRusso. Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae. Plant physiology. 2017 Aug; 174(4):2146-2165. doi: 10.1104/pp.17.00433. [PMID: 28652262]
  • You Jin Kim, Iksoo Huh, Ji Yeon Kim, Saejong Park, Sung Ha Ryu, Kyu-Bong Kim, Suhkmann Kim, Taesung Park, Oran Kwon. Integration of Traditional and Metabolomics Biomarkers Identifies Prognostic Metabolites for Predicting Responsiveness to Nutritional Intervention against Oxidative Stress and Inflammation. Nutrients. 2017 Mar; 9(3):. doi: 10.3390/nu9030233. [PMID: 28273855]
  • Hidenori Kamiguchi, Mika Murabayashi, Ikuo Mori, Akira Horinouchi, Kazutaka Higaki. Biomarker discovery for drug-induced phospholipidosis: phenylacetylglycine to hippuric acid ratio in urine and plasma as potential markers. Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals. 2017 Mar; 22(2):178-188. doi: 10.1080/1354750x.2016.1252958. [PMID: 27775443]
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  • Hidenori Kamiguchi, Masashi Yamaguchi, Mika Murabayashi, Ikuo Mori, Akira Horinouchi. Method development and validation for simultaneous quantitation of endogenous hippuric acid and phenylacetylglycine in rat urine using liquid chromatography coupled with electrospray ionization tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 Nov; 1035(?):76-83. doi: 10.1016/j.jchromb.2016.09.036. [PMID: 27697729]
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  • Jeeyoun Jung, Youngae Jung, Eun Jung Bang, Sung-il Cho, You-Jin Jang, Jung-Myun Kwak, Do Hyun Ryu, Sungsoo Park, Geum-Sook Hwang. Noninvasive diagnosis and evaluation of curative surgery for gastric cancer by using NMR-based metabolomic profiling. Annals of surgical oncology. 2014 Dec; 21 Suppl 4(?):S736-42. doi: 10.1245/s10434-014-3886-0. [PMID: 25092158]
  • Rune Gangsøy Kristiansen, Christopher F Rose, Ole-Martin Fuskevåg, Hanne Mæhre, Arthur Revhaug, Rajiv Jalan, Lars Marius Ytrebø. L-Ornithine phenylacetate reduces ammonia in pigs with acute liver failure through phenylacetylglycine formation: a novel ammonia-lowering pathway. American journal of physiology. Gastrointestinal and liver physiology. 2014 Nov; 307(10):G1024-31. doi: 10.1152/ajpgi.00244.2014. [PMID: 25258408]
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  • Xiao-Xia Gao, Jie Cui, Xing-Yu Zheng, Zhen-Yu Li, Young-Hae Choi, Yu-Zhi Zhou, Jun-Sheng Tian, Jie Xing, Xiao-Jie Tan, Guan-Hua Du, Xue-Mei Qin. An investigation of the antidepressant action of xiaoyaosan in rats using ultra performance liquid chromatography-mass spectrometry combined with metabonomics. Phytotherapy research : PTR. 2013 Jul; 27(7):1074-85. doi: 10.1002/ptr.4805. [PMID: 22975930]
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  • Yuanyuan Zhang, Fei Li, Andrew D Patterson, Yao Wang, Kristopher W Krausz, Geoffrey Neale, Sarah Thomas, Deepa Nachagari, Peter Vogel, Mary Vore, Frank J Gonzalez, John D Schuetz. Abcb11 deficiency induces cholestasis coupled to impaired β-fatty acid oxidation in mice. The Journal of biological chemistry. 2012 Jul; 287(29):24784-94. doi: 10.1074/jbc.m111.329318. [PMID: 22619174]
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  • Shangshang Zhang, Xinyu Liu, Shuning Zheng, Minyan Jiang, Changying Xin, Xiumei Lu, Famei Li, Zhili Xiong. [Metabonomic study on protective effect of ethanol extracts of drynariae rhizoma on osteoporosis in rats urine by using UPLC-MS/MS]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Mar; 37(5):658-62. doi: NULL. [PMID: 22693913]
  • Guangguo Tan, Wenting Liao, Xin Dong, Genjing Yang, Zhenyu Zhu, Wuhong Li, Yifeng Chai, Ziyang Lou. Metabonomic profiles delineate the effect of traditional Chinese medicine sini decoction on myocardial infarction in rats. PloS one. 2012; 7(4):e34157. doi: 10.1371/journal.pone.0034157. [PMID: 22493681]
  • M T Osorio, A P Moloney, L Brennan, F J Monahan. Authentication of beef production systems using a metabolomic-based approach. Animal : an international journal of animal bioscience. 2012 Jan; 6(1):167-72. doi: 10.1017/s1751731111001418. [PMID: 22436164]
  • Najla Gooda Sahib, Nazamid Saari, Amin Ismail, Alfi Khatib, Fawzi Mahomoodally, Azizah Abdul Hamid. Plants' metabolites as potential antiobesity agents. TheScientificWorldJournal. 2012; 2012(?):436039. doi: 10.1100/2012/436039. [PMID: 22666121]
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  • Takafumi Toyohara, Takehiro Suzuki, Yasutoshi Akiyama, Daisuke Yoshihara, Yoichi Takeuchi, Eikan Mishima, Koichi Kikuchi, Chitose Suzuki, Masayuki Tanemoto, Sadayoshi Ito, Shizuko Nagao, Tomoyoshi Soga, Takaaki Abe. Metabolomic profiling of the autosomal dominant polycystic kidney disease rat model. Clinical and experimental nephrology. 2011 Oct; 15(5):676-687. doi: 10.1007/s10157-011-0467-4. [PMID: 21695416]
  • Jia V Li, Jasmina Saric, Yulan Wang, Jennifer Keiser, Jürg Utzinger, Elaine Holmes. Chemometric analysis of biofluids from mice experimentally infected with Schistosoma mansoni. Parasites & vectors. 2011 Sep; 4(?):179. doi: 10.1186/1756-3305-4-179. [PMID: 21929782]
  • Morten R Clausen, Kirstine L Christensen, Mette S Hedemann, Ying Liu, Stig Purup, Mette Schmidt, Henrik Callesen, Jan Stagsted, Hanne C Bertram. Metabolomic phenotyping of a cloned pig model. BMC physiology. 2011 Aug; 11(?):14. doi: 10.1186/1472-6793-11-14. [PMID: 21859467]
  • Jonathan R Swann, Kieran M Tuohy, Peter Lindfors, Duncan T Brown, Glenn R Gibson, Ian D Wilson, James Sidaway, Jeremy K Nicholson, Elaine Holmes. Variation in antibiotic-induced microbial recolonization impacts on the host metabolic phenotypes of rats. Journal of proteome research. 2011 Aug; 10(8):3590-603. doi: 10.1021/pr200243t. [PMID: 21591676]
  • Peter G Mantle, Andrew W Nicholls, John P Shockcor. H NMR spectroscopy-based metabolomic assessment of uremic toxicity, with toxicological outcomes, in male rats following an acute, mid-life insult from ochratoxin a. Toxins. 2011 06; 3(6):504-19. doi: 10.3390/toxins3060504. [PMID: 22069722]
  • Seok-Min Kang, Jong-Chul Park, Min-Jeong Shin, Hyeran Lee, Jaewon Oh, Do Hyun Ryu, Geum-Sook Hwang, Ji Hyung Chung. ¹H nuclear magnetic resonance based metabolic urinary profiling of patients with ischemic heart failure. Clinical biochemistry. 2011 Mar; 44(4):293-9. doi: 10.1016/j.clinbiochem.2010.11.010. [PMID: 21167146]
  • Jeeyoun Jung, Minhwa Park, Hye Jin Park, Sun Bo Shim, Yang Ha Cho, Jinho Kim, Ho-Sub Lee, Do Hyun Ryu, Donwoong Choi, Geum-Sook Hwang. ¹H NMR-based metabolic profiling of naproxen-induced toxicity in rats. Toxicology letters. 2011 Jan; 200(1-2):1-7. doi: 10.1016/j.toxlet.2010.09.020. [PMID: 20932884]
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  • James M Kinross, Nawar Alkhamesi, Richard H Barton, David B Silk, Ivan K S Yap, Ara W Darzi, Elaine Holmes, Jeremy K Nicholson. Global metabolic phenotyping in an experimental laparotomy model of surgical trauma. Journal of proteome research. 2011 Jan; 10(1):277-87. doi: 10.1021/pr1003278. [PMID: 21105667]
  • Jia V Li, Jasmina Saric, Yulan Wang, Jürg Utzinger, Elaine Holmes, Oliver Balmer. Metabonomic investigation of single and multiple strain Trypanosoma brucei brucei infections. The American journal of tropical medicine and hygiene. 2011 Jan; 84(1):91-8. doi: 10.4269/ajtmh.2011.10-0402. [PMID: 21212208]
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  • Jasmina Saric, Jia V Li, Jonathan R Swann, Jürg Utzinger, Gail Calvert, Jeremy K Nicholson, Stephan Dirnhofer, Maggie J Dallman, Magda Bictash, Elaine Holmes. Integrated cytokine and metabolic analysis of pathological responses to parasite exposure in rodents. Journal of proteome research. 2010 May; 9(5):2255-64. doi: 10.1021/pr901019z. [PMID: 20092362]
  • Jun-Fang Wu, Elaine Holmes, Jian Xue, Shu-Hua Xiao, Burton H Singer, Hui-Ru Tang, Jürg Utzinger, Yu-Lan Wang. Metabolic alterations in the hamster co-infected with Schistosoma japonicum and Necator americanus. International journal for parasitology. 2010 May; 40(6):695-703. doi: 10.1016/j.ijpara.2009.11.003. [PMID: 19951707]
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