gamma-Glutamylphenylalanine (BioDeep_00000018623)
Secondary id: BioDeep_00000229663
human metabolite PANOMIX_OTCML-2023 Endogenous
代谢物信息卡片
化学式: C14H18N2O5 (294.1215658)
中文名称: γ-谷氨酰苯丙氨酸
谱图信息:
最多检出来源 Homo sapiens(feces) 40.83%
Last reviewed on 2024-09-14.
Cite this Page
gamma-Glutamylphenylalanine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/gamma-glutamylphenylalanine (retrieved
2024-11-25) (BioDeep RN: BioDeep_00000018623). 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(C(=O)O)NC(=O)CCC(C(=O)O)N
InChI: InChI=1S/C14H18N2O5/c15-10(13(18)19)6-7-12(17)16-11(14(20)21)8-9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,17)(H,18,19)(H,20,21)/t10-,11-/m0/s1
描述信息
gamma-Glutamylphenylalanine is a dipeptide composed of gamma-glutamate and phenylalanine, and is a proteolytic breakdown product of larger proteins. It is probably formed by transpeptidation between glutathione and the corresponding amino acid, catalyzed by gamma-glutamyl transpeptidase (PMID: 237763). gamma-Glutamylphenylalanine belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylphenylalanine is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. It can be detected in the urine of patients with phenylketonuria, which is a human genetic disorder due to the lack of phenylalanine hydroxylase to metabolize phenylalanine to tyrosine (Wikipedia). gamma-Glutamylphenylalanine is found in adzuki bean, onion (Allium cepa), garlic (Allium sativum), and soybean.
γ-Glu-Phe (γ-Glutamylphenylalanine) is synthesized by Bacillus amyloliquefaciens (GBA) and Aspergillus oryzae (GAO). γ-Glu-Phe or the post-enzymatic reaction mixture enhances the umami intensity of commercial soy sauce and model chicken broth[1].
γ-Glu-Phe (γ-Glutamylphenylalanine) is synthesized by Bacillus amyloliquefaciens (GBA) and Aspergillus oryzae (GAO). γ-Glu-Phe or the post-enzymatic reaction mixture enhances the umami intensity of commercial soy sauce and model chicken broth[1].
同义名列表
35 个代谢物同义名
(2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid; (2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoate; N-L-gamma-Glutamyl-3-phenyl-L-alanine; N-L-gamma-Glutamyl-L-phenylalanine; N-gamma-L-Glutamyl-L-phenylalanine; N-L-Γ-glutamyl-3-phenyl-L-alanine; N-(gamma-L-Glutamyl)phenylalanine; N-L-g-Glutamyl-3-phenyl-L-alanine; gamma-L-Glutamyl-L-phenylalanine; L-gamma-Glutamyl-L-phenylalanine; N-L-gamma-Glutamylphenylalanine; N-L-g-Glutamyl-L-phenylalanine; N-γ-L-Glutamyl-L-phenylalanine; N-L-Γ-glutamyl-L-phenylalanine; N-(g-L-Glutamyl)phenylalanine; N-(Γ-L-glutamyl)phenylalanine; N-gamma-Glutamylphenylalanine; γ-L-Glutamyl-L-phenylalanine; L-Γ-glutamyl-L-phenylalanine; L-g-Glutamyl-L-phenylalanine; N-L-γ-Glutamylphenylalanine; gamma-Glutamylphenylalanine; N-γ-Glutamylphenylalanine; Γ-glutamylphenylalanine; g-Glutamylphenylalanine; H-gamma-glu-phe-oh; gamma-L-Glu-L-Phe; L-gamma-Glu-L-phe; H-γ-Glu-Phe-OH; L-Γ-glu-L-phe; γ-L-Glu-L-Phe; L-g-Glu-L-phe; gamma-Glu-phe; g-Glu-Phe; γ-Glu-Phe
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:89582
- PubChem: 111299
- HMDB: HMDB0000594
- foodb: FDB112161
- chemspider: 99868
- CAS: 7432-24-8
- PMhub: MS000009778
- RefMet: gamma-Glutamylphenylalanine
- medchemexpress: HY-101399
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)
5 个相关的物种来源信息
- 4679 - Allium cepa: 10.1515/BCHM2.1960.322.1.8
- 4682 - Allium sativum: 10.1016/0031-9422(92)83283-5
- 3708 - Brassica napus: 10.3389/FNUT.2022.822033
- 9606 - Homo sapiens: -
- 157791 - Vigna radiata: 10.1016/0031-9422(86)88023-2
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
- Yu Geon Lee, Jeong-Yong Cho, Eom Ji Hwang, Tae-Il Jeon, Jae-Hak Moon. Glu-Phe from onion (Allium Cepa L.) attenuates lipogenesis in hepatocytes.
Bioscience, biotechnology, and biochemistry.
2017 Jul; 81(7):1409-1416. doi:
10.1080/09168451.2017.1303358
. [PMID: 28345482] - Chiara Bottesini, Tullia Tedeschi, Arnaldo Dossena, Stefano Sforza. Enzymatic production and degradation of cheese-derived non-proteolytic aminoacyl derivatives.
Amino acids.
2014 Feb; 46(2):441-7. doi:
10.1007/s00726-013-1637-3
. [PMID: 24337832] - Rongli Sun, Juan Zhang, Mengzhen Xiong, Yue Chen, Lihong Yin, Yuepu Pu. Metabonomics biomarkers for subacute toxicity screening for benzene exposure in mice.
Journal of toxicology and environmental health. Part A.
2012; 75(18):1163-73. doi:
10.1080/15287394.2012.699858
. [PMID: 22891888] - J P Kamerling, G J Aarsen, M Duran, P K de Bree, F J van Sprang, S K Wadman. Chromatographic determination and mass spectrometric identification of gamma-glutamylphenylalanine, a urinary constituent in phenylketonuria.
Clinica chimica acta; international journal of clinical chemistry.
1980 Mar; 102(2-3):137-45. doi:
10.1016/0009-8981(80)90026-1
. [PMID: 7371187]