Cysteinylglycine (BioDeep_00000001313)

 

Secondary id: BioDeep_00000400334, BioDeep_00000415888, BioDeep_00000897262

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid

化学式: C5H10N2O3S (178.0412)
中文名称: 半胱氨酰甘氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 34.72%

Reviewed

Last reviewed on 2024-07-02.

Cite this Page

Cysteinylglycine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/cysteinylglycine (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000001313). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(C(C(=O)NCC(=O)O)N)S
InChI: InChI=1S/C5H10N2O3S/c6-3(2-11)5(10)7-1-4(8)9/h3,11H,1-2,6H2,(H,7,10)(H,8,9)

描述信息

Cysteinylglycine is a naturally occurring dipeptide. It is derived from the breakdown of glutathione (a tripeptide). In plasma, cysteinylglycine is in a reduced, oxidized and protein-bound form (aminothiol) and interact via redox and disulphide exchange reactions, in a dynamic system referred to as redox thiol status. (PMID 8642471) Spermatozoa of sub fertile men contain significantly higher thiol concentrations as compared with those of fertile men. The detrimental effect on embryo quality of a high homocysteine (Hcy, another member of the thiol group) concentration in the ejaculate and in follicular fluid is intriguing and may suggest that Hcy is inversely associated with fertility outcome. (PMID 16556671) Rheumatoid arthritis (RA) is a chronic inflammatory disease which involves the synovial membrane of multiple diarthroidal joints causing damage to cartilage and bones. The damage process seems to be related to an overproduction of oxygen reactive species inducing an oxidative perturbation with an increase in some oxidized forms (disulfides and protein mixed disulfides) and a decrease in free thiols. (PMID 15895891) Imipenem (thienamycin formamidine), is a broad-spectrum beta-lactam antibiotic, always used in combination with cilastatin in order to avoid the premature breakdown of imipenem by renal tubular dipeptidase. As this dipeptidase also hydrolyzes the glutathione metabolite cysteinylglycine, the therapeutic association of imipenem and cilastatin causes plasma levels of cysteinylglycine to increase significantly, while cysteine levels are decreased and homocysteine levels are unaffected. Therefore, antibiotic treatment using imipenem-cilastatin induces important metabolic changes that should not remain unrecognized. (PMID 15843241) [HMDB]. Cysteinylglycine is found in many foods, some of which are chinese cabbage, wax apple, garden tomato (variety), and japanese pumpkin.
Cysteinylglycine is a naturally occurring dipeptide composed of cysteine and glycine. It is derived from the breakdown of glutathione (a tripeptide). In plasma, cysteinylglycine is in a reduced, oxidized, and protein-bound form (aminothiol) and interacts via redox and disulphide exchange reactions in a dynamic system referred to as redox thiol status (PMID: 8642471). Spermatozoa of sub-fertile men contain significantly higher thiol concentrations as compared with those of fertile men. The detrimental effect on embryo quality of a high homocysteine (Hcy) concentration in the ejaculate and in the follicular fluid is intriguing and may suggest that Hcy is inversely associated with fertility outcome (PMID: 16556671). Rheumatoid arthritis (RA) is a chronic inflammatory disease which involves the synovial membrane of multiple diarthroidal joints causing damage to cartilage and bones. The damage process seems to be related to an overproduction of oxygen reactive species inducing an oxidative perturbation with an increase in some oxidized forms (disulfides and protein mixed disulfides) and a decrease in free thiols (PMID: 15895891). Imipenem (thienamycin formamidine) is a broad-spectrum beta-lactam antibiotic, always used in combination with cilastatin in order to avoid the premature breakdown of imipenem by renal tubular dipeptidase. As this dipeptidase also hydrolyzes the glutathione metabolite cysteinylglycine, the therapeutic association of imipenem and cilastatin causes plasma levels of cysteinylglycine to increase significantly, while cysteine levels are decreased and homocysteine levels are unaffected. Therefore, antibiotic treatment using imipenem-cilastatin induces important metabolic changes that should not remain unrecognized (PMID: 15843241).

L-Cysteinylglycine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=19246-18-5 (retrieved 2024-07-02) (CAS RN: 19246-18-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

21 个代谢物同义名

2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid; Cysteine-glycine dipeptide; Cysteine glycine dipeptide; N-L-Cysteinyl-glycine; N-L-Cysteinylglycine; N-Cysteinyl glycine; N-Cysteinyl-glycine; N-Cysteinylglycine; L-Cysteinylglycine; Cysteinyl-glycine; cysteine-glycine; Cysteinylglycine; C-g Dipeptide; CG Dipeptide; H-Cys-Gly-OH; L-Cys-gly; Cys-gly; CG; Cysteinylglycine; Cys-Gly; Cys-Gly



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

40 个相关的代谢反应过程信息。

Reactome(15)

BioCyc(1)

  • γ-glutamyl cycle: a 5-L-glutamyl-L-amino acid + cysteinylglycine ⟶ a standard α amino acid + glutathione

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(22)

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。

亚细胞结构定位 关联基因列表
Cytoplasm 6 ALB, ANPEP, CAT, CBS, CNDP2, HPGDS
Peripheral membrane protein 1 CYP1B1
Endoplasmic reticulum membrane 3 CYP1B1, PROS1, SLC7A11
Nucleus 2 ALB, CBS
cytosol 9 ALB, CAT, CBS, CNDP2, GCLM, GPT, GSR, HPGDS, MTHFR
centrosome 1 ALB
nucleoplasm 2 CNDP2, HPGDS
Cell membrane 6 ANPEP, GGT1, GLRA2, SLC15A2, SLC7A11, TNF
Multi-pass membrane protein 3 GLRA2, SLC15A2, SLC7A11
Synapse 1 GLRA2
cell surface 3 SLC7A11, THBS1, TNF
Golgi apparatus 1 ALB
Golgi membrane 2 INS, PROS1
lysosomal membrane 1 ANPEP
neuronal cell body 1 TNF
plasma membrane 7 ANPEP, GGT1, GLRA2, PROS1, SLC15A2, SLC7A11, TNF
Membrane 6 CAT, CYP1B1, GGT1, GLRA2, SLC15A2, SLC7A11
apical plasma membrane 1 SLC15A2
basolateral plasma membrane 1 SLC7A11
extracellular exosome 10 ALB, ANPEP, CAT, CNDP2, GGT1, GPT, GSR, PROS1, SLC15A2, THBS1
endoplasmic reticulum 3 ALB, PROS1, THBS1
extracellular space 8 ALB, ANPEP, GGT1, IL6, INS, PROS1, THBS1, TNF
mitochondrion 3 CAT, CYP1B1, GSR
protein-containing complex 2 ALB, CAT
intracellular membrane-bounded organelle 4 CAT, CYP1B1, GLRA2, HPGDS
Microsome membrane 1 CYP1B1
Single-pass type I membrane protein 1 SLC7A11
Secreted 5 ALB, IL6, INS, PROS1, THBS1
extracellular region 7 ALB, CAT, IL6, INS, PROS1, THBS1, TNF
mitochondrial matrix 2 CAT, GSR
anchoring junction 1 ALB
external side of plasma membrane 4 ANPEP, GSR, THBS1, TNF
Secreted, extracellular space, extracellular matrix 1 THBS1
apical part of cell 1 SLC7A11
recycling endosome 1 TNF
Single-pass type II membrane protein 3 ANPEP, GGT1, TNF
Apical cell membrane 1 SLC15A2
Membrane raft 1 TNF
focal adhesion 1 CAT
GABA-ergic synapse 1 GLRA2
extracellular matrix 1 THBS1
Peroxisome 1 CAT
sarcoplasmic reticulum 1 THBS1
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 THBS1
secretory granule 1 THBS1
lateral plasma membrane 1 SLC7A11
Postsynaptic cell membrane 1 GLRA2
neuron projection 1 GLRA2
ciliary basal body 1 ALB
Cytoplasmic vesicle, phagosome membrane 1 SLC15A2
cell projection 1 GLRA2
phagocytic cup 1 TNF
phagocytic vesicle membrane 1 SLC15A2
centriole 1 ALB
brush border membrane 1 SLC7A11
spindle pole 1 ALB
blood microparticle 2 ALB, PROS1
transmembrane transporter complex 1 GLRA2
Basolateral cell membrane 1 SLC7A11
Cell projection, microvillus membrane 1 SLC7A11
microvillus membrane 1 SLC7A11
endosome lumen 1 INS
chloride channel complex 1 GLRA2
platelet alpha granule 1 THBS1
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
secretory granule membrane 1 ANPEP
Golgi lumen 2 INS, PROS1
endoplasmic reticulum lumen 4 ALB, IL6, INS, THBS1
platelet alpha granule lumen 3 ALB, PROS1, THBS1
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
endoplasmic reticulum-Golgi intermediate compartment 1 ANPEP
postsynaptic specialization membrane 1 GLRA2
astrocyte projection 1 SLC7A11
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
fibrinogen complex 1 THBS1
catalase complex 1 CAT
glycinergic synapse 1 GLRA2
interleukin-6 receptor complex 1 IL6
glutamate-cysteine ligase complex 1 GCLM
ciliary transition fiber 1 ALB
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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