Ophthalmic acid (BioDeep_00000003000)

 

Secondary id: BioDeep_00000320016

human metabolite Endogenous natural product BioNovoGene_Lab2019


代谢物信息卡片


(2S)-2-amino-4-{[(1S)-1-[(carboxymethyl)carbamoyl]propyl]carbamoyl}butanoic acid

化学式: C11H19N3O6 (289.1274)
中文名称: 眼酸
谱图信息: 最多检出来源 Viridiplantae(plant) 23.28%

分子结构信息

SMILES: CCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N
InChI: InChI=1S/C11H19N3O6/c1-2-7(10(18)13-5-9(16)17)14-8(15)4-3-6(12)11(19)20/h6-7H,2-5,12H2,1H3,(H,13,18)(H,14,15)(H,16,17)(H,19,20)/t6-,7-/m0/s1

描述信息

Ophthalmic acid, also known as ophthalmate, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Ophthalmic acid is a very strong basic compound (based on its pKa). Ophthalmic acid is an L-glutamine derivative in which L-glutamine is substituted by a 1--1-oxobutan-2-yl at the terminal amino nitrogen atom. Ophthalmic acid is an analogue of glutathione isolated from crystalline lens.
Ophthalmic acid is an analogue of glutathione isolated from crystalline lens. [HMDB]

同义名列表

11 个代谢物同义名

(2S)-2-amino-4-{[(1S)-1-[(carboxymethyl)carbamoyl]propyl]carbamoyl}butanoic acid; L-gamma-Glutamyl-L-alpha-aminobutyrylglycine; L-gamma-Glutamyl-(2S)-2-aminobutanoylglycine; gamma-Glutamyl-alpha-amino-n-butyrylglycine; L-γ-Glutamyl-(2S)-2-aminobutanoylglycine; γ-Glutamyl-α-amino-n-butyrylglycine; gamma-Glu-alpha-aminobutyryl-gly; ophthalmic acid; SCHEMBL12181828; Ophthalmate; Ophthalmic acid



数据库引用编号

15 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(1)

Plant Reactome(0)

INOH(0)

PlantCyc(3)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

11 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 7 ABCB1, GLO1, GSTP1, HIF1A, MYC, RIDA, SLC9A1
Endosome membrane 1 ADRB2
Endoplasmic reticulum membrane 2 PROS1, SLC7A11
Nucleus 5 ADRB2, GSTP1, HIF1A, MYC, RIDA
cytosol 8 GCLC, GCLM, GLO1, GSR, GSS, GSTP1, HIF1A, RIDA
nuclear body 1 HIF1A
nucleoplasm 4 GLO1, HIF1A, MYC, SLC9A1
RNA polymerase II transcription regulator complex 1 HIF1A
Cell membrane 6 ABCB1, ABCC1, ADRB2, SLC7A11, SLC9A1, TNF
lamellipodium 1 SLC9A1
Multi-pass membrane protein 5 ABCB1, ABCC1, ADRB2, SLC7A11, SLC9A1
cell surface 4 ABCB1, SLC7A11, SLC9A1, TNF
Golgi apparatus 1 ADRB2
Golgi membrane 2 INS, PROS1
mitochondrial inner membrane 1 ATP5ME
neuronal cell body 1 TNF
Lysosome 2 ADRB2, SGSH
endosome 1 ADRB2
plasma membrane 8 ABCB1, ABCC1, ADRB2, GLO1, PROS1, SLC7A11, SLC9A1, TNF
Membrane 6 ABCB1, ABCC1, ADRB2, MYC, SLC7A11, SLC9A1
apical plasma membrane 4 ABCB1, ABCC1, ADRB2, SLC9A1
basolateral plasma membrane 3 ABCC1, SLC7A11, SLC9A1
extracellular exosome 10 ABCB1, ABCC1, GLO1, GSR, GSS, GSTP1, PROS1, RIDA, SGSH, SLC9A1
endoplasmic reticulum 1 PROS1
extracellular space 4 GSTP1, INS, PROS1, TNF
lysosomal lumen 1 SGSH
perinuclear region of cytoplasm 1 SLC9A1
intercalated disc 1 SLC9A1
mitochondrion 6 ATP5ME, GCLC, GSR, GSTP1, RIDA, SLC9A1
protein-containing complex 2 HIF1A, MYC
Single-pass type I membrane protein 1 SLC7A11
Secreted 3 INS, PROS1, TRH
extracellular region 5 GSTP1, INS, PROS1, TNF, TRH
mitochondrial matrix 2 GSR, RIDA
motile cilium 1 HIF1A
external side of plasma membrane 2 GSR, TNF
T-tubule 1 SLC9A1
nucleolus 1 MYC
axon cytoplasm 1 HIF1A
Early endosome 1 ADRB2
apical part of cell 1 SLC7A11
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 GSTP1
Apical cell membrane 1 ABCB1
Membrane raft 2 SLC9A1, TNF
focal adhesion 1 SLC9A1
Peroxisome 1 RIDA
secretory granule 1 TRH
lateral plasma membrane 2 ABCC1, SLC7A11
nuclear speck 1 HIF1A
receptor complex 1 ADRB2
chromatin 2 HIF1A, MYC
phagocytic cup 1 TNF
brush border membrane 1 SLC7A11
Nucleus, nucleolus 1 MYC
blood microparticle 1 PROS1
Basolateral cell membrane 2 SLC7A11, SLC9A1
Cell projection, microvillus membrane 1 SLC7A11
microvillus membrane 1 SLC7A11
nuclear envelope 1 MYC
endosome lumen 1 INS
Nucleus, nucleoplasm 1 MYC
Nucleus speckle 1 HIF1A
euchromatin 1 HIF1A
basal plasma membrane 1 ABCC1
ficolin-1-rich granule lumen 1 GSTP1
secretory granule lumen 2 GSTP1, INS
Golgi lumen 2 INS, PROS1
endoplasmic reticulum lumen 1 INS
platelet alpha granule lumen 1 PROS1
transport vesicle 1 INS
RNA polymerase II transcription repressor complex 1 MYC
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
neuronal dense core vesicle 1 ADRB2
clathrin-coated endocytic vesicle membrane 1 ADRB2
external side of apical plasma membrane 1 ABCB1
Rough endoplasmic reticulum 1 MYC
proton-transporting ATP synthase complex 1 ATP5ME
astrocyte projection 1 SLC7A11
proton-transporting ATP synthase complex, coupling factor F(o) 1 ATP5ME
Myc-Max complex 1 MYC
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
TRAF2-GSTP1 complex 1 GSTP1
cation-transporting ATPase complex 1 SLC9A1
glutamate-cysteine ligase complex 2 GCLC, GCLM
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
nucleoplasmic reticulum 1 MYC


文献列表

  • Carmen Priolo, Damir Khabibullin, Ed Reznik, Harilaos Filippakis, Barbara Ogórek, Taylor R Kavanagh, Julie Nijmeh, Zachary T Herbert, John M Asara, David J Kwiatkowski, Chin-Lee Wu, Elizabeth P Henske. Impairment of gamma-glutamyl transferase 1 activity in the metabolic pathogenesis of chromophobe renal cell carcinoma. Proceedings of the National Academy of Sciences of the United States of America. 2018 07; 115(27):E6274-E6282. doi: 10.1073/pnas.1710849115. [PMID: 29891694]
  • Luigi Servillo, Domenico Castaldo, Alfonso Giovane, Rosario Casale, Nunzia D'Onofrio, Domenico Cautela, Maria Luisa Balestrieri. Ophthalmic acid is a marker of oxidative stress in plants as in animals. Biochimica et biophysica acta. General subjects. 2018 Apr; 1862(4):991-998. doi: 10.1016/j.bbagen.2018.01.015. [PMID: 29413907]
  • Jaeyong Lee, Eun Sil Kang, Sho Kobayashi, Takujiro Homma, Hideyo Sato, Han Geuk Seo, Junichi Fujii. The viability of primary hepatocytes is maintained under a low cysteine-glutathione redox state with a marked elevation in ophthalmic acid production. Experimental cell research. 2017 12; 361(1):178-191. doi: 10.1016/j.yexcr.2017.10.017. [PMID: 29079265]
  • Sho Kobayashi, Jaeyong Lee, Toshifumi Takao, Junichi Fujii. Increased ophthalmic acid production is supported by amino acid catabolism under fasting conditions in mice. Biochemical and biophysical research communications. 2017 09; 491(3):649-655. doi: 10.1016/j.bbrc.2017.07.149. [PMID: 28757411]
  • Gurnit Kaur, Elaine M Leslie, Holly Tillman, William M Lee, Diane P Swanlund, Constantine J Karvellas. Detection of Ophthalmic Acid in Serum from Acetaminophen-Induced Acute Liver Failure Patients Is More Frequent in Non-Survivors. PloS one. 2015; 10(9):e0139299. doi: 10.1371/journal.pone.0139299. [PMID: 26407170]
  • Simon A W G Dello, Evelien P J G Neis, Mechteld C de Jong, Hans M H van Eijk, Cécile H Kicken, Steven W M Olde Damink, Cornelis H C Dejong. Systematic review of ophthalmate as a novel biomarker of hepatic glutathione depletion. Clinical nutrition (Edinburgh, Scotland). 2013 Jun; 32(3):325-30. doi: 10.1016/j.clnu.2012.10.008. [PMID: 23182341]
  • Suzanne Geenen, James W T Yates, J Gerry Kenna, Frederic Y Bois, Ian D Wilson, Hans V Westerhoff. Multiscale modelling approach combining a kinetic model of glutathione metabolism with PBPK models of paracetamol and the potential glutathione-depletion biomarkers ophthalmic acid and 5-oxoproline in humans and rats. Integrative biology : quantitative biosciences from nano to macro. 2013 Jun; 5(6):877-88. doi: 10.1039/c3ib20245c. [PMID: 23632663]
  • Simon A W G Dello, Hans M H van Eijk, Evelien P J G Neis, Mechteld C de Jong, Steven W M Olde Damink, Cornelis H C Dejong. Ophthalmate detection in human plasma with LC-MS-MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Aug; 903(?):1-6. doi: 10.1016/j.jchromb.2012.06.023. [PMID: 22831884]
  • Suzanne Geenen, Filippos Michopoulos, J Gerry Kenna, Kyle L Kolaja, Hans V Westerhoff, Ian Wilson. HPLC-MS/MS methods for the quantitative analysis of ophthalmic acid in rodent plasma and hepatic cell line culture medium. Journal of pharmaceutical and biomedical analysis. 2011 Apr; 54(5):1128-35. doi: 10.1016/j.jpba.2010.11.038. [PMID: 21176868]
  • Shujie Shi, Sylvia Notenboom, Mark E Dumont, Nazzareno Ballatori. Identification of human gene products containing Pro-Pro-x-Tyr (PY) motifs that enhance glutathione and endocytotic marker uptake in yeast. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2010; 25(2-3):293-306. doi: 10.1159/000276570. [PMID: 20110690]
  • Rajan S Kombu, Guo-Fang Zhang, Rime Abbas, John J Mieyal, Vernon E Anderson, Joanne K Kelleher, Juan R Sanabria, Henri Brunengraber. Dynamics of glutathione and ophthalmate traced with 2H-enriched body water in rats and humans. American journal of physiology. Endocrinology and metabolism. 2009 Jul; 297(1):E260-9. doi: 10.1152/ajpendo.00080.2009. [PMID: 19401458]
  • Lee-Sun New, Eric C Y Chan. Evaluation of BEH C18, BEH HILIC, and HSS T3 (C18) column chemistries for the UPLC-MS-MS analysis of glutathione, glutathione disulfide, and ophthalmic acid in mouse liver and human plasma. Journal of chromatographic science. 2008 Mar; 46(3):209-14. doi: 10.1093/chromsci/46.3.209. [PMID: 18334086]
  • Tomoyoshi Soga, Richard Baran, Makoto Suematsu, Yuki Ueno, Satsuki Ikeda, Tadayuki Sakurakawa, Yuji Kakazu, Takamasa Ishikawa, Martin Robert, Takaaki Nishioka, Masaru Tomita. Differential metabolomics reveals ophthalmic acid as an oxidative stress biomarker indicating hepatic glutathione consumption. The Journal of biological chemistry. 2006 Jun; 281(24):16768-76. doi: 10.1074/jbc.m601876200. [PMID: 16608839]
  • C S Huang, L S Chang, M E Anderson, A Meister. Catalytic and regulatory properties of the heavy subunit of rat kidney gamma-glutamylcysteine synthetase. The Journal of biological chemistry. 1993 Sep; 268(26):19675-80. doi: . [PMID: 8103521]
  • M Orlowski, S Wilk. Synthesis of ophthalmic acid in liver and kidney in vivo. The Biochemical journal. 1978 Feb; 170(2):415-9. doi: 10.1042/bj1700415. [PMID: 637852]