S-Lactoylglutathione (BioDeep_00000001432)

 

Secondary id: BioDeep_00000400310, BioDeep_00001869107

natural product human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid

化学式: C13H21N3O8S (379.1049)
中文名称: S-乳酰谷胱甘肽
谱图信息: 最多检出来源 Homo sapiens(otcml) 26.94%

分子结构信息

SMILES: CC(C(=O)SCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N)O
InChI: InChI=1S/C13H21N3O8S/c1-6(17)13(24)25-5-8(11(21)15-4-10(19)20)16-9(18)3-2-7(14)12(22)23/h6-8,17H,2-5,14H2,1H3,(H,15,21)(H,16,18)(H,19,20)(H,22,23)/t6-,7+,8+/m1/s1

描述信息

S-Lactoylglutathione is a substrate of lactoylglutathione lyase [EC 4.4.1.5] in pyruvate metabolism (KEGG). Another enzyme, glyoxalase I, synthesizes this compound by converting methylglyoxal and reduced glutathione to S-lactoylglutathione. S-D-lactoylglutathione can be hydrolysed by thiolesterases to reduced glutathione and D-lactate but also converted to N-D-lactoylcysteinylglycine and N-D-lactoylcysteine by gamma-glutamyl transferase and dipeptidase (PMID: 8632674). S-lactoylglutathione has also been shown to modulate microtubule assembly (PMID: 690442). [HMDB]. S-Lactoylglutathione is found in many foods, some of which are blackcurrant, oat, pomegranate, and brussel sprouts.
S-Lactoylglutathione is a substrate of lactoylglutathione lyase [EC 4.4.1.5] in pyruvate metabolism (KEGG). Another enzyme, glyoxalase I, synthesizes this compound by converting methylglyoxal and reduced glutathione to S-lactoylglutathione. S-D-lactoylglutathione can be hydrolysed by thiolesterases to reduced glutathione and D-lactate but also converted to N-D-lactoylcysteinylglycine and N-D-lactoylcysteine by gamma-glutamyl transferase and dipeptidase (PMID: 8632674). S-lactoylglutathione has also been shown to modulate microtubule assembly (PMID: 690442).
Acquisition and generation of the data is financially supported in part by CREST/JST.
D000970 - Antineoplastic Agents
KEIO_ID L016; [MS3] KO009026
KEIO_ID L016; [MS2] KO009024
KEIO_ID L016

同义名列表

17 个代谢物同义名

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid; N-(N-L-gamma-Glutamyl-S-(2-hydroxy-1-oxopropyl)-L-cysteinyl)-glycine; S-[(2R)-2-Hydroxypropanoyl]-gamma-L-glutamyl-L-cysteinylglycine; S-delta-Lactoyl-glutathione; S-delta-Lactoylglutathione; delta-Lactoylglutathione; (R)-S-Lactoylglutathione; S-D-Lactoyl-glutathione; S-D-Lactoylglutathione; S-Lactoyl-glutathione; S-Lactate glutathione; S-Lactateglutathione; S-Lactoylglutathione; D-Lactoylglutathione; S-Lactylglutathione; NSC651836; S-Lactoylglutathione



数据库引用编号

41 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(3)

BioCyc(0)

PlantCyc(0)

代谢反应

103 个相关的代谢反应过程信息。

Reactome(72)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(29)

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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 AKR1B1, CASP3, GAPDH, GLO1, HAGH, KRIT1, PFDN5, PRKX, TLR2
Endosome membrane 1 LDLR
Endoplasmic reticulum membrane 2 CD59, PROS1
Nucleus 4 CASP3, GAPDH, PFDN5, PRKX
cytosol 7 AKR1B1, CASP3, GAPDH, GLO1, GSS, HAGH, PFDN5
nucleoplasm 4 AKR1B1, CASP3, GLO1, PRKX
Cell membrane 3 CD59, LDLR, TNF
Synapse 1 ACAN
cell surface 4 CD59, LDLR, TLR2, TNF
glutamatergic synapse 3 ACAN, CASP3, CPNE4
Golgi apparatus 2 LDLR, TLR2
Golgi membrane 3 CD59, INS, PROS1
mitochondrial inner membrane 1 LDHD
neuronal cell body 2 CASP3, TNF
Cytoplasm, cytosol 1 GAPDH
Lysosome 1 LDLR
plasma membrane 11 CD59, CPNE4, F2, GAPDH, GLO1, KRIT1, LDLR, PROS1, SIGLEC12, TLR2, TNF
Membrane 5 CD59, GAPDH, LDLR, SIGLEC12, TLR2
basolateral plasma membrane 1 LDLR
extracellular exosome 8 AKR1B1, CD59, CPNE4, F2, GAPDH, GLO1, GSS, PROS1
endoplasmic reticulum 1 PROS1
extracellular space 8 ACAN, AKR1B1, CD59, F2, INS, KRIT1, PROS1, TNF
lysosomal lumen 1 ACAN
perinuclear region of cytoplasm 1 GAPDH
mitochondrion 3 AKR1B1, HAGH, LDHD
protein-containing complex 1 KRIT1
intracellular membrane-bounded organelle 1 GAPDH
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 LDLR, TLR2
Secreted 3 F2, INS, PROS1
extracellular region 5 ACAN, F2, INS, PROS1, TNF
Single-pass membrane protein 2 LDLR, SIGLEC12
Mitochondrion matrix 1 HAGH
mitochondrial matrix 1 HAGH
nuclear membrane 1 GAPDH
external side of plasma membrane 3 CD59, LDLR, TNF
Secreted, extracellular space, extracellular matrix 1 ACAN
low-density lipoprotein particle 1 LDLR
microtubule cytoskeleton 1 GAPDH
Early endosome 1 LDLR
Membrane, clathrin-coated pit 1 LDLR
apical part of cell 1 LDLR
cell-cell junction 1 KRIT1
clathrin-coated pit 1 LDLR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 2 CD59, GAPDH
Cytoplasm, perinuclear region 1 GAPDH
Membrane raft 2 TLR2, TNF
Cytoplasm, cytoskeleton 1 GAPDH
focal adhesion 1 CD59
GABA-ergic synapse 1 ACAN
basement membrane 1 ACAN
collagen-containing extracellular matrix 2 ACAN, F2
Late endosome 1 LDLR
receptor complex 2 LDLR, TLR2
Cytoplasmic vesicle, phagosome membrane 1 TLR2
cell projection 1 TLR2
phagocytic cup 1 TNF
phagocytic vesicle membrane 1 TLR2
cytoskeleton 2 GAPDH, KRIT1
blood microparticle 2 F2, PROS1
Lipid-anchor, GPI-anchor 1 CD59
Endomembrane system 1 LDLR
endosome lumen 1 INS
sorting endosome 1 LDLR
Lipid droplet 1 GAPDH
specific granule membrane 1 CD59
tertiary granule membrane 1 CD59
cell body 1 TLR2
side of membrane 1 CD59
intermediate filament cytoskeleton 1 PFDN5
secretory granule lumen 1 INS
secretory granule membrane 1 TLR2
Golgi lumen 4 ACAN, F2, INS, PROS1
endoplasmic reticulum lumen 2 F2, INS
platelet alpha granule lumen 1 PROS1
transport vesicle 2 CD59, INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 CD59, INS
perineuronal net 1 ACAN
ER to Golgi transport vesicle membrane 1 CD59
[Isoform 2]: Cytoplasm 1 HAGH
clathrin-coated endocytic vesicle membrane 1 LDLR
ribonucleoprotein complex 1 GAPDH
prefoldin complex 1 PFDN5
endolysosome membrane 1 LDLR
death-inducing signaling complex 1 CASP3
somatodendritic compartment 1 LDLR
GAIT complex 1 GAPDH
Toll-like receptor 1-Toll-like receptor 2 protein complex 1 TLR2
Toll-like receptor 2-Toll-like receptor 6 protein complex 1 TLR2
PCSK9-LDLR complex 1 LDLR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
perisynaptic extracellular matrix 1 ACAN
[Isoform 1]: Mitochondrion matrix 1 HAGH
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Gerry Aplang Jana, Latifa Al Kharusi, Ramanjulu Sunkar, Rashid Al-Yahyai, Mahmoud W Yaish. Metabolomic analysis of date palm seedlings exposed to salinity and silicon treatments. Plant signaling & behavior. 2019; 14(11):1663112. doi: 10.1080/15592324.2019.1663112. [PMID: 31505987]
  • Ajit Ghosh, Ashwani Pareek, Sudhir K Sopory, Sneh L Singla-Pareek. A glutathione responsive rice glyoxalase II, OsGLYII-2, functions in salinity adaptation by maintaining better photosynthesis efficiency and anti-oxidant pool. The Plant journal : for cell and molecular biology. 2014 Oct; 80(1):93-105. doi: 10.1111/tpj.12621. [PMID: 25039836]
  • Ioannis S Minas, Georgia Tanou, Maya Belghazi, Dominique Job, George A Manganaris, Athanassios Molassiotis, Miltiadis Vasilakakis. Physiological and proteomic approaches to address the active role of ozone in kiwifruit post-harvest ripening. Journal of experimental botany. 2012 Apr; 63(7):2449-64. doi: 10.1093/jxb/err418. [PMID: 22268155]
  • Miklós Péter Kalapos. S-D-lactoylglutathione as a potential state marker for hemolysis. Medical hypotheses. 2011 Oct; 77(4):479-80. doi: 10.1016/j.mehy.2011.06.014. [PMID: 21723671]
  • Ananda Mustafiz, Khirod K Sahoo, Sneh L Singla-Pareek, Sudhir K Sopory. Metabolic engineering of glyoxalase pathway for enhancing stress tolerance in plants. Methods in molecular biology (Clifton, N.J.). 2010; 639(?):95-118. doi: 10.1007/978-1-60761-702-0_6. [PMID: 20387042]
  • Y Usui, M Nakase, H Hotta, A Urisu, N Aoki, K Kitajima, T Matsuda. A 33-kDa allergen from rice (Oryza sativa L. Japonica). cDNA cloning, expression, and identification as a novel glyoxalase I. The Journal of biological chemistry. 2001 Apr; 276(14):11376-81. doi: 10.1074/jbc.m010337200. [PMID: 11139585]
  • T Neuefeind, R Huber, H Dasenbrock, L Prade, B Bieseler. Crystal structure of herbicide-detoxifying maize glutathione S-transferase-I in complex with lactoylglutathione: evidence for an induced-fit mechanism. Journal of molecular biology. 1997 Dec; 274(4):446-53. doi: 10.1006/jmbi.1997.1402. [PMID: 9417926]
  • A C McLellan, S A Phillips, P J Thornalley. The assay of S-D-lactoylglutathione in biological systems. Biochemical Society transactions. 1993 May; 21(2):164S. doi: 10.1042/bst021164s. [PMID: 8359417]
  • L Edwards, J D Clelland, P J Thornalley. Characteristics of the inhibition of human promyelocytic leukaemia HL60 cell growth by S-D-lactoylglutathione in vitro. Leukemia research. 1993 Apr; 17(4):305-10. doi: 10.1016/0145-2126(93)90017-f. [PMID: 8487580]
  • M P Kalapos, T Garzó, F Antoni, J Mandl. Accumulation of S-D-lactoylglutathione and transient decrease of glutathione level caused by methylglyoxal load in isolated hepatocytes. Biochimica et biophysica acta. 1992 Jun; 1135(2):159-64. doi: 10.1016/0167-4889(92)90132-u. [PMID: 1616937]
  • P J Thornalley, V Della Bianca, P Bellavite, F Rossi. S-D-lactoylglutathione in resting and activated human neutrophils. Biochemical and biophysical research communications. 1987 Jun; 145(2):769-74. doi: 10.1016/0006-291x(87)91031-x. [PMID: 3593370]
  • I V Berezin, B M Kershengol'ts, N N Ugarova. [Microenvironment of enzymes as 1 of the factors determining enzyme stability. Stabilization of soluble and immobilized horseradish peroxidase]. Doklady Akademii nauk SSSR. 1975 Aug; 223(5):1256-9. doi: NULL. [PMID: 223]