S-methylcysteine (BioDeep_00000019380)

 

Secondary id: BioDeep_00000000759, BioDeep_00000227119, BioDeep_00000405512, BioDeep_00000418803, BioDeep_00000897493, BioDeep_00001872403

human metabolite PANOMIX_OTCML-2023 blood metabolite natural product


代谢物信息卡片


S-methylcysteine, hydrochloride, (L-Cys)-isomer

化学式: C4H9NO2S (135.0354)
中文名称: S-甲基-L-半胱氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 44.27%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

S-methylcysteine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/s-methylcysteine (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000019380). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CSCC(C(=O)O)N
InChI: InChI=1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1

描述信息

Methylcysteine is one of the identified number of bioactive substances in garlic that are water soluble (PMID 16484549). It has been suggested that the use of these organosulfur agents derived from garlic could protect partially oxidized and glycated LDL or plasma against further oxidative and glycative deterioration, which might benefit patients with diabetic-related vascular diseases (PMID 15161248). It may also exert some chemopreventive effects on chemical carcinogenesis. However, it should be borne in mind that may also demonstrate promotion potential, depending on the organ examined (PMID 9591199). Methylcystein is a biomarker for the consumption of dried and cooked beans.
S-n-methylcysteine, also known as (2r)-2-amino-3-(methylsulfanyl)propanoic acid or 3-(methylthio)-L-alanine, is a member of the class of compounds known as L-cysteine-s-conjugates. L-cysteine-s-conjugates are compounds containing L-cysteine where the thio-group is conjugated. S-n-methylcysteine is soluble (in water) and a moderately acidic compound (based on its pKa). S-n-methylcysteine can be found in soft-necked garlic, which makes S-n-methylcysteine a potential biomarker for the consumption of this food product. S-n-methylcysteine can be found primarily in blood and urine.
S-Methyl-L-cysteine is a natural product that acts as a substrate in the catalytic antioxidant system mediated by methionine sulfoxide reductase A (MSRA), with antioxidative, neuroprotective, and anti-obesity activities.

同义名列表

28 个代谢物同义名

S-methylcysteine, hydrochloride, (L-Cys)-isomer; (2R)-2-Amino-3-(methylsulphanyl)propanoic acid; (2S)-2-amino-3-(methylsulfanyl)propanoic acid; (2R)-2-amino-3-(methylsulfanyl)propanoic acid; (2R)-2-Amino-3-(methylsulphanyl)propanoate; (2R)-2-Amino-3-(methylsulfanyl)propanoate; (R)-2-amino-3-(methylthio)propanoic acid; (R)-2-Amino-3-(methylthio)propanoate; S-Acetamidomethyl-deamino-cysteine; S-methylcysteine, (DL-Cys)-isomer; S-methylcysteine, (L-Cys)-isomer; L-Aspartic acid dimethyl ester; 3-(Methylthio)-L-(8ci)alanine; S-Methyl-(9ci)-L-cysteine; 3-(methylthio)-L-alanine; S-11C-methyl-L-cysteine; Acm-thiopropionic acid; S-Methyl-DL-cysteine; S-Methyl-L-cysteine; L-S-methylcysteine; S-N-Methylcysteine; Acm-thiopropionate; S-Methyl cysteine; S-methyl-cysteine; S-methylcysteine; L-Methylcysteine; Methylcysteine; S-Methyl-L-cysteine



数据库引用编号

19 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

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)

24 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 AIMP2, ALB, BCL2, CASP8, CAT, HPGDS, MSRA, ODC1, PTGS2
Peripheral membrane protein 2 GORASP1, PTGS2
Endoplasmic reticulum membrane 2 BCL2, PTGS2
Nucleus 6 AIMP2, ALB, BCL2, CASP8, MPO, PCNA
cytosol 12 AIMP2, ALB, BCL2, CASP8, CAT, GPT, GSR, HPGDS, MSRA, NGF, ODC1, TDO2
dendrite 1 NGF
nuclear body 1 PCNA
centrosome 2 ALB, PCNA
nucleoplasm 5 CASP8, HPGDS, MPO, MSRA, PCNA
Cell membrane 1 TNF
Lipid-anchor 1 MSRA
Cytoplasmic side 1 GORASP1
lamellipodium 1 CASP8
Golgi apparatus membrane 1 GORASP1
cell surface 1 TNF
Golgi apparatus 2 ALB, GORASP1
Golgi membrane 2 GORASP1, INS
neuronal cell body 1 TNF
synaptic vesicle 1 NGF
Cytoplasm, cytosol 1 AIMP2
Lysosome 1 MPO
plasma membrane 2 MSRA, TNF
Membrane 4 AIMP2, BCL2, CAT, MSRA
axon 1 NGF
caveola 1 PTGS2
extracellular exosome 7 ALB, CAT, GPT, GSR, MPO, MSRA, PCNA
endoplasmic reticulum 3 ALB, BCL2, PTGS2
extracellular space 7 ALB, IL10, IL6, INS, MPO, NGF, TNF
mitochondrion 5 BCL2, CASP8, CAT, GSR, MSRA
protein-containing complex 5 ALB, BCL2, CASP8, CAT, PTGS2
intracellular membrane-bounded organelle 4 CAT, HPGDS, MPO, MSRA
Microsome membrane 1 PTGS2
Secreted 5 ALB, IL10, IL6, INS, NGF
extracellular region 8 ALB, CAT, IL10, IL6, INS, MPO, NGF, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, CASP8
mitochondrial matrix 2 CAT, GSR
anchoring junction 1 ALB
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 GSR, TNF
actin cytoskeleton 1 MSRA
midbody 1 MSRA
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cell projection, lamellipodium 1 CASP8
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 1 CAT
cis-Golgi network 1 GORASP1
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
secretory granule 1 MPO
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
ciliary basal body 1 ALB
chromatin 1 PCNA
phagocytic cup 1 TNF
cytoskeleton 1 CASP8
centriole 1 ALB
spindle pole 1 ALB
nuclear replication fork 1 PCNA
chromosome, telomeric region 1 PCNA
blood microparticle 1 ALB
endosome lumen 2 INS, NGF
cell body 1 CASP8
replication fork 1 PCNA
myelin sheath 1 BCL2
azurophil granule 1 MPO
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 2 INS, NGF
endoplasmic reticulum lumen 4 ALB, IL6, INS, PTGS2
male germ cell nucleus 1 PCNA
platelet alpha granule lumen 1 ALB
transport vesicle 1 INS
azurophil granule lumen 1 MPO
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GORASP1, INS
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
nuclear lamina 1 PCNA
phagocytic vesicle lumen 1 MPO
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 1 CASP8
ripoptosome 1 CASP8
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
cyclin-dependent protein kinase holoenzyme complex 1 PCNA
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
BAD-BCL-2 complex 1 BCL2
PCNA complex 1 PCNA
PCNA-p21 complex 1 PCNA
replisome 1 PCNA
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


文献列表

  • Fangxu Guan, Wenwen Du, Jiguo Zhang, Chang Su, Bing Zhang, Kui Deng, Shufa Du, Huijun Wang. Amino Acids and Lipids Associated with Long-Term and Short-Term Red Meat Consumption in the Chinese Population: An Untargeted Metabolomics Study. Nutrients. 2021 Dec; 13(12):. doi: 10.3390/nu13124567. [PMID: 34960119]
  • Hyo Kyozuka, Toma Fukuda, Tsuyoshi Murata, Yuta Endo, Aya Kanno, Shun Yasuda, Akiko Yamaguchi, Miho Ono, Akiko Sato, Koichi Hashimoto, Keiya Fujimori. Comprehensive metabolomic analysis of first-trimester serum identifies biomarkers of early-onset hypertensive disorder of pregnancy. Scientific reports. 2020 08; 10(1):13857. doi: 10.1038/s41598-020-70974-3. [PMID: 32807817]
  • Jaya Joshi, Justin B Renaud, Mark W Sumarah, Frédéric Marsolais. Deciphering S-methylcysteine biosynthesis in common bean by isotopic tracking with mass spectrometry. The Plant journal : for cell and molecular biology. 2019 10; 100(1):176-186. doi: 10.1111/tpj.14438. [PMID: 31215701]
  • Mohammed A El-Magd, Walied S Abdo, Mustafa El-Maddaway, Nasr M Nasr, Rasha A Gaber, Eman S El-Shetry, Ayman A Saleh, Faisal Abdulrahman Ali Alzahrani, Doaa H Abdelhady. High doses of S-methylcysteine cause hypoxia-induced cardiomyocyte apoptosis accompanied by engulfment of mitochondaria by nucleus. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Oct; 94(?):589-597. doi: 10.1016/j.biopha.2017.07.100. [PMID: 28783581]
  • De-Cheng Tsai, Meng-Chieh Liu, Yi-Reng Lin, Mei-Fang Huang, Shih-Shin Liang. A novel reductive amination method with isotopic formaldehydes for the preparation of internal standard and standards for determining organosulfur compounds in garlic. Food chemistry. 2016 Apr; 197(Pt A):692-8. doi: 10.1016/j.foodchem.2015.11.022. [PMID: 26617005]
  • Dengqun Liao, Agnieszka Pajak, Steven R Karcz, B Patrick Chapman, Andrew G Sharpe, Ryan S Austin, Raju Datla, Sangeeta Dhaubhadel, Frédéric Marsolais. Transcripts of sulphur metabolic genes are co-ordinately regulated in developing seeds of common bean lacking phaseolin and major lectins. Journal of experimental botany. 2012 Oct; 63(17):6283-95. doi: 10.1093/jxb/ers280. [PMID: 23066144]
  • Ernest K Lee, Angelica Cibrian-Jaramillo, Sergios-Orestis Kolokotronis, Manpreet S Katari, Alexandros Stamatakis, Michael Ott, Joanna C Chiu, Damon P Little, Dennis Wm Stevenson, W Richard McCombie, Robert A Martienssen, Gloria Coruzzi, Rob Desalle. A functional phylogenomic view of the seed plants. PLoS genetics. 2011 Dec; 7(12):e1002411. doi: 10.1371/journal.pgen.1002411. [PMID: 22194700]
  • Fuqiang Yin, Agnieszka Pajak, Ralph Chapman, Andrew Sharpe, Shangzhi Huang, Frédéric Marsolais. Analysis of common bean expressed sequence tags identifies sulfur metabolic pathways active in seed and sulfur-rich proteins highly expressed in the absence of phaseolin and major lectins. BMC genomics. 2011 May; 12(?):268. doi: 10.1186/1471-2164-12-268. [PMID: 21615926]
  • Federico M Rubino, Marco Pitton, Daniela Di Fabio, Giuseppe Meroni, Enzo Santaniello, Enrico Caneva, Marco Pappini, Antonio Colombi. Measurement of S-methylcysteine and S-methyl-mercapturic acid in human urine by alkyl-chloroformate extractive derivatization and isotope-dilution gas chromatography-mass spectrometry. Biomedical chromatography : BMC. 2011 Mar; 25(3):330-43. doi: 10.1002/bmc.1451. [PMID: 21110385]
  • Monika Janczarek, Jolanta Kutkowska, Tomasz Piersiak, Anna Skorupska. Rhizobium leguminosarum bv. trifolii rosR is required for interaction with clover, biofilm formation and adaptation to the environment. BMC microbiology. 2010 Nov; 10(?):284. doi: 10.1186/1471-2180-10-284. [PMID: 21070666]
  • Lisa A Brennan, Wanda Lee, Marc Kantorow. TXNL6 is a novel oxidative stress-induced reducing system for methionine sulfoxide reductase a repair of α-crystallin and cytochrome C in the eye lens. PloS one. 2010 Nov; 5(11):e15421. doi: 10.1371/journal.pone.0015421. [PMID: 21079812]
  • Matthew W Himmelstein, Thomas A Kegelman, Michael P DeLorme, Nancy E Everds, John C O'Connor, Raymond A Kemper, Diane L Nabb, Beth E Mileson, Christopher Bevan. Two-day inhalation toxicity study of methyl iodide in the rat. Inhalation toxicology. 2009 May; 21(6):480-7. doi: 10.1080/08958370802596892. [PMID: 19519148]
  • E Sloter, M Nemec, D Stump, J Holson, D Kirkpatrick, M Gargas, J Kinzell. Methyl iodide-induced fetal hypothyroidism implicated in late-stage fetal death in rabbits. Inhalation toxicology. 2009 May; 21(6):462-79. doi: 10.1080/08958370802596942. [PMID: 19519147]
  • Michael P DeLorme, Mathew W Himmelstein, Raymond A Kemper, Thomas A Kegelman, Michael L Gargas, John H Kinzell. Evaluation of respiratory parameters in rats and rabbits exposed to methyl iodide. Inhalation toxicology. 2009 May; 21(6):505-11. doi: 10.1080/08958370802596926. [PMID: 19519150]
  • M E Schranz, A J Manzaneda, A J Windsor, M J Clauss, T Mitchell-Olds. Ecological genomics of Boechera stricta: identification of a QTL controlling the allocation of methionine- vs branched-chain amino acid-derived glucosinolates and levels of insect herbivory. Heredity. 2009 May; 102(5):465-74. doi: 10.1038/hdy.2009.12. [PMID: 19240753]
  • Hadar Less, Gad Galili. Coordinations between gene modules control the operation of plant amino acid metabolic networks. BMC systems biology. 2009 Jan; 3(?):14. doi: 10.1186/1752-0509-3-14. [PMID: 19171064]
  • Hazem A H Kataya, Alaaeldin A Hamza. Red Cabbage (Brassica oleracea) Ameliorates Diabetic Nephropathy in Rats. Evidence-based complementary and alternative medicine : eCAM. 2008 Sep; 5(3):281-7. doi: 10.1093/ecam/nem029. [PMID: 18830445]
  • Meghan Taylor, Ralph Chapman, Ronald Beyaert, Cinta Hernández-Sebastià, Frédéric Marsolais. Seed storage protein deficiency improves sulfur amino acid content in common bean (Phaseolus vulgaris L.): redirection of sulfur from gamma-glutamyl-S-methyl-cysteine. Journal of agricultural and food chemistry. 2008 Jul; 56(14):5647-54. doi: 10.1021/jf800787y. [PMID: 18588315]
  • Sheng-lei Yan, Mei-chin Yin. Protective and alleviative effects from 4 cysteine-containing compounds on ethanol-induced acute liver injury through suppression of oxidation and inflammation. Journal of food science. 2007 Sep; 72(7):S511-5. doi: 10.1111/j.1750-3841.2007.00449.x. [PMID: 17995665]
  • Chiu-mei Chen, Mei-chin Yin, Cheng-chin Hsu, Ting-chun Liu. Antioxidative and anti-inflammatory effects of four cysteine-containing agents in striatum of MPTP-treated mice. Nutrition (Burbank, Los Angeles County, Calif.). 2007 Jul; 23(7-8):589-97. doi: 10.1016/j.nut.2007.05.004. [PMID: 17574387]
  • Mei-chin Yin, Cheng-chin Hsu, Pei-fang Chiang, Wen-jean Wu. Antiinflammatory and antifibrogenic effects of s-ethyl cysteine and s-methyl cysteine in the kidney of diabetic mice. Molecular nutrition & food research. 2007 May; 51(5):572-9. doi: 10.1002/mnfr.200600213. [PMID: 17440992]
  • Chun-che Lin, Mei-chin Yin, Cheng-chin Hsu, Meng-pei Lin. Effect of five cysteine-containing compounds on three lipogenic enzymes in Balb/cA mice consuming a high saturated fat diet. Lipids. 2004 Sep; 39(9):843-8. doi: 10.1007/s11745-004-1305-4. [PMID: 15669759]
  • José Pedraza-Chaverrí, Mariana Gil-Ortiz, Gabriela Albarrán, Laura Barbachano-Esparza, Marta Menjívar, Omar N Medina-Campos. Garlic's ability to prevent in vitro Cu2+-induced lipoprotein oxidation in human serum is preserved in heated garlic: effect unrelated to Cu2+-chelation. Nutrition journal. 2004 Sep; 3(?):10. doi: 10.1186/1475-2891-3-10. [PMID: 15341661]
  • Chien-Ning Huang, Joeu-Shyan Horng, Mei-Chin Yin. Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma. Journal of agricultural and food chemistry. 2004 Jun; 52(11):3674-8. doi: 10.1021/jf0307292. [PMID: 15161248]
  • Danielle R Ellis, Thomas G Sors, Dennis G Brunk, Carrie Albrecht, Cindy Orser, Brett Lahner, Karl V Wood, Hugh H Harris, Ingrid J Pickering, David E Salt. Production of Se-methylselenocysteine in transgenic plants expressing selenocysteine methyltransferase. BMC plant biology. 2004 Jan; 4(?):1. doi: 10.1186/1471-2229-4-1. [PMID: 15005814]
  • Cheng-chin Hsu, Chien-ning Huang, Yu-chuan Hung, Mei-chin Yin. Five cysteine-containing compounds have antioxidative activity in Balb/cA mice. The Journal of nutrition. 2004 Jan; 134(1):149-52. doi: 10.1093/jn/134.1.149. [PMID: 14704308]
  • Ohki Higuchi, Koutaro Tateshita, Hiroyuki Nishimura. Antioxidative activity of sulfur-containing compounds in Allium species for human low-density lipoprotein (LDL) oxidation in vitro. Journal of agricultural and food chemistry. 2003 Nov; 51(24):7208-14. doi: 10.1021/jf034294u. [PMID: 14611195]
  • A L Buchwald, M Müller. Late confirmation of acute methyl bromide poisoning using S-methylcysteine adduct testing. Veterinary and human toxicology. 2001 Aug; 43(4):208-11. doi: . [PMID: 11474733]
  • H W Goergens, E Hallier, A Müller, H M Bolt. Macromolecular adducts in the use of methyl bromide as fumigant. Toxicology letters. 1994 Jun; 72(1-3):199-203. doi: 10.1016/0378-4274(94)90029-9. [PMID: 8202932]
  • E F Karim, J S Millership, D J Temple, A D Woolfson. An investigation of the metabolism of S-carboxymethyl-L-cysteine in man using a novel HPLC-ECD method. European journal of drug metabolism and pharmacokinetics. 1988 Oct; 13(4):253-6. doi: 10.1007/bf03190087. [PMID: 3243319]
  • P B Farmer, E G Shuker, I Bird. DNA and protein adducts as indicators of in vivo methylation by nitrosatable drugs. Carcinogenesis. 1986 Jan; 7(1):49-52. doi: 10.1093/carcin/7.1.49. [PMID: 3943144]
  • R J Nolan, D L Rick, T D Landry, L P McCarty, G L Agin, J H Saunders. Pharmacokinetics of inhaled methyl chloride (CH3Cl) in male volunteers. Fundamental and applied toxicology : official journal of the Society of Toxicology. 1985 Apr; 5(2):361-9. doi: 10.1016/0272-0590(85)90084-3. [PMID: 3988005]
  • S C Mitchell, R L Smith, R H Waring, G F Aldington. The metabolism of S-methyl-L-cysteine in man. Xenobiotica; the fate of foreign compounds in biological systems. 1984 Oct; 14(10):767-79. doi: 10.3109/00498258409151475. [PMID: 6506751]
  • M D Eyre, D E Phillips, I M Evans, A Thompson. The nutritional role of S-Methyl-L-cysteine. Journal of the science of food and agriculture. 1983 Jul; 34(7):696-700. doi: 10.1002/jsfa.2740340705. [PMID: 6620984]
  • R van Doorn, P J Borm, C M Leijdekkers, P T Henderson, J Reuvers, T J van Bergen. Detection and identification of S-methylcysteine in urine of workers exposed to methyl chloride. International archives of occupational and environmental health. 1980; 46(2):99-109. doi: 10.1007/bf00378189. [PMID: 7399728]
  • M D Armstrong. N-delta-acetylornithine and S-methylcysteine in blood plasma. Biochimica et biophysica acta. 1979 Nov; 587(4):638-42. doi: 10.1016/0304-4165(79)90015-1. [PMID: 508804]
  • E A BARNSLEY, L YOUNG. BIOCHEMICAL STUDIES OF TOXIC AGENTS. THE METABOLISM OF IODOMETHANE. The Biochemical journal. 1965 Apr; 95(?):77-81. doi: 10.1042/bj0950077. [PMID: 14333570]
  • V M CRADDOCK. REACTION OF THE CARCINOGEN DIMETHYLNITROSAMINE WITH PROTEINS AND WITH THIOL COMPOUNDS IN THE INTACT ANIMAL. The Biochemical journal. 1965 Feb; 94(?):323-30. doi: 10.1042/bj0940323. [PMID: 14348192]
  • F TOMINAGA, S KOBAYASHI, I MUTA, H TAKEI, M ICHINOSE. ON THE ISOLATION AND IDENTIFICATION OF S-METHYLCYSTEINE FROM HUMAN URINE. Journal of biochemistry. 1963 Sep; 54(?):220-4. doi: 10.1093/oxfordjournals.jbchem.a127775. [PMID: 14070449]
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