Dimethyl sulphone (BioDeep_00000008513)

Secondary id: BioDeep_00000405596, BioDeep_00000866166

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 Volatile Flavor Compounds

代谢物信息卡片

Methane, 1,1′-sulfonylbis-

化学式: C2H6O2S (94.0088496)
中文名称: 二甲基砜
谱图信息: 最多检出来源 Homo sapiens(blood) 0.21%

Reviewed

Last reviewed on 2024-08-21.

Cite this Page

Dimethyl sulphone. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/dimethyl_sulphone (retrieved 2024-11-24) (BioDeep RN: BioDeep_00000008513). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CS(=O)(=O)C
InChI: InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3

描述信息

Dimethyl sulfone, also known as sulfonylbismethane or lignisul MSM, belongs to the class of organic compounds known as sulfones. Sulfones are compounds containing a sulfonyl group, which has the general structure RS(=O)2R (R,R =alkyl, aryl), attached to two carbon atoms. Dimethyl sulfone (DMSO2) is an organic sulfur compound belonging to a class of chemicals known as sulfones. It derives from dietary sources, from intestinal bacterial metabolism and from human endogenous methanethiol metabolism. DMSO2 reflects its close chemical relationship to dimethyl sulfoxide (DMSO), which differs only in the oxidation state of the sulfur atom. Dimethyl sulfone is possibly neutral. Dimethyl sulfone exists in all living organisms, ranging from bacteria to humans. DMSO2 is the primary metabolite of DMSO in humans, and it shares some of the properties of DMSO. Dimethyl sulfone is sulfurous tasting compound. dimethyl sulfone is found on average in the highest concentration in milk (cow). Dimethyl sulfone has also been detected, but not quantified in asparagus and guava. This could make dimethyl sulfone a potential biomarker for the consumption of these foods. Dimethyl sulfone can be found in Afipia. It occurs naturally in some primitive plants and is present in small amounts in many foods and beverages. Dimethyl sulfone can be found in plasma and CSF of normal humans.
Methylsulfonylmethane (MSM) is an organosulfur compound with the formula (CH3)2SO2. It is also known by several other names including DMSO2, methyl sulfone, and dimethyl sulfone. This colorless solid features the sulfonyl functional group and is considered relatively inert chemically. It occurs naturally in some primitive plants and is present in small amounts in many foods and beverages and it is marketed as a dietary supplement. Dimethyl sulfone is found in guava.
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2198 - Nonnarcotic Analgesic
D000893 - Anti-Inflammatory Agents
Dimethyl sulfone (Methyl Sulfonyl Methane) is a metabolic product of endogenous methanethiol metabolism and intestinal bacterial metabolism. Dimethyl sulfone inhibits choriocapillary endothelial (CCE) cell proliferation, also has many biological effects, including antiinflammatory, antioxidant, and local anesthetic effects that could be neuroprotective[1][2][3].
Dimethyl sulfone (Methyl Sulfonyl Methane) is a metabolic product of endogenous methanethiol metabolism and intestinal bacterial metabolism. Dimethyl sulfone inhibits choriocapillary endothelial (CCE) cell proliferation, also has many biological effects, including antiinflammatory, antioxidant, and local anesthetic effects that could be neuroprotective[1][2][3].

同义名列表

18 个代谢物同义名

Dimethyl sulfone, 13C-labeled; (Methylsulfonyl)methane; methanesulfonylmethane; Methylsulphonylmethane; Methylsulfonylmethane; Methyl sulfonmethane; Sulphonylbismethane; Sulfonylbis-methane; Sulfonylbismethane; Sulphonyldimethane; Dimethyl sulphone; Dimethyl sulfone; Dimethylsulfone; Methyl sulfone; Lignisul MSM; Opti MSM; Dimethyl sulfone; Dimethyl sulfone

数据库引用编号

18 个数据库交叉引用编号

ChEBI: CHEBI:9349
KEGG: C11142
PubChem: 6213
HMDB: HMDB0004983
Metlin: METLIN7236
DrugBank: DB14090
ChEMBL: CHEMBL25028
Wikipedia: Methylsulfonylmethane
foodb: FDB006725
chemspider: 5978
CAS: 67-71-0
PMhub: MS000022138
NIKKAJI: J1.412E
RefMet: Dimethyl sulfone
medchemexpress: HY-Y1314
BioNovoGene_Lab2019: BioNovoGene_Lab2019-833
PubChem: 13324
KNApSAcK: 9349

分类词条

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

dimethyl sulfide degradation II (oxidation): H⁺ + NADPH + O₂ + dimethyl sulfide ⟶ H₂O + NADP⁺ + dimethyl sulfoxide
dimethyl sulfone degradation: H₂O + NAD⁺ + dimethyl sulfoxide ⟶ H⁺ + NADH + dimethyl sulfone
superpathway of dimethylsulfone degradation: H⁺ + NADH + O₂ + dimethyl sulfide ⟶ H₂O + NAD⁺ + formaldehyde + methanethiol

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

7 个相关的物种来源信息

1080010 - Aloe africana: 10.1021/JF010179C
3589 - Basella alba: 10.1016/0889-1575(91)90017-Z
3258 - Equisetum arvense: 10.1002/HLCA.19490320724
3262 - Equisetum hyemale L.: -
9606 - Homo sapiens: -
9606 - Homo sapiens: 10.1007/S11306-015-0840-5
120290 - Psidium guajava: 10.1080/10412905.1994.9698430

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

Elizabeth A Tanner, Melody A Gary, Stephan Michalik, Asheal A Davis, Brian K McFarlin. Optimized Curcumin, Pomegranate Extract, and Methylsulfonylmethane Reduce Acute, Systemic Inflammatory Response to a Half-marathon Race. Alternative therapies in health and medicine. 2022 Sep; 28(6):72-81. doi: . [PMID: 32619204]
Cameron V Fili, Ling Lin, Jonathan Chapman, David Hamilton, Charles R Yates. Methylsulfonylmethane and Sesame Seed Oil Improve Dyslipidemia and Modulate Polyunsaturated Fatty Acid Metabolism in Two Mouse Models of Diabetes. Journal of medicinal food. 2022 Jun; 25(6):607-617. doi: 10.1089/jmf.2021.0196. [PMID: 35708633]
Yueming Guo, Pengpeng Li, Zongliang Wang, Peibiao Zhang, Xiaodong Wu. Sustained Delivery of Methylsulfonylmethane from Biodegradable Scaffolds Enhances Efficient Bone Regeneration. International journal of nanomedicine. 2022; 17(?):4829-4842. doi: 10.2147/ijn.s377036. [PMID: 36246935]
Da-Yeon Lee, Chan-Yang Lee, Jin-Na Shin, Jeong-Ho Oh, Soon-Mi Shim. Impact of soy lecithin, zinc oxide, and methylsulfonylmethane, as excipient ingredients, on the bioaccessibility and intestinal transport of branched-chain amino acids from animal and plant protein mixtures. Food & function. 2021 Nov; 12(22):11399-11407. doi: 10.1039/d1fo01712h. [PMID: 34673869]
X Liu, S Robbins, J Eyles, T Fedorova, S Virk, L A Deveza, A J McLachlan, D J Hunter. Efficacy and safety of a supplement combination on hand pain among people with symptomatic hand osteoarthritis an internet-based, randomised clinical trial the RADIANT study. Osteoarthritis and cartilage. 2021 05; 29(5):667-677. doi: 10.1016/j.joca.2021.01.011. [PMID: 33617972]
M S Abdul Rasheed, U P Tiwari, J C Jespersen, L L Bauer, R N Dilger. Effects of methylsulfonylmethane and neutralizing anti-IL-10 antibody supplementation during a mild Eimeria challenge infection in broiler chickens. Poultry science. 2020 Dec; 99(12):6559-6568. doi: 10.1016/j.psj.2020.09.046. [PMID: 33248571]
Xiaoqian Liu, Sarah Robbins, Jillian Eyles, Tatyana Fedorova, Sonika Virk, Leticia A Deveza, Andrew McLachlan, David Hunter. Efficacy and safety of a supplement combination for hand osteoarthritis pain: protocol for an internet-based randomised placebo-controlled trial (The RADIANT study). BMJ open. 2020 02; 10(2):e035672. doi: 10.1136/bmjopen-2019-035672. [PMID: 32075845]
M S Abdul Rasheed, M L Oelschlager, B N Smith, L L Bauer, R A Whelan, R N Dilger. Dietary methylsulfonylmethane supplementation and oxidative stress in broiler chickens. Poultry science. 2020 Feb; 99(2):914-925. doi: 10.1016/j.psj.2019.12.010. [PMID: 32029168]
H L Yan, S C Cao, Y D Hu, H F Zhang, J B Liu. Effects of methylsulfonylmethane on growth performance, immunity, antioxidant capacity, and meat quality in Pekin ducks. Poultry science. 2020 Feb; 99(2):1069-1074. doi: 10.1016/j.psj.2019.10.002. [PMID: 32029143]
Xiaoqian Liu, David J Hunter, Jillian Eyles, Andrew J McLachlan, Jeffry Adiwidjaja, Shane K Eagles, XiaoSuo Wang. Pharmacokinetic assessment of constituents of Boswellia serrata, pine bark extracts, curcumin in combination including methylsulfonylmethane in healthy volunteers. The Journal of pharmacy and pharmacology. 2020 Jan; 72(1):121-131. doi: 10.1111/jphp.13184. [PMID: 31608447]
M S Abdul Rasheed, M L Oelschlager, B N Smith, L L Bauer, R A Whelan, R N Dilger. Toxicity and tissue distribution of methylsulfonylmethane following oral gavage in broilers. Poultry science. 2019 Oct; 98(10):4972-4981. doi: 10.3382/ps/pez265. [PMID: 31111938]
Paul Crawford, Amanda Crawford, Frederick Nielson, Robert Lystrup. Methylsulfonylmethane for treatment of low back pain: A safety analysis of a randomized, controlled trial. Complementary therapies in medicine. 2019 Aug; 45(?):85-88. doi: 10.1016/j.ctim.2019.05.022. [PMID: 31331587]
S Cheleschi, A Fioravanti, A De Palma, C Corallo, D Franci, N Volpi, G Bedogni, S Giannotti, N Giordano. Methylsulfonylmethane and mobilee prevent negative effect of IL-1β in human chondrocyte cultures via NF-κB signaling pathway. International immunopharmacology. 2018 Dec; 65(?):129-139. doi: 10.1016/j.intimp.2018.10.004. [PMID: 30316071]
Yves Henrotin, Ali Mobasheri. Natural Products for Promoting Joint Health and Managing Osteoarthritis. Current rheumatology reports. 2018 09; 20(11):72. doi: 10.1007/s11926-018-0782-9. [PMID: 30232562]
Ranjith Kumar Velusamy, Ramasamy Tamizhselvi. Protective effect of methylsulfonylmethane in caerulein-induced acute pancreatitis and associated lung injury in mice. The Journal of pharmacy and pharmacology. 2018 Sep; 70(9):1188-1199. doi: 10.1111/jphp.12946. [PMID: 29971769]
Francisco Adelvane de Paulo Rodrigues, Alan Diego da Conceição Santos, Pedro Henrique Quintela Soares de Medeiros, Mara de Moura Gondim Prata, Tailane Caína de Souza Santos, James Almada da Silva, Gerly Anne de Castro Brito, Armênio Aguiar Dos Santos, Edilberto Rocha Silveira, Aldo Ângelo Moreira Lima, Alexandre Havt. Gingerol suppresses sepsis-induced acute kidney injury by modulating methylsulfonylmethane and dimethylamine production. Scientific reports. 2018 08; 8(1):12154. doi: 10.1038/s41598-018-30522-6. [PMID: 30108263]
Thomas Wong, Richard J Bloomer, Rodney L Benjamin, Randal K Buddington. Small Intestinal Absorption of Methylsulfonylmethane (MSM) and Accumulation of the Sulfur Moiety in Selected Tissues of Mice. Nutrients. 2017 Dec; 10(1):. doi: 10.3390/nu10010019. [PMID: 29295596]
Y Jiao, J H Park, Y M Kim, I H Kim. Effects of dietary methyl sulfonyl methane (MSM) supplementation on growth performance, nutrient digestibility, meat quality, excreta microbiota, excreta gas emission, and blood profiles in broilers. Poultry science. 2017 Jul; 96(7):2168-2175. doi: 10.3382/ps/pew480. [PMID: 28339708]
Tommaso Cai, Daniele Tiscione, Luca Gallelli, Paolo Verze, Alessandro Palmieri, Vincenzo Mirone, Riccardo Bartoletti, Gianni Malossini. Serenoa repens associated with selenium and lycopene extract and bromelain and methylsulfonylmethane extract are able to improve the efficacy of levofloxacin in chronic bacterial prostatitis patients. Archivio italiano di urologia, andrologia : organo ufficiale [di] Societa italiana di ecografia urologica e nefrologica. 2016 Oct; 88(3):177-182. doi: 10.4081/aiua.2016.3.177. [PMID: 27711089]
Inês Sousa-Lima, Shin-Young Park, Michelle Chung, Hyun Ju Jung, Min-Cheol Kang, Joana M Gaspar, Ji A Seo, M Paula Macedo, Kyong Soo Park, Christos Mantzoros, Seung-Hoon Lee, Young-Bum Kim. Methylsulfonylmethane (MSM), an organosulfur compound, is effective against obesity-induced metabolic disorders in mice. Metabolism: clinical and experimental. 2016 10; 65(10):1508-21. doi: 10.1016/j.metabol.2016.07.007. [PMID: 27621186]
Cheng Z Wang, Amina El Ayadi, Juhi Goswamy, Celeste C Finnerty, Randy Mifflin, Linda Sousse, Perenlei Enkhbaatar, John Papaconstantinou, David N Herndon, Naseem H Ansari. Topically applied metal chelator reduces thermal injury progression in a rat model of brass comb burn. Burns : journal of the International Society for Burn Injuries. 2015 Dec; 41(8):1775-1787. doi: 10.1016/j.burns.2015.08.012. [PMID: 26392023]
G Merolla, F Dellabiancia, A Ingardia, P Paladini, G Porcellini. Co-analgesic therapy for arthroscopic supraspinatus tendon repair pain using a dietary supplement containing Boswellia serrata and Curcuma longa: a prospective randomized placebo-controlled study. Musculoskeletal surgery. 2015 Sep; 99 Suppl 1(?):S43-52. doi: 10.1007/s12306-015-0364-1. [PMID: 25957549]
Yilmaz Ucuncu, Nuray Celik, Cengiz Ozturk, Murat Turkoglu, Nihal Cetin, Nizamettin Kockara, Ebru Sener, Cihat Dundar, Aynur Arslan, Hasan Dogan, Nezahat Kurt, Halis Suleyman. Chondroprotective effects of a new glucosamine combination in rats: Gene expression, biochemical and histopathological evaluation. Life sciences. 2015 Jun; 130(?):31-7. doi: 10.1016/j.lfs.2015.03.012. [PMID: 25818190]
Ajoy Basak, Mukunda Goswami, Abishankari Rajkumar, Tapobrata Mitra, Swapan Majumdar, Paul O'Reilly, Hussam M Bdour, Vance L Trudeau, Amit Basak. Enediynyl peptides and iso-coumarinyl methyl sulfones as inhibitors of proprotein convertases PCSK8/SKI-1/S1P and PCSK4/PC4: Design, synthesis and biological evaluations. Bioorganic & medicinal chemistry letters. 2015; 25(10):2225-37. doi: 10.1016/j.bmcl.2015.03.029. [PMID: 25881830]
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Keyvan Amirshahrokhi, Shahab Bohlooli. Effect of methylsulfonylmethane on paraquat-induced acute lung and liver injury in mice. Inflammation. 2013 Oct; 36(5):1111-21. doi: 10.1007/s10753-013-9645-8. [PMID: 23595869]
Rehab Kamel, Engy M El Morsy. Hepatoprotective effect of methylsulfonylmethane against carbon tetrachloride-induced acute liver injury in rats. Archives of pharmacal research. 2013 Sep; 36(9):1140-8. doi: 10.1007/s12272-013-0110-x. [PMID: 23591777]
Nadia Ms Arafa, Hayam M Hamuda, Samuel T Melek, Sahar K Darwish. The effectiveness of Echinacea extract or composite glucosamine, chondroitin and methyl sulfonyl methane supplements on acute and chronic rheumatoid arthritis rat model. Toxicology and industrial health. 2013 Mar; 29(2):187-201. doi: 10.1177/0748233711428643. [PMID: 22173958]
Pawel Mochalski, Karin Krapf, Clemens Ager, Helmut Wiesenhofer, Agapios Agapiou, Milt Statheropoulos, Dietmar Fuchs, Ernst Ellmerer, Boguslaw Buszewski, Anton Amann. Temporal profiling of human urine VOCs and its potential role under the ruins of collapsed buildings. Toxicology mechanisms and methods. 2012 Sep; 22(7):502-11. doi: 10.3109/15376516.2012.682664. [PMID: 22482743]
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