Dimethylpropiothetin (BioDeep_00000005379)
Secondary id: BioDeep_00001869168
human metabolite blood metabolite Marine Natural Products
代谢物信息卡片
Sulfonium, (2-carboxyethyl)dimethyl-, chloride (1:1)
化学式: C5H10O2S (134.0401)
中文名称: 硫代甜菜碱
谱图信息:
最多检出来源 Homo sapiens(blood) 23.79%
分子结构信息
SMILES: C(=O)([O-])CC[S+](C)C
InChI: InChI=1S/C5H10O2S/c1-8(2)4-3-5(6)7/h3-4H2,1-2H3
描述信息
Dimethylsulfoniopropionate, also known as dimethylpropiothetin or S-dimethylsulfonium propionic acid, is a member of the class of compounds known as carboxylic acid salts. Carboxylic acid salts are ionic derivatives of carboxylic acid. Dimethylsulfoniopropionate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Dimethylsulfoniopropionate can be found in a number of food items such as sugar apple, american butterfish, coriander, and oxheart cabbage, which makes dimethylsulfoniopropionate a potential biomarker for the consumption of these food products. Dimethylsulfoniopropionate (DMSP), is an organosulfur compound with the formula (CH3)2S+CH2CH2COO−. This zwitterionic metabolite can be found in marine phytoplankton, seaweeds, and some species of terrestrial and aquatic vascular plants. It functions as an osmolyte as well as several other physiological and environmental roles have also been identified. DMSP was first identified in the marine red alga Polysiphonia fastigiata by Frederick Challenger and Margaret Simpson (later Dr. Whitaker) .
D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents
同义名列表
41 个代谢物同义名
Sulfonium, (2-carboxyethyl)dimethyl-, chloride (1:1); (2-Carboxyethyl)dimethylsulfonium chloride; beta-Dimethylsulphoniopropionic acid; Dimethyl-beta-propiothetin chloride; S-Dimethylsulphonium propionic acid; beta-Dimethylsulfoniopropionic acid; Dimethylsulfoniopropionate chloride; Dimethylpropiothetin hydrochloride; S-dimethylsulfonium propionic acid; 3-Dimethylsulphoniopropionic acid; b-Dimethylsulphoniopropionic acid; 3-(dimethylsulfaniumyl)propanoate; Β-dimethylsulphoniopropionic acid; 3-Dimethylsulfoniopropionic acid; beta-Dimethylsulphoniopropionate; b-Dimethylsulfoniopropionic acid; Β-dimethylsulfoniopropionic acid; beta-Dimethylsulfoniopropionate; Dimethylsulphoniopropionic acid; S-Dimethylsulphonium propionate; Dimethylsulfoniopropionic acid; S-Dimethylsulfonium propionate; S,S-Dimethyl-beta-propiothetin; 3-Dimethylsulphoniopropionate; Dimethylpropiothetin chloride; b-Dimethylsulphoniopropionate; Β-dimethylsulphoniopropionate; b-Dimethylsulfoniopropionate; 3-Dimethylsulfoniopropionate; Β-dimethylsulfoniopropionate; Dimethylsulphoniopropionate; Dimethyl-beta-propiothetin; Dimethylsulfoniopropionate; Dimethyl-β-propiothetin; Dimethyl-b-propiothetin; Dimethyl-propiothetin; Dimethylpropiothetin; beta-DMSP; DMPT; DMSP; S,S-Dimethyl-beta-propiothetin
数据库引用编号
17 个数据库交叉引用编号
- ChEBI: CHEBI:16457
- KEGG: C04022
- PubChem: 23736
- HMDB: HMDB0251405
- Metlin: METLIN66099
- Wikipedia: Dimethylsulfoniopropionate
- MetaCyc: SS-DIMETHYL-BETA-PROPIOTHETIN
- KNApSAcK: C00001355
- foodb: FDB030830
- chemspider: 22195
- CAS: 7314-30-9
- PMhub: MS000018169
- PubChem: 6728
- NIKKAJI: J227.511B
- KNApSAcK: 16457
- LOTUS: LTS0030709
- wikidata: Q3817447
分类词条
相关代谢途径
Reactome(0)
PlantCyc(0)
代谢反应
14 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(9)
- dimethylsulfoniopropanoate degradation I (cleavage):
DMSP ⟶ H+ + acrylate + dimethyl sulfide - superpathway of dimethylsulfoniopropanoate degradation:
DMSP ⟶ H+ + acrylate + dimethyl sulfide - dimethylsulfoniopropanoate degradation II (cleavage):
DMSP-CoA + H2O ⟶ 3-hydroxypropanoate + H+ + coenzyme A + dimethyl sulfide - dimethylsulfoniopropanoate degradation III (demethylation):
3-(methylsulfanyl)propanoate + H+ + a 5-methyltetrahydrofolate ⟶ DMSP + a tetrahydrofolate - dimethylsulfoniopropanoate biosynthesis II (Spartina):
3-dimethylsulfoniopropionaldehyde + H2O + NAD+ ⟶ DMSP + H+ + NADH - dimethylsulfoniopropanoate biosynthesis III (algae):
A + H2O + dimethylsulfonio-2-hydroxybutanoate ⟶ A(H2) + CO2 + DMSP - dimethylsulfoniopropanoate biosynthesis I (Wollastonia):
3-dimethylsulfoniopropionaldehyde + H2O + NAD+ ⟶ DMSP + H+ + NADH - dimethylsulfoniopropionate biosynthesis II (Spartina):
DMSP-amine + H2O + O2 ⟶ 3-dimethylsulfoniopropionaldehyde + H+ + ammonia + hydrogen peroxide - dimethylsulfoniopropionate biosynthesis I (Wollastonia):
H+ + S-methyl-L-methionine + a 2-oxo carboxylate ⟶ 3-dimethylsulfoniopropionaldehyde + CO2 + a proteinogenic amino acid
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(5)
- dimethylsulfoniopropanoate degradation I (cleavage):
DMSP ⟶ H+ + acrylate + dimethyl sulfide - dimethylsulfoniopropanoate degradation I (cleavage):
DMSP ⟶ H+ + acrylate + dimethyl sulfide - dimethylsulfoniopropanoate biosynthesis I (Wollastonia):
3-dimethylsulfoniopropionaldehyde + H2O + NAD+ ⟶ DMSP + H+ + NADH - dimethylsulfoniopropanoate biosynthesis II (Spartina):
3-dimethylsulfoniopropionaldehyde + H2O + NAD+ ⟶ DMSP + H+ + NADH - dimethylsulfoniopropanoate biosynthesis III (algae):
2-hydroxy-4-(methylsulfanyl)butanoate + H+ + a methylated methyl donor ⟶ a demethylated methyl donor + dimethylsulfonio-2-hydroxybutanoate
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
6 个相关的物种来源信息
- 9606 - Homo sapiens: -
- 2021211 - Indocypraea montana: 10.1104/PP.105.1.103
- 70838 - Pterocladiella capillacea: 10.1021/NP50056A023
- 32046 - Synechococcus elongatus: 10.1111/1462-2920.12899
- 35128 - Thalassiosira pseudonana: 10.1016/J.PROTIS.2019.05.004
- 101473 - Wollastonia biflora: 10.1104/PP.105.1.103
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
- Estelle E Clerc, Jean-Baptiste Raina, Johannes M Keegstra, Zachary Landry, Sammy Pontrelli, Uria Alcolombri, Bennett S Lambert, Valerio Anelli, Flora Vincent, Marta Masdeu-Navarro, Andreas Sichert, Frédéric De Schaetzen, Uwe Sauer, Rafel Simó, Jan-Hendrik Hehemann, Assaf Vardi, Justin R Seymour, Roman Stocker. Strong chemotaxis by marine bacteria towards polysaccharides is enhanced by the abundant organosulfur compound DMSP.
Nature communications.
2023 Dec; 14(1):8080. doi:
10.1038/s41467-023-43143-z. [PMID: 38057294] - Yu-Jing Chiou, Ya-Fan Chan, Sheng-Ping Yu, Chih-Ying Lu, Silver Sung-Yun Hsiao, Pei-Wen Chiang, Ting-Chang Hsu, Po-Yu Liu, Naohisa Wada, Yu Lee, Wann-Neng Jane, Der-Chuen Lee, Yu-Wen Huang, Sen-Lin Tang. Similar but different: Characterization of dddD gene-mediated DMSP metabolism among coral-associated Endozoicomonas.
Science advances.
2023 11; 9(47):eadk1910. doi:
10.1126/sciadv.adk1910. [PMID: 37992165] - Kathryn L Van Alstyne, Jennifer K Butler, Neal Smith. Airborne dimethyl sulfide (DMS) cues dimethylsulfoniopropionate (DMSP) increases in the intertidal green alga Ulva fenestrata.
Scientific reports.
2023 Mar; 13(1):4298. doi:
10.1038/s41598-023-30881-9. [PMID: 36922620] - Chun-Yang Li, Xiu-Juan Wang, Xiu-Lan Chen, Qi Sheng, Shan Zhang, Peng Wang, Mussa Quareshy, Branko Rihtman, Xuan Shao, Chao Gao, Fuchuan Li, Shengying Li, Weipeng Zhang, Xiao-Hua Zhang, Gui-Peng Yang, Jonathan D Todd, Yin Chen, Yu-Zhong Zhang. A novel ATP dependent dimethylsulfoniopropionate lyase in bacteria that releases dimethyl sulfide and acryloyl-CoA.
eLife.
2021 05; 10(?):. doi:
10.7554/elife.64045. [PMID: 33970104] - Cangsong Liao, Florian P Seebeck. In Vitro Reconstitution of Bacterial DMSP Biosynthesis.
Angewandte Chemie (International ed. in English).
2019 03; 58(11):3553-3556. doi:
10.1002/anie.201814662. [PMID: 30609124] - Noa Barak-Gavish, Miguel José Frada, Chuan Ku, Peter A Lee, Giacomo R DiTullio, Sergey Malitsky, Asaph Aharoni, Stefan J Green, Ron Rotkopf, Elena Kartvelishvily, Uri Sheyn, Daniella Schatz, Assaf Vardi. Bacterial virulence against an oceanic bloom-forming phytoplankter is mediated by algal DMSP.
Science advances.
2018 10; 4(10):eaau5716. doi:
10.1126/sciadv.aau5716. [PMID: 30397652] - Hélène Rousseau, Mathieu Rousseau-Gueutin, Xavier Dauvergne, Julien Boutte, Gaëlle Simon, Nathalie Marnet, Alain Bouchereau, Solène Guiheneuf, Jean-Pierre Bazureau, Jérôme Morice, Stéphane Ravanel, Francisco Cabello-Hurtado, Abdelkader Ainouche, Armel Salmon, Jonathan F Wendel, Malika L Ainouche. Evolution of DMSP (dimethylsulfoniopropionate) biosynthesis pathway: Origin and phylogenetic distribution in polyploid Spartina (Poaceae, Chloridoideae).
Molecular phylogenetics and evolution.
2017 09; 114(?):401-414. doi:
10.1016/j.ympev.2017.07.003. [PMID: 28694102] - Michel Lavoie, John A Raven, Maurice Levasseur. Energy cost and putative benefits of cellular mechanisms modulating buoyancy in aflagellate marine phytoplankton.
Journal of phycology.
2016 Apr; 52(2):239-51. doi:
10.1111/jpy.12390. [PMID: 27037589] - Stephanie G Gardner, Daniel A Nielsen, Olivier Laczka, Ronald Shimmon, Victor H Beltran, Peter J Ralph, Katherina Petrou. Dimethylsulfoniopropionate, superoxide dismutase and glutathione as stress response indicators in three corals under short-term hyposalinity stress.
Proceedings. Biological sciences.
2016 Feb; 283(1824):. doi:
10.1098/rspb.2015.2418. [PMID: 26865302] - Jessica Tout, Thomas C Jeffries, Katherina Petrou, Gene W Tyson, Nicole S Webster, Melissa Garren, Roman Stocker, Peter J Ralph, Justin R Seymour. Chemotaxis by natural populations of coral reef bacteria.
The ISME journal.
2015 Aug; 9(8):1764-77. doi:
10.1038/ismej.2014.261. [PMID: 25615440] - Lindsay Murdock, Tangi Burke, Chelsea Coumoundouros, Doreen E Culham, Charles E Deutch, James Ellinger, Craig H Kerr, Samantha M Plater, Eric To, Geordie Wright, Janet M Wood. Analysis of strains lacking known osmolyte accumulation mechanisms reveals contributions of osmolytes and transporters to protection against abiotic stress.
Applied and environmental microbiology.
2014 Sep; 80(17):5366-78. doi:
10.1128/aem.01138-14. [PMID: 24951793] - Heidi L Burdett, Victoria Keddie, Nicola MacArthur, Laurin McDowall, Jennifer McLeish, Eva Spielvogel, Angela D Hatton, Nicholas A Kamenos. Dynamic photoinhibition exhibited by red coralline algae in the Red Sea.
BMC plant biology.
2014 May; 14(?):139. doi:
10.1186/1471-2229-14-139. [PMID: 24885516] - Melissa Garren, Kwangmin Son, Jean-Baptiste Raina, Roberto Rusconi, Filippo Menolascina, Orr H Shapiro, Jessica Tout, David G Bourne, Justin R Seymour, Roman Stocker. A bacterial pathogen uses dimethylsulfoniopropionate as a cue to target heat-stressed corals.
The ISME journal.
2014 May; 8(5):999-1007. doi:
10.1038/ismej.2013.210. [PMID: 24335830] - Jan-Hendrik Hehemann, Adrienne Law, Lars Redecke, Alisdair B Boraston. The structure of RdDddP from Roseobacter denitrificans reveals that DMSP lyases in the DddP-family are metalloenzymes.
PloS one.
2014; 9(7):e103128. doi:
10.1371/journal.pone.0103128. [PMID: 25054772] - Ward Said-Ahmad, Alon Amrani. A sensitive method for the sulfur isotope analysis of dimethyl sulfide and dimethylsulfoniopropionate in seawater.
Rapid communications in mass spectrometry : RCM.
2013 Dec; 27(24):2789-96. doi:
10.1002/rcm.6751. [PMID: 24214865] - Mariusz A Bromke, Patrick Giavalisco, Lothar Willmitzer, Holger Hesse. Metabolic analysis of adaptation to short-term changes in culture conditions of the marine diatom Thalassiosira pseudonana.
PloS one.
2013; 8(6):e67340. doi:
10.1371/journal.pone.0067340. [PMID: 23799147] - Crystal C Lenky, Christopher J McEntyre, Michael Lever. Measurement of marine osmolytes in mammalian serum by liquid chromatography-tandem mass spectrometry.
Analytical biochemistry.
2012 Jan; 420(1):7-12. doi:
10.1016/j.ab.2011.09.013. [PMID: 21982861] - Barbara R Lyon, Peter A Lee, Jennifer M Bennett, Giacomo R DiTullio, Michael G Janech. Proteomic analysis of a sea-ice diatom: salinity acclimation provides new insight into the dimethylsulfoniopropionate production pathway.
Plant physiology.
2011 Dec; 157(4):1926-41. doi:
10.1104/pp.111.185025. [PMID: 22034629] - Astrid Spielmeyer, Georg Pohnert. Direct quantification of dimethylsulfoniopropionate (DMSP) with hydrophilic interaction liquid chromatography/mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2010 Dec; 878(31):3238-42. doi:
10.1016/j.jchromb.2010.09.031. [PMID: 21030323] - J D Todd, A R J Curson, C L Dupont, P Nicholson, A W B Johnston. The dddP gene, encoding a novel enzyme that converts dimethylsulfoniopropionate into dimethyl sulfide, is widespread in ocean metagenomes and marine bacteria and also occurs in some Ascomycete fungi.
Environmental microbiology.
2009 Jun; 11(6):1376-85. doi:
10.1111/j.1462-2920.2009.01864.x. [PMID: 19220400] - Kenji Nakajima, Akiko Yokoyama, Yoshiki Nakajima. Anticancer effects of a tertiary sulfonium compound, dimethylsulfoniopropionate, in green sea algae on Ehrlich ascites carcinoma-bearing mice.
Journal of nutritional science and vitaminology.
2009; 55(5):434-8. doi:
10.3177/jnsv.55.434. [PMID: 19926931] - Kenji Nakajima, Masaharu Minematsu, Yuuichi Miyamoto. Inhibition of the outgrowth and elongation of neurites from pheochromocytoma cells by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and preventive effects of dimethylsulfoniopropionate in the presence of nerve growth factor.
Journal of nutritional science and vitaminology.
2008 Apr; 54(2):176-80. doi:
10.3177/jnsv.54.176. [PMID: 18490849] - Andrew W B Johnston, Jonathan D Todd, Lei Sun, M Nefeli Nikolaidou-Katsaridou, Andrew R J Curson, Rachel Rogers. Molecular diversity of bacterial production of the climate-changing gas, dimethyl sulphide, a molecule that impinges on local and global symbioses.
Journal of experimental botany.
2008; 59(5):1059-67. doi:
10.1093/jxb/erm264. [PMID: 18281720] - Kenji Nakajima, Yuuichi Miyamoto. Effects of nerve growth factor and dimethylsulfoniopropionate in green sea algae on the outgrowth of neurites from pheochromocytoma cells.
Journal of nutritional science and vitaminology.
2007 Oct; 53(5):441-5. doi:
10.3177/jnsv.53.441. [PMID: 18079612] - Kenji Nakajima. Hyperhomocysteinemia can be ameliorated by dimethylsulfoniopropionate in place of folic acid in mice.
Journal of nutritional science and vitaminology.
2006 Feb; 52(1):61-5. doi:
10.3177/jnsv.52.61. [PMID: 16637231] - Marinus L Otte, Graham Wilson, James T Morris, Bridget M Moran. Dimethylsulphoniopropionate (DMSP) and related compounds in higher plants.
Journal of experimental botany.
2004 Aug; 55(404):1919-25. doi:
10.1093/jxb/erh178. [PMID: 15181109] - Aurélie Baliarda, Hervé Robert, Mohamed Jebbar, Carlos Blanco, Claire Le Marrec. Isolation and characterization of ButA, a secondary glycine betaine transport system operating in Tetragenococcus halophila.
Current microbiology.
2003 Oct; 47(4):347-51. doi:
10.1007/s00284-002-4017-x. [PMID: 14629018] - Y Gao, O M Schofield, T Leustek. Characterization of sulfate assimilation in marine algae focusing on the enzyme 5'-adenylylsulfate reductase.
Plant physiology.
2000 Jul; 123(3):1087-96. doi:
10.1104/pp.123.3.1087. [PMID: 10889258] - M G Kocsis, A D Hanson. Biochemical evidence for two novel enzymes in the biosynthesis of 3-dimethylsulfoniopropionate in Spartina alterniflora.
Plant physiology.
2000 Jul; 123(3):1153-61. doi:
10.1104/pp.123.3.1153. [PMID: 10889264] - M G Kocsis, K D Nolte, D Rhodes, T L Shen, D A Gage, A D Hanson. Dimethylsulfoniopropionate biosynthesis in Spartina alterniflora1. Evidence that S-methylmethionine and dimethylsulfoniopropylamine are intermediates.
Plant physiology.
1998 May; 117(1):273-81. doi:
10.1104/pp.117.1.273. [PMID: 9576797] - C Trossat, B Rathinasabapathi, E A Weretilnyk, T L Shen, Z H Huang, D A Gage, A D Hanson. Salinity promotes accumulation of 3-dimethylsulfoniopropionate and its precursor S-methylmethionine in chloroplasts.
Plant physiology.
1998 Jan; 116(1):165-71. doi:
10.1104/pp.116.1.165. [PMID: 9449841] - D A Gage, D Rhodes, K D Nolte, W A Hicks, T Leustek, A J Cooper, A D Hanson. A new route for synthesis of dimethylsulphoniopropionate in marine algae.
Nature.
1997 Jun; 387(6636):891-4. doi:
10.1038/43160. [PMID: 9202120] - M Vojtechová, A D Hanson, R A Muñoz-Clares. Betaine-aldehyde dehydrogenase from amaranth leaves efficiently catalyzes the NAD-dependent oxidation of dimethylsulfoniopropionaldehyde to dimethylsulfoniopropionate.
Archives of biochemistry and biophysics.
1997 Jan; 337(1):81-8. doi:
10.1006/abbi.1996.9731. [PMID: 8990271] - F James, L Paquet, S A Sparace, D A Gage, A D Hanson. Evidence implicating dimethylsulfoniopropionaldehyde as an intermediate in dimethylsulfoniopropionate biosynthesis.
Plant physiology.
1995 Aug; 108(4):1439-48. doi:
10.1104/pp.108.4.1439. [PMID: 7659747] - A D Hanson, J Rivoal, L Paquet, D A Gage. Biosynthesis of 3-dimethylsulfoniopropionate in Wollastonia biflora (L.) DC. Evidence that S-methylmethionine is an intermediate.
Plant physiology.
1994 May; 105(1):103-10. doi:
10.1104/pp.105.1.103. [PMID: 8029347] - K Nakajima. Dimethyl-beta-propiothetin, new potent resistive-agent against stress-induced gastric ulcers in rats.
Journal of nutritional science and vitaminology.
1991 Jun; 37(3):229-38. doi:
10.3177/jnsv.37.229. [PMID: 1919809] - A Puigvert, D Ruano. [Etiopathogenesis of so-called congenital hydronephrosis].
Journal d'urologie et de nephrologie.
1979 Jan; 85(1-2):1-12. doi:
NULL. [PMID: 439196] - D Trunkey, J Holcroft, M A Carpenter. Monitoring resuscitation of primates from hemorrhagic and septic shock.
JACEP.
1976 Apr; 5(4):249-52. doi:
10.1016/s0361-1124(76)80002-0. [PMID: 6816] - C WAGNER, E R STADTMAN. Bacterial fermentation of dimethyl-beta-propiothetin.
Archives of biochemistry and biophysics.
1962 Aug; 98(?):331-6. doi:
10.1016/0003-9861(62)90191-1. [PMID: 14004329] - R C GREENE. Biosynthesis of dimethyl-beta-propiothetin.
The Journal of biological chemistry.
1962 Jul; 237(?):2251-4. doi:
10.1016/s0021-9258(19)63427-7. [PMID: 13901535]
