Trimethylamine N-oxide (BioDeep_00000002996)

 

Secondary id: BioDeep_00000400339, BioDeep_00001867959

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Toxin BioNovoGene_Lab2019


代谢物信息卡片


Trimethylamine N-oxide dihydrate

化学式: C3H9NO (75.0684)
中文名称: 无水三甲基胺 N-氧化物, 氧化三甲胺, 三甲胺 N-氧化物, 三甲胺氧化物
谱图信息: 最多检出来源 Homo sapiens(blood) 34.97%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Trimethylamine N-oxide. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/trimethylamine_n-oxide (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000002996). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CN(C)(C)=O
InChI: InChI=1/C3H9NO/c1-4(2,3)5/h1-3H3

描述信息

Trimethylamine N-oxide (TMAO) is an oxidation product of trimethylamine and a common metabolite in animals and humans. In particular, trimethylamine-N-oxide is biosynthesized endogenously from trimethylamine, which is derived from choline, which can be derived from dietary lecithin (phosphatidylcholines) or dietary carnitine. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood. TMAO is an osmolyte that the body will use to counteract the effects of increased concentrations of urea (due to kidney failure) and high levels can be used as a biomarker for kidney problems. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821). Fish odor syndrome or trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3) causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the persons sweat, urine, and breath, giving off a strong fishy odor. The concentration of TMAO in the blood increases after consuming foods containing carnitine or lecithin (phosphatidylcholines), if the bacteria that convert those substances to TMAO are present in the gut (PMID:23614584). High concentrations of carnitine are found in red meat, some energy drinks, and certain dietary supplements; lecithin is found in eggs and is commonly used as an ingredient in processed food. High levels of TMAO are found in many seafoods. Some types of normal gut bacteria (e.g. species of Acinetobacter) in the human gut convert dietary carnitine and dietary lecithin to TMAO (PMID:21475195). TMAO alters cholesterol metabolism in the intestines, in the liver and in arterial wall. When TMAO is present, cholesterol metabolism is altered and there is an increased deposition of cholesterol within, and decreased removal of cholesterol from, peripheral cells such as those in the artery wall (PMID:23563705). Urinary TMAO is a biomarker for the consumption of fish, especially cold-water fish. Trimethylamine N-oxide is found to be associated with maple syrup urine disease and propionic acidemia, which are inborn errors of metabolism. TMAO can also be found in Bacteroidetes, Ruminococcus (PMID:26687352).
Trimethylamine N-oxide (TMAO) is an oxidation product of trimethylamine and a common metabolite in animals and humans. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood. TMAO is an osmolyte that the body will use to counter-act the effects of increased concentrations of urea (due to kidney failure) and can be used as a biomarker for kidney problems. Fish odor syndrome or trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3) causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the persons sweat, urine, and breath, giving off a strong fishy odor.; Trimethylamine N-oxide, also known by several other names and acronyms, is the organic compound with the formula (CH3)3NO. This colorless solid is usually encountered as the dihydrate. It is an oxidation product of trimethylamine and a common metabolite in animals. It is an osmolyte found in saltwater fish, sharks and rays, molluscs, and crustaceans. Along with free amino acids, it reduces the 3\\\% salinity of seawater to about 1\\\% of dissolved solids inside cells. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood.; Trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3),, causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the persons sweat, urine, and breath, giving off a strong fishy odor. Urinary TMAO is a biomarker for the consumption of fish, especially cold-water fish.
Acquisition and generation of the data is financially supported in part by CREST/JST.
D009676 - Noxae > D016877 - Oxidants
KEIO_ID T051
Trimethylamine N-oxide is a gut microbe-dependent metabolite of dietary choline and other trimethylamine-containing nutrients. Trimethylamine N-oxide induces inflammation by activating the ROS/NLRP3 inflammasome. Trimethylamine N-oxide also accelerates fibroblast-myofibroblast differentiation and induces cardiac fibrosis by activating the TGF-β/smad2 signaling pathway[1][2][3].

同义名列表

19 个代谢物同义名

Trimethylamine N-oxide dihydrate; N,N-Dimethylmethanamine N-oxide; N,N-dimethylmethanamine oxide; Trimethylammonium oxide; Trimethylamine N-oxide; Trimethylamine-N-oxide; Trimethylamine oxide; Trimethylaminoxid; Trimethyloxamine; Me3n(+)O(-); TMA-oxide; (CH3)3NO; N(CH3)3O; Me3n(O); Triox; TMAO; Trimethylamine-N-oxide; Trimethylamine N-oxide; Trimethylamine oxide



数据库引用编号

29 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(3)

PlantCyc(0)

代谢反应

75 个相关的代谢反应过程信息。

Reactome(54)

BioCyc(19)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(2)

  • N-Oxide Electron Transfer: Electron + Formic acid + Hydrogen Ion + menaquinone-8 ⟶ Carbon dioxide + Hydrogen Ion + Menaquinol 8
  • N-Oxide Electron Transfer: Electron + Hydrogen Ion + Menaquinol 8 + Trimethylamine N-oxide ⟶ Hydrogen Ion + Trimethylamine + Water + menaquinone-8

PharmGKB(0)

4 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 6 ALB, CASP1, CST3, IL18, NOS3, TJP1
Peripheral membrane protein 3 GORASP1, HSD17B6, TJP1
Endosome membrane 1 LDLR
Endoplasmic reticulum membrane 4 CYP7A1, FMO1, FMO3, HSP90B1
Nucleus 5 ALB, HSP90B1, NOS3, NR1H4, TJP1
cytosol 7 ALB, CASP1, GPT, HSP90B1, IL18, NOS3, TJP1
centrosome 1 ALB
nucleoplasm 2 NOS3, NR1H4
RNA polymerase II transcription regulator complex 1 NR1H4
Cell membrane 3 CASP1, LDLR, TJP1
Cytoplasmic side 2 GORASP1, TJP1
Early endosome membrane 1 HSD17B6
Golgi apparatus membrane 1 GORASP1
cell junction 1 TJP1
cell surface 1 LDLR
Golgi apparatus 5 ALB, CST3, GORASP1, LDLR, NOS3
Golgi membrane 3 GORASP1, INS, NOS3
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 IL18
Lysosome 1 LDLR
plasma membrane 5 CASP1, CST3, LDLR, NOS3, TJP1
Membrane 2 HSP90B1, LDLR
apical plasma membrane 1 TJP1
basolateral plasma membrane 2 LDLR, TJP1
caveola 1 NOS3
extracellular exosome 5 ALB, CST3, GPT, HSP90B1, LYZ
Lumenal side 1 HSD17B6
endoplasmic reticulum 6 ALB, CST3, FMO1, FMO3, HSD17B6, HSP90B1
extracellular space 8 ALB, CCL2, CST3, IL10, IL18, IL6, INS, LYZ
perinuclear region of cytoplasm 2 HSP90B1, NOS3
Cell junction, tight junction 1 TJP1
adherens junction 1 TJP1
apicolateral plasma membrane 1 TJP1
bicellular tight junction 1 TJP1
gap junction 1 TJP1
intercalated disc 1 TJP1
intercellular canaliculus 1 TJP1
mitochondrion 1 TJP1
protein-containing complex 4 ALB, CASP1, HSP90B1, TJP1
intracellular membrane-bounded organelle 3 CYP7A1, FMO3, HSD17B6
Microsome membrane 3 CYP7A1, FMO3, HSD17B6
Single-pass type I membrane protein 1 LDLR
Secreted 7 ALB, CCL2, CST3, IL10, IL18, IL6, INS
extracellular region 9 ALB, CCL2, CST3, HSP90B1, IL10, IL18, IL6, INS, LYZ
Single-pass membrane protein 4 CYP7A1, FMO1, FMO3, LDLR
anchoring junction 1 ALB
external side of plasma membrane 1 LDLR
low-density lipoprotein particle 1 LDLR
nucleolus 1 CASP1
midbody 1 HSP90B1
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
Early endosome 1 LDLR
Membrane, clathrin-coated pit 1 LDLR
apical part of cell 2 LDLR, TJP1
clathrin-coated pit 1 LDLR
vesicle 1 CST3
focal adhesion 1 HSP90B1
microtubule 1 CASP1
cis-Golgi network 1 GORASP1
collagen-containing extracellular matrix 1 HSP90B1
NLRP3 inflammasome complex 1 CASP1
Late endosome 1 LDLR
receptor complex 2 LDLR, NR1H4
ciliary basal body 1 ALB
chromatin 1 NR1H4
cell projection 1 TJP1
cytoskeleton 1 NOS3
Cell projection, podosome 1 TJP1
podosome 1 TJP1
[Isoform 3]: Nucleus 1 NR1H4
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
Endomembrane system 1 LDLR
endosome lumen 1 INS
sorting endosome 1 LDLR
Melanosome 1 HSP90B1
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
euchromatin 1 NR1H4
sperm plasma membrane 1 HSP90B1
ficolin-1-rich granule lumen 1 CST3
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 6 ALB, CST3, FMO1, HSP90B1, IL6, INS
platelet alpha granule lumen 1 ALB
specific granule lumen 1 LYZ
tertiary granule lumen 2 CST3, LYZ
endocytic vesicle membrane 1 NOS3
transport vesicle 1 INS
tight junction 1 TJP1
azurophil granule lumen 1 LYZ
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GORASP1, INS
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
AIM2 inflammasome complex 1 CASP1
clathrin-coated endocytic vesicle membrane 1 LDLR
Sarcoplasmic reticulum lumen 1 HSP90B1
[Isoform 2]: Nucleus 1 NR1H4
[Isoform 1]: Nucleus 1 NR1H4
endolysosome membrane 1 LDLR
apical junction complex 1 TJP1
canonical inflammasome complex 1 CASP1
somatodendritic compartment 1 LDLR
[Isoform 4]: Nucleus 1 NR1H4
endocytic vesicle lumen 1 HSP90B1
PCSK9-LDLR complex 1 LDLR
interleukin-6 receptor complex 1 IL6
endoplasmic reticulum chaperone complex 1 HSP90B1
IPAF inflammasome complex 1 CASP1
NLRP1 inflammasome complex 1 CASP1
protease inhibitor complex 1 CASP1
ciliary transition fiber 1 ALB


文献列表

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  • Mingxiao Luo, Peng Chen, Ye Tian, Norbu Rigzin, Jigme Sonam, Feihu Shang, Chuang Tai, Tingting Li, Haiquan Sang. Hif-1α expression targets the TMA/Fmo3/TMAO axis to participate in gallbladder cholesterol stone formation in individuals living in plateau regions. Biochimica et biophysica acta. Molecular basis of disease. 2024 Jun; 1870(5):167188. doi: 10.1016/j.bbadis.2024.167188. [PMID: 38657913]
  • Chenyu Jiang, Song Wang, Yihan Wang, Ketao Wang, Chunying Huang, Fei Gao, Huang Peng Hu, Yangyong Deng, Wen Zhang, Jian Zheng, Jianqin Huang, Yan Li. Polyphenols from hickory nut reduce the occurrence of atherosclerosis in mice by improving intestinal microbiota and inhibiting trimethylamine N-oxide production. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Jun; 128(?):155349. doi: 10.1016/j.phymed.2024.155349. [PMID: 38522315]
  • Natalia G Vallianou, Dimitris Kounatidis, Sotiria Psallida, Fotis Panagopoulos, Theodora Stratigou, Eleni Geladari, Irene Karampela, Dimitrios Tsilingiris, Maria Dalamaga. The Interplay Between Dietary Choline and Cardiometabolic Disorders: A Review of Current Evidence. Current nutrition reports. 2024 06; 13(2):152-165. doi: 10.1007/s13668-024-00521-3. [PMID: 38427291]
  • Ryohei Tanaka-Kanegae, Hiroyuki Kimura, Koichiro Hamada. Pharmacokinetics of soy-derived lysophosphatidylcholine compared with that of glycerophosphocholine: a randomized controlled trial. Bioscience, biotechnology, and biochemistry. 2024 May; 88(6):648-655. doi: 10.1093/bbb/zbae031. [PMID: 38490741]
  • Qiao Jin, Chiyuan Zhang, Ran Chen, Luping Jiang, Hongli Li, Pengcui Wu, Liang Li. Quinic acid regulated TMA/TMAO-related lipid metabolism and vascular endothelial function through gut microbiota to inhibit atherosclerotic. Journal of translational medicine. 2024 Apr; 22(1):352. doi: 10.1186/s12967-024-05120-y. [PMID: 38622667]
  • Caleigh M Sawicki, Lorena S Pacheco, Sona Rivas-Tumanyan, Zheyi Cao, Danielle E Haslam, Liming Liang, Katherine L Tucker, Kaumudi Joshipura, Shilpa N Bhupathiraju. Association of Gut Microbiota-Related Metabolites and Type 2 Diabetes in Two Puerto Rican Cohorts. Nutrients. 2024 Mar; 16(7):. doi: 10.3390/nu16070959. [PMID: 38612993]
  • Xinyi Shen, Curtis Tilves, Hyunju Kim, Toshiko Tanaka, Adam P Spira, Chee W Chia, Sameera A Talegawkar, Luigi Ferrucci, Noel T Mueller. Plant-based diets and the gut microbiome: findings from the Baltimore Longitudinal Study of Aging. The American journal of clinical nutrition. 2024 Mar; 119(3):628-638. doi: 10.1016/j.ajcnut.2024.01.006. [PMID: 38218318]
  • Xiao-Yue Li, Zhu-Lin Yu, Ying-Cai Zhao, Dan-Dan Wang, Chang-Hu Xue, Tian-Tian Zhang, Yu-Ming Wang. Gut Microbiota Metabolite TMA May Mediate the Effects of TMAO on Glucose and Lipid Metabolism in C57BL/6J Mice. Molecular nutrition & food research. 2024 Mar; 68(6):e2300443. doi: 10.1002/mnfr.202300443. [PMID: 38456781]
  • Rui Sun, Zedong Cheng, Di Li, Jingyao Yin. Effects of Lizhong Tongmai acupuncture on TMAO, CD36 expression, and cholesterol deposition in atherosclerotic mice. Zhongguo zhen jiu = Chinese acupuncture & moxibustion. 2024 Feb; 44(2):169-174. doi: 10.13703/j.0255-2930.20230606-0001. [PMID: 38373762]
  • Wangwang Huang, Yizhuo Hua, Fan Wang, Jia Xu, Lv Yuan, Zhao Jing, Weimin Wang, Yuhua Zhao. Dietary betaine and/or TMAO affect hepatic lipid accumulation and glycometabolism of Megalobrama amblycephala exposed to a high-carbohydrate diet. Fish physiology and biochemistry. 2024 Feb; 50(1):59-75. doi: 10.1007/s10695-022-01160-7. [PMID: 36580207]
  • Huafang Ding, Jianhui Liu, Zixing Chen, Shouhe Huang, Chi Yan, Erika Kwek, Zouyan He, Hanyue Zhu, Zhen-Yu Chen. Protocatechuic acid alleviates TMAO-aggravated atherosclerosis via mitigating inflammation, regulating lipid metabolism, and reshaping gut microbiota. Food & function. 2024 Jan; 15(2):881-893. doi: 10.1039/d3fo04396g. [PMID: 38165856]
  • Lei Liu, Huifang Xu, Jian Wang, Haiyan Wang, Saisai Ren, Qian Huang, Mingyan Zhang, Hui Zhou, Chunyan Yang, Lu Jia, Yu Huang, Hao Zhang, Yanling Tao, Ying Li, Yanan Min. Trimethylamine-N-oxide (TMAO) and basic fibroblast growth factor (bFGF) are possibly involved in corticosteroid resistance in adult patients with immune thrombocytopenia. Thrombosis research. 2024 Jan; 233(?):25-36. doi: 10.1016/j.thromres.2023.11.003. [PMID: 37988847]
  • Ziyan Wang, Chengxin Liu, Jiaming Wei, Hui Yuan, Min Shi, Fei Zhang, Qinghua Zeng, Aisi Huang, Lixin Du, Ya Li, Zhihua Guo. Network and Experimental Pharmacology on Mechanism of Yixintai Regulates the TMAO/PKC/NF-κB Signaling Pathway in Treating Heart Failure. Drug design, development and therapy. 2024; 18(?):1415-1438. doi: 10.2147/dddt.s448140. [PMID: 38707614]
  • Chih-Yao Hou, Yu-Wei Chen, Sulfath Hakkim Hazeena, You-Lin Tain, Chang-Wei Hsieh, De-Quan Chen, Rou-Yun Liu, Ming-Kuei Shih. Cardiovascular risk of dietary trimethylamine oxide precursors and the therapeutic potential of resveratrol and its derivatives. FEBS open bio. 2023 Dec; ?(?):. doi: 10.1002/2211-5463.13762. [PMID: 38151750]
  • ZhiSheng Luo, XiaoChen Yu, Chao Wang, HaiYan Zhao, Xinming Wang, XiuRu Guan. Trimethylamine N-oxide promotes oxidative stress and lipid accumulation in macrophage foam cells via the Nrf2/ABCA1 pathway. Journal of physiology and biochemistry. 2023 Nov; ?(?):. doi: 10.1007/s13105-023-00984-y. [PMID: 37932654]
  • Xiuqi Sun, Anbang Zhang, Bo Pang, Yuanhua Wu, Jingyu Shi, Ning Zhang, Tao Ye. Electroacupuncture pretreatment alleviates spasticity after stroke in rats by inducing the NF-κB/NLRP3 signaling pathway and the gut-brain axis. Brain research. 2023 Oct; 1822(?):148643. doi: 10.1016/j.brainres.2023.148643. [PMID: 37884180]
  • Shan Huang, Si Ying Lim, Sock Hwee Tan, Mark Y Chan, Wuzhong Ni, Sam Fong Yau Li. Targeted Plasma Metabolomics Reveals Association of Acute Myocardial Infarction Risk with the Dynamic Balance between Trimethylamine-N-oxide, Betaine, and Choline. Journal of agricultural and food chemistry. 2023 Oct; ?(?):. doi: 10.1021/acs.jafc.2c08241. [PMID: 37781984]
  • Tu'erhong Fei'erdun, Weimin Zhang, Keyoumu Yilihamujiang, Mingming Zhang, Mangyuan Wang. [Correlation Between Plasma Trimethylamine N-Oxide and Lipid Levels in Hyperlipidemic Patients]. Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition. 2023 Sep; 54(5):1030-1034. doi: 10.12182/20230960109. [PMID: 37866964]
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