Deoxythymidine diphosphate-L-rhamnose (BioDeep_00000000817)
Secondary id: BioDeep_00000005125
human metabolite PANOMIX_OTCML-2023 Endogenous
代谢物信息卡片
化学式: C16H26N2O15P2 (548.0808386)
中文名称:
谱图信息:
最多检出来源 Macaca mulatta(otcml) 0.66%
分子结构信息
SMILES: CC1C(C(C(C(O1)OP(=O)(O)OP(=O)(O)OCC2C(CC(O2)N3C=C(C(=O)NC3=O)C)O)O)O)O
InChI: InChI=1S/C16H26N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-13,15,19-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8+,9+,10+,11-,12-,13+,15+/m0/s1
描述信息
Deoxythymidine diphosphate-L-rhamnose (dTDP-L-rhamnose) is the precursor of L-rhamnose, a saccharide required for the virulence of some pathogenic bacteria. In gram-negative bacteria such as Salmonella enterica, Vibrio cholerae, or Escherichia coli 075:K5, L-rhamnose is an important residue in the O-antigen of lipopolysaccharides, which are essential for resistance to serum killing and colonization. In gram-positive bacteria such as streptococci, the capsule is a recognized virulence factor. For example, L-rhamnose is known to be present in the capsule of Streptococcus suis, a causative agent of meningitis in humans. In Streptococcus mutans, L-rhamnose containing polysaccharides have been implicated in tooth surface colonization and adherence to kidney, muscle, and heart tissues. In mycobacteria, L-rhamnose is fundamental to the structural integrity of the cell wall since it connects the inner peptidoglycan layer to the arabinogalactan polysaccharides. dTDP-L-rhamnose is synthesized from glucose-1-phosphate and deoxythymidine triphosphate (dTTP) via a pathway involving four distinct enzymes. Whereas common sugars such as glucose, fructose, and mannose are all D-configured, bacteria commonly utilize the L-configured carbohydrates in pharmacologically active compounds and their cell-wall structures. The bacterial cell wall is unique to bacteria; neither the cell wall nor the enzymes and chemical intermediates in its formation have analogues in humans. The enzymes involved in dTDP-L-rhamnose synthesis are potential targets for the design of new therapeutic agents (PMID: 10802738, 12773151).
2-deoxy-thymidine-beta-l-rhamnose, also known as dtdp-6-deoxy-L-mannose or thymidine diphosphate-L-rhamnose, is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. 2-deoxy-thymidine-beta-l-rhamnose is soluble (in water) and a moderately acidic compound (based on its pKa). 2-deoxy-thymidine-beta-l-rhamnose can be found in a number of food items such as black salsify, dill, roman camomile, and tea leaf willow, which makes 2-deoxy-thymidine-beta-l-rhamnose a potential biomarker for the consumption of these food products.
DTDP-beta-L-rhamnose is the beta-anomer of dTDP-L-rhamnose. It has a role as an Escherichia coli metabolite. It is functionally related to a dTDP-L-mannose. It is a conjugate acid of a dTDP-6-deoxy-beta-L-mannose(2-).
Deoxythymidine diphosphate-L-rhamnose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
The beta-anomer of dTDP-L-rhamnose.
同义名列表
30 个代谢物同义名
[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl (2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name); {[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid; [hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] [(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl] hydrogen phosphate; Thymidine 5-(trihydrogen diphosphoric acid), p-(6-deoxy-beta-L-mannopyranosyl) ester; Thymidine 5-(trihydrogen diphosphoric acid), p-(6-deoxy-b-L-mannopyranosyl) ester; Thymidine 5-(trihydrogen diphosphoric acid), p-(6-deoxy-β-L-mannopyranosyl) ester; Thymidine 5-(trihydrogen diphosphate), P-(6-deoxy-beta-L-mannopyranosyl) ester; Thymidine 5-(trihydrogen diphosphate), p-(6-deoxy-b-L-mannopyranosyl) ester; Thymidine 5-(trihydrogen diphosphate), p-(6-deoxy-β-L-mannopyranosyl) ester; thymidine 5-[3-(6-deoxy-beta-L-mannopyranosyl) dihydrogen diphosphate]; Deoxythymidine diphosphoric acid-L-rhamnose; Thymidine diphosphoric acid-L-rhamnose; Deoxythymidine diphosphate-l-rhamnose; Deoxythymidine diphosphate rhamnose; Thymidine-5-diphosphate-L-rhamnose; 2-Deoxy-thymidine-beta-L-rhamnose; thymidine diphosphate-L-rhamnose; thymidine diphosphate rhamnose; dTDP-6-deoxy-beta-L-mannose; dTDP-6-Deoxy-b-L-mannose; dTDP-6-Deoxy-β-L-mannose; dTDP-6-deoxy-L-mannose; dTDP-beta-L-rhamnose; dTDP-L-beta-rhamnose; dTDP-Β-L-rhamnose; dTDP-b-L-Rhamnose; dTDP-L-rhamnose; dTDP L-rhamnose; TDP-L-Rhamnose; TDP-Rhamnose
数据库引用编号
20 个数据库交叉引用编号
- ChEBI: CHEBI:15774
- KEGG: C03319
- PubChem: 121966
- HMDB: HMDB0006354
- Metlin: METLIN58402
- DrugBank: DB03723
- MeSH: thymidine diphosphate rhamnose
- ChemIDplus: 0002147593
- MetaCyc: DTDP-RHAMNOSE
- KNApSAcK: C00007662
- foodb: FDB030838
- chemspider: 108806
- CAS: 2147-59-3
- medchemexpress: HY-N11102
- MetaboLights: MTBLC15774
- PubChem: 6171
- PDB-CCD: TRH
- 3DMET: B04888
- NIKKAJI: J818.234E
- RefMet: dTDP-beta-L-rhamnose
分类词条
相关代谢途径
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代谢反应
0 个相关的代谢反应过程信息。
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1 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。
文献列表
- Edgardo Jofré, Antonio Lagares, Gladys Mori. Disruption of dTDP-rhamnose biosynthesis modifies lipopolysaccharide core, exopolysaccharide production, and root colonization in Azospirillum brasilense.
FEMS microbiology letters.
2004 Feb; 231(2):267-75. doi:
10.1016/s0378-1097(04)00003-5
. [PMID: 14987774] - Y Ma, R J Stern, M S Scherman, V D Vissa, W Yan, V C Jones, F Zhang, S G Franzblau, W H Lewis, M R McNeil. Drug targeting Mycobacterium tuberculosis cell wall synthesis: genetics of dTDP-rhamnose synthetic enzymes and development of a microtiter plate-based screen for inhibitors of conversion of dTDP-glucose to dTDP-rhamnose.
Antimicrobial agents and chemotherapy.
2001 May; 45(5):1407-16. doi:
10.1128/aac.45.5.1407-1416.2001
. [PMID: 11302803]