Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:36:36 UTC |
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Update date | 2015-07-21 06:57:55 UTC |
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Primary ID | FDB023902 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Deoxythymidine diphosphate-L-rhamnose |
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Description | Deoxythymidine diphosphate (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 for 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 in 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) [HMDB] |
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CAS Number | 2147-59-3 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C16H26N2O15P2 |
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IUPAC 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}({[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid |
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InChI Identifier | 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 |
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InChI Key | ZOSQFDVXNQFKBY-CZRCVJRHSA-N |
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Isomeric SMILES | C[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N2C=C(C)C(=O)NC2=O)[C@H](O)[C@H](O)[C@H]1O |
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Average Molecular Weight | 548.3296 |
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Monoisotopic Molecular Weight | 548.080841196 |
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Classification |
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Description | Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Pyrimidine nucleotides |
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Sub Class | Pyrimidine nucleotide sugars |
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Direct Parent | Pyrimidine nucleotide sugars |
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Alternative Parents | |
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Substituents | - Pyrimidine nucleotide sugar
- Pyrimidine 2'-deoxyribonucleoside diphosphate
- Pentose phosphate
- Monosaccharide phosphate
- Organic pyrophosphate
- Monoalkyl phosphate
- Pyrimidone
- Hydropyrimidine
- Phosphoric acid ester
- Monosaccharide
- Organic phosphoric acid derivative
- Oxane
- Alkyl phosphate
- Pyrimidine
- Heteroaromatic compound
- Vinylogous amide
- Tetrahydrofuran
- Urea
- Lactam
- Secondary alcohol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Polyol
- Organonitrogen compound
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organic nitrogen compound
- Organic oxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: Source: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Deoxythymidine diphosphate-L-rhamnose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0036-6922340000-5b7bbefa46231e0401e7 | Spectrum | Predicted GC-MS | Deoxythymidine diphosphate-L-rhamnose, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00bc-8441509000-f72396e274d70b76dce1 | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-a235a91a2d2afe7e5b0e | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-3921000000-f27277a5a22d8b1a6e62 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-4900000000-385a0d128de7afa0ef56 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0f6t-3303290000-8fb8bdb50a4d4dd37d52 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ufu-5915010000-0710c988c191bfa8f10b | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a6u-4901000000-ac82c124189fc9d5bf1d | 2015-09-15 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 388998 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C03319 |
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Pubchem Compound ID | 439975 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 35452 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB06354 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 41621 |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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