MiMeDB: Showing metabocard for dTDP-beta-L-rhamnose (MMDBc0054471)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:14:17 UTC

Update Date

2022-08-27 02:18:06 UTC

Metabolite ID

MMDBc0054471

Metabolite Identification

Common Name

dTDP-beta-L-rhamnose

Description

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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₁₆H₂₆N₂O₁₅P₂

Average Mass

548.3296

Monoisotopic Mass

548.080841196

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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

InChI Key

ZOSQFDVXNQFKBY-CGAXJHMRSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Proteobacteria	7	Human ; Human feces; Human feces; pleural fluid plaque; bal
Bacteria	Actinobacteria	5	Human
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Giraud MF, Leonard GA, Field RA, Berlind C, Naismith JH: RmlC, the third enzyme of dTDP-L-rhamnose pathway, is a new class of epimerase. Nat Struct Biol. 2000 May;7(5):398-402. doi: 10.1038/75178. [PubMed:10802738 ]
Dong C, Beis K, Giraud MF, Blankenfeldt W, Allard S, Major LL, Kerr ID, Whitfield C, Naismith JH: A structural perspective on the enzymes that convert dTDP-d-glucose into dTDP-l-rhamnose. Biochem Soc Trans. 2003 Jun;31(Pt 3):532-6. doi: 10.1042/bst0310532. [PubMed:12773151 ]

Showing metabocard for dTDP-beta-L-rhamnose (MMDBc0054471)

MOL for #<Metabolite:0x00007f1241036ad8>

3D MOL for #<Metabolite:0x00007f1241036ad8>

3D SDF for #<Metabolite:0x00007f1241036ad8>

3D-SDF for #<Metabolite:0x00007f1241036ad8>

PDB for #<Metabolite:0x00007f1241036ad8>

3D PDB for #<Metabolite:0x00007f1241036ad8>

SMILES for #<Metabolite:0x00007f1241036ad8>

INCHI for #<Metabolite:0x00007f1241036ad8>

Structure for #<Metabolite:0x00007f1241036ad8>

3D Structure for #<Metabolite:0x00007f1241036ad8>