alpha-L-Rhamnose (ECMDB00849) (M2MDB000192)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)Transporters (6)XML
Proteins (68)
Record Information
Version2.0
Creation Date2012-05-31 13:01:34 -0600
Update Date2015-09-13 12:56:09 -0600
Secondary Accession Numbers
  • ECMDB00849
Identification
Name:alpha-L-Rhamnose
DescriptionRhamnose is a methylpentose whose L- isomer is found naturally in many plant glycosides and some gram-negative bacterial lipopolysaccharides.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 6-Deoxy-L(+)-mannose
  • 6-Deoxy-L-Mannopyranose
  • 6-Deoxy-L-mannose
  • 6-Deoxy-Mannose
  • 6-Deoxyhexopyranose
  • 6-Deoxyhexose
  • 6-Deoxymannose
  • a-L-Rhamnose
  • Isodulcit
  • Isodulcitol
  • L(+)-Rhamnose
  • L(+)-Rhamnose monohydrate
  • L(+)-Rhamnose monohydric acid
  • L-(+)-Rhamnose
  • L-(+)-Rhamnose 1-hydrate
  • L-(+)-Rhamnose 1-hydric acid
  • L-(+)-Rhamnose Hydrate = 6-Deoxy-L-mannose Monohydrate
  • L-(+)-Rhamnose Hydric acid = 6-Deoxy-L-mannose Monohydrate
  • L-(+)-Rhamnose hydric acid = 6-deoxy-L-mannose monohydric acid
  • L-(+)-Rhamnose monohydrate
  • L-(+)-Rhamnose monohydric acid
  • L-Mannomethylose
  • L-Rhamnopyranose
  • L-Rhamnose
  • L-Rhamnose for biochemistry
  • L-Rhamnose Monohydrate
  • L-Rhamnose Monohydric acid
  • Locaose
  • Mono(6-deoxy-b-L-mannopyranosyl) ester
  • Mono(6-deoxy-beta-L-mannopyranosyl) ester
  • mono(6-Deoxy-β-L-mannopyranosyl) ester
  • P-(6-Deoxy-b-L-mannopyranosyl) ester
  • P-(6-Deoxy-beta-L-mannopyranosyl) ester
  • P-(6-Deoxy-β-L-mannopyranosyl) ester
  • Rhamnopyranose
  • Rhamnose
  • Rhamnosemonohydrate
  • Rhamnosemonohydric acid
  • UDP-Rhamnose
  • Uridine 5-pyrophosphate
  • Uridine 5-pyrophosphoric acid
  • Uridine diphosphate rhamnose
  • Uridine diphosphoric acid rhamnose
  • α-L-Rhamnose
Chemical Formula:C6H12O5
Weight:Average: 164.1565
Monoisotopic: 164.068473494
InChI Key:SHZGCJCMOBCMKK-HGVZOGFYSA-N
InChI:InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3-,4+,5+,6+/m0/s1
CAS number:3615-41-6
IUPAC Name:(2R,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol
Traditional IUPAC Name:α-L-rhamnopyranose
SMILES:[H][C@@]1(C)O[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:122 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility827 g/LALOGPS
logP-2.4ALOGPS
logP-1.9ChemAxon
logS0.7ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.38 m³·mol⁻¹ChemAxon
Polarizability15.26 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
alpha-L-Rhamnose + L-Rhamnose <> L-Rhamnulose
alpha-L-Rhamnose <> L-Rhamnulose
alpha-L-Rhamnose &beta;-L-rhamnose
alpha-L-Rhamnose > L-Rhamnulose
alpha-L-Rhamnose > beta-L-Rhamnose
alpha-L-Rhamnose <> beta-L-Rhamnose
SMPDB Pathways:
fucose and rhamnose degradationPW000826 ThumbThumb?image type=greyscaleThumb?image type=simple
inner membrane transportPW000786 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Fructose and mannose metabolism ec00051
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1900000000-73abedcfedce730de924View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1900000000-5f2bd8fc908e0f2d17d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-9000000000-4ae8072a5651434f44b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3900000000-e7a20de995c932bdb5d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-6900000000-03f10dd2373a0985cc0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1ef6b887ff1a4477de1fView in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Cambronero Sanchez, Miguel; Garcia Ruiz, Pedro Antonio. Preparation of high-purity L-rhamnose from rhamnoglucosides. Span. (1997), 7 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16055
HMDB IDHMDB00849
Pubchem Compound ID840
Kegg IDC02476
ChemSpider ID23642
WikipediaRhamnose
BioCyc IDRHAMNOSE
EcoCyc IDRHAMNOSE
Ligand ExpoRAM

Enzymes

Protein Details
1. L-rhamnose isomerase
General function:
Involved in L-rhamnose isomerase activity
Specific function:
L-rhamnose = L-rhamnulose
Gene Name:
rhaA
Uniprot ID:
P32170
Molecular weight:
47199
Reactions
L-rhamnose = L-rhamnulose.
Protein Details
2. L-rhamnose mutarotase
General function:
Involved in protein binding
Specific function:
Involved in the anomeric conversion of L-rhamnose
Gene Name:
rhaM
Uniprot ID:
P32156
Molecular weight:
12265
Reactions
Alpha-L-rhamnose = beta-L-rhamnose.

Transporters

Protein Details
1. Sugar efflux transporter C
General function:
Involved in transmembrane transport
Specific function:
Involved in the efflux of sugars. The physiological role may be the detoxification of non-metabolizable sugar analogs
Gene Name:
setC
Uniprot ID:
P31436
Molecular weight:
43493
Protein Details
2. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
3. Outer membrane pore protein E
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
Protein Details
4. L-rhamnose-proton symporter
General function:
Involved in rhamnose transmembrane transporter activity
Specific function:
Uptake of L-rhamnose across the boundary membrane with the concomitant transport of protons into the cell (symport system). Can also transport L-mannose and L-xylose, but at reduced rates
Gene Name:
rhaT
Uniprot ID:
P27125
Molecular weight:
37319
Protein Details
5. Outer membrane protein F
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
Protein Details
6. Outer membrane protein C
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368