beta-L-Rhamnose (ECMDB23078) (M2MDB003468)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (62)
Record Information
Version2.0
Creation Date2012-10-10 12:15:09 -0600
Update Date2015-06-03 17:25:52 -0600
Secondary Accession Numbers
  • ECMDB23078
Identification
Name:beta-L-Rhamnose
Descriptionbeta-L-Rhamnose is an anomer of alpha-L-rhamnose. It is a substrate of the E. coli enzyme L-rhamnose mutarotase. An anomer is a special type of epimer. It is one of two stereoisomers of a cyclic saccharide that differs only in its configuration at the hemiacetal or hemiketal carbon, also called the anomeric carbon.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • b-6-Deoxy-L-mannose
  • b-L-Mannomethylose
  • b-L-Rhamnose
  • Beta-6-Deoxy-L-mannose
  • Beta-L-Mannomethylose
  • L-Rhamnose
  • β-6-Deoxy-L-mannose
  • β-L-Mannomethylose
  • β-L-Rhamnose
Chemical Formula:C6H12O5
Weight:Average: 164.1565
Monoisotopic: 164.068473494
InChI Key:SHZGCJCMOBCMKK-YJRYQGEOSA-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:Not Available
IUPAC Name:(2S,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol
Traditional IUPAC Name:β-L-rhamnose
SMILES:C[C@@H]1O[C@H](O)[C@H](O)[C@H](O)[C@H]1O
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:Not Available
Charge:0
Melting point:Not Available
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
Polarizability15.32 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 > beta-L-Rhamnose
alpha-L-Rhamnose <> beta-L-Rhamnose
beta-L-Rhamnose > keto-L-rhamnulose + keto-L-rhamnulose
SMPDB Pathways:
fucose and rhamnose degradationPW000826 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_1) - 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:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID27586
HMDB IDNot Available
Pubchem Compound ID439730
Kegg IDC02338
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoRM4

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.