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Record Information
Version	2.0
Creation Date	2012-05-31 13:01:34 -0600
Update Date	2015-09-13 12:56:09 -0600
Secondary Accession Numbers	ECMDB00849
Identification
Name:	alpha-L-Rhamnose
Description	Rhamnose is a methylpentose whose L- isomer is found naturally in many plant glycosides and some gram-negative bacterial lipopolysaccharides.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaa78544c> Close
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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Hexoses
Alternative Parents	Oxanes Secondary alcohols Hemiacetals Polyols Oxacyclic compounds Hydrocarbon derivatives
Substituents	Hexose monosaccharide Oxane Secondary alcohol Hemiacetal Oxacycle Organoheterocyclic compound Polyol Hydrocarbon derivative Alcohol Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	L-rhamnopyranose (CHEBI:27907 )
Physical Properties
State:	Solid
Charge:	0
Melting point:	122 °C
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 827 g/L ALOGPS logP -2.4 ALOGPS logP -1.9 ChemAxon logS 0.7 ALOGPS pKa (Strongest Acidic) 11.3 ChemAxon pKa (Strongest Basic) -3.6 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 90.15 Ų ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 34.38 m³·mol⁻¹ ChemAxon Polarizability 15.26 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 degradation PW000826 inner membrane transport PW000786
KEGG Pathways:	Fructose and mannose metabolism ec00051
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-1900000000-73abedcfedce730de924 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-014j-1900000000-5f2bd8fc908e0f2d17d8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4s-9000000000-4ae8072a5651434f44b4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-3900000000-e7a20de995c932bdb5d1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-03dj-6900000000-03f10dd2373a0985cc0e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-1ef6b887ff1a4477de1f View in MoNA MS Mass Spectrum (Electron Ionization) Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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)
Links
External Links:	Resource Link CHEBI ID 16055 HMDB ID HMDB00849 Pubchem Compound ID 840 Kegg ID C02476 ChemSpider ID 23642 Wikipedia Rhamnose BioCyc ID RHAMNOSE EcoCyc ID RHAMNOSE Ligand Expo RAM

Enzymes

Transporters