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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:25 UTC
HMDB IDHMDB00849
Secondary Accession NumbersNone
Metabolite Identification
Common NameRhamnose
DescriptionRhamnose (Rham) is a naturally occurring deoxy sugar. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Rhamnose occurs in nature in its L-form as L-rhamnose (6-deoxy-L-mannose). This is unusual, since most of the naturally occurring sugars are in D-form. Rhamnose is commonly bound to other sugars in nature. It is a common glycone component of glycosides from many plants. Rhamnose is also a component of the outer cell membrane of certain bacteria. L-rhamnose is metabolized to L-Lactaldehyde, which is a branching point in the metabolic pathway of L-fucose and L-rhamnose utilization. It exists in two anomeric forms, alpha-L-rhamnose and beta-L-rhamnose.
Structure
Thumb
Synonyms
ValueSource
6-Deoxy-L-mannoseChEBI
L-(+)-RhamnoseChEBI
L-MannomethyloseChEBI
L-RhaChEBI
L-RhamnoseChEBI
6-Deoxy-L(+)-mannoseHMDB
6-Deoxy-L-mannopyranoseHMDB
6-Deoxy-mannoseHMDB
6-DeoxyhexopyranoseHMDB
6-DeoxyhexoseHMDB
6-DeoxymannoseHMDB
IsodulcitHMDB
IsodulcitolHMDB
L(+)-RhamnoseHMDB
L(+)-Rhamnose monohydrateHMDB
L-(+)-Rhamnose 1-hydrateHMDB
L-(+)-Rhamnose hydrate = 6-deoxy-L-mannose monohydrateHMDB
L-(+)-Rhamnose monohydrateHMDB
L-RhamnopyranoseHMDB
L-Rhamnose for biochemistryHMDB
L-Rhamnose monohydrateHMDB
LocaoseHMDB
mono(6-Deoxy-b-L-mannopyranosyl) esterHMDB
mono(6-Deoxy-beta-L-mannopyranosyl) esterHMDB
P-(6-Deoxy-b-L-mannopyranosyl) esterHMDB
P-(6-Deoxy-beta-L-mannopyranosyl) esterHMDB
RhamnopyranoseHMDB
RhamnosemonohydrateHMDB
UDP-RhamnoseHMDB
Uridine 5-pyrophosphateHMDB
Uridine diphosphate rhamnoseHMDB
Chemical FormulaC6H12O5
Average Molecular Weight164.1565
Monoisotopic Molecular Weight164.068473494
IUPAC Name(3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol
Traditional NameL-(+)-rhamnose
CAS Registry Number3615-41-6
SMILES
C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O
InChI Identifier
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
InChI KeyInChIKey=SHZGCJCMOBCMKK-JFNONXLTSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point122 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility827.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.38 m3·mol-1ChemAxon
Polarizability15.09 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0019-9600000000-8cb337afbc2d297157bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0uy0-9600000000-cb7dbb4d86a5bc544704View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9200000000-89022407246ea7a22497View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-2196b54a850c456b7ee8View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Feces
Tissue Location
  • Platelet
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01869
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001176
KNApSAcK IDNot Available
Chemspider ID23642
KEGG Compound IDC00507
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRhamnose
NuGOwiki LinkHMDB00849
Metagene LinkHMDB00849
METLIN ID5812
PubChem Compound25310
PDB ID1CB8
ChEBI ID62346
References
Synthesis ReferenceCambronero 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)
General References
  1. Citron DM, Baron EJ, Finegold SM, Goldstein EJ: Short prereduced anaerobically sterilized (PRAS) biochemical scheme for identification of clinical isolates of bile-resistant Bacteroides species. J Clin Microbiol. 1990 Oct;28(10):2220-3. [2229345 ]
  2. Ohri SK, Somasundaram S, Koak Y, Macpherson A, Keogh BE, Taylor KM, Menzies IS, Bjarnason I: The effect of intestinal hypoperfusion on intestinal absorption and permeability during cardiopulmonary bypass. Gastroenterology. 1994 Feb;106(2):318-23. [8299899 ]
  3. Miki K, Butler R, Moore D, Davidson G: Rapid and simultaneous quantification of rhamnose, mannitol, and lactulose in urine by HPLC for estimating intestinal permeability in pediatric practice. Clin Chem. 1996 Jan;42(1):71-5. [8565237 ]
  4. Nomura R, Nakano K, Ooshima T: Molecular analysis of the genes involved in the biosynthesis of serotype specific polysaccharide in the novel serotype k strains of Streptococcus mutans. Oral Microbiol Immunol. 2005 Oct;20(5):303-9. [16101966 ]
  5. Frirdich E, Whitfield C: Lipopolysaccharide inner core oligosaccharide structure and outer membrane stability in human pathogens belonging to the Enterobacteriaceae. J Endotoxin Res. 2005;11(3):133-44. [15949142 ]
  6. Ohse M, Matsuo M, Ishida A, Kuhara T: Screening and diagnosis of beta-ureidopropionase deficiency by gas chromatographic/mass spectrometric analysis of urine. J Mass Spectrom. 2002 Sep;37(9):954-62. [12271438 ]
  7. Albers MJ, Steyerberg EW, Hazebroek FW, Mourik M, Borsboom GJ, Rietveld T, Huijmans JG, Tibboel D: Glutamine supplementation of parenteral nutrition does not improve intestinal permeability, nitrogen balance, or outcome in newborns and infants undergoing digestive-tract surgery: results from a double-blind, randomized, controlled trial. Ann Surg. 2005 Apr;241(4):599-606. [15798461 ]
  8. Van Kuilenburg AB, Van Lenthe H, Assmann B, Gohlich-Ratmann G, Hoffmann GF, Brautigam C, Wevers RA, Van Gennip AH: Detection of beta-ureidopropionase deficiency with HPLC-electrospray tandem mass spectrometry and confirmation of the defect at the enzyme level. J Inherit Metab Dis. 2001 Dec;24(7):725-32. [11804209 ]
  9. Anderson AD, Poon P, Greenway GM, MacFie J: A simple method for the analysis of urinary sucralose for use in tests of intestinal permeability. Ann Clin Biochem. 2005 May;42(Pt 3):224-6. [15949159 ]
  10. Whaley DN, Wiggs LS, Miller PH, Srivastava PU, Miller JM: Use of Presumpto Plates to identify anaerobic bacteria. J Clin Microbiol. 1995 May;33(5):1196-202. [7615728 ]
  11. Chia JS, Lin YL, Lien HT, Chen JY: Platelet aggregation induced by serotype polysaccharides from Streptococcus mutans. Infect Immun. 2004 May;72(5):2605-17. [15102769 ]
  12. Hosono M, Sugawara S, Ogawa Y, Kohno T, Takayanagi M, Nitta K: Purification, characterization, cDNA cloning, and expression of asialofetuin-binding C-type lectin from eggs of shishamo smelt (Osmerus [Spirinchus] lanceolatus). Biochim Biophys Acta. 2005 Sep 15;1725(2):160-73. [16112459 ]
  13. Bjarnason I, Smethurst P, Macpherson A, Walker F, McElnay JC, Passmore AP, Menzies IS: Glucose and citrate reduce the permeability changes caused by indomethacin in humans. Gastroenterology. 1992 May;102(5):1546-50. [1568563 ]