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Record Information
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-01-11 19:15:12 UTC
Secondary Accession Numbers
  • HMDB00849
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.
L(+)-Rhamnose monohydrateHMDB
L-(+)-Rhamnose 1-hydrateHMDB
L-(+)-Rhamnose hydrate = 6-deoxy-L-mannose monohydrateHMDB
L-(+)-Rhamnose monohydrateHMDB
L-Rhamnose for biochemistryHMDB
L-Rhamnose monohydrateHMDB
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
Uridine 5-pyrophosphateHMDB
Uridine diphosphate rhamnoseHMDB
Rhamnose, L isomerMeSH
Rhamnose, L-isomerMeSH
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
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors

Route of exposure:


Biological location:

Physical Properties
Experimental Properties
Melting Point122 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility827 g/LALOGPS
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
Polarizability15.09 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-ff79aee2e9ac3a4f53c8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-23d1bd654495aefbf615View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-ff79aee2e9ac3a4f53c8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-23d1bd654495aefbf615View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-9500000000-cfa9e0d8f1f20b29e5d8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-002r-9346400000-7524daf3b04caf0c441aView in MoNA
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-2196b54a850c456b7ee8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-5daf054ff3eb9127d3caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-f7729c93b964e01cb774View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-9000000000-2c46a67befe14c31d7a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-86321b083a11f93bb55bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-5900000000-2accd457fe7b58b9b032View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-9e349c8fad042f6a3e99View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
Tissue Locations
  • Platelet
Normal Concentrations
FecesDetected but not Quantified Infant (0-1 year old)Both
FecesDetected but not Quantified Adult (>18 years old)Both
Abnormal Concentrations
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001176
KNApSAcK IDNot Available
Chemspider ID23642
KEGG Compound IDC00507
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRhamnose
PubChem Compound25310
ChEBI ID62346
Synthesis ReferenceSanchez Miguel Cambronero, Ruiz Pedro Antonio Garcia. Process for obtaining L-rhamnose of high purity from rhamnoglucosides. 1997, Patent ES2103205A1 (
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:1568563 ]