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Record Information
Creation Date2009-03-03 11:33:16 UTC
Update Date2016-02-11 01:22:10 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameTuranose
DescriptionD-(+)-Turanose is a reducing disaccharide. Its systematic name is a-D-glucopyranosyl-(1-->3)-a-D-fructofuranose. It is an analog of sucrose not metabolized by higher plants, but rather acquired through the action of sucrose transporters for intracellular carbohydrate signaling. In addition to its involvement in signal transduction, D-(+)-Turanose can also be used as a carbon source by many organisms including numerous species of bacteria and fungi (Wikipedia).
  1. 3-O-a-D-Glucopyranosyl-D-Fructose
  2. 3-O-alpha-D-Glucopyranosyl-D-Fructose
  3. 3-O-Hexopyranosylhex-2-ulose
  4. D-(+)-Turanose (van)
  5. D-Turanose
  6. Turanose (van)
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
IUPAC Name(3S,4R,5R)-1,4,5,6-tetrahydroxy-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexan-2-one
Traditional Nameturanose
CAS Registry Number547-25-1
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty acyl glycosides. These are compounds containing fatty acyl chain linked to a carbohydrate moiety through a glycosidic bond. Fatty acyl glycosides are composed of a glycosyl moiety (one or several units) linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides
Alternative Parents
  • Fatty acyl glycoside
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Fatty alcohol
  • Oxane
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
Experimental Properties
Melting Point168 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 25 °CNot Available
LogP-4.80MEYLAN,WM & HOWARD,PH (1995)
Predicted Properties
Water Solubility298.0 mg/mLALOGPS
pKa (Strongest Acidic)12.1ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area197.37 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity69.98 m3·mol-1ChemAxon
Polarizability31.33 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 8 TMS)splash10-3yzb000000-e8ab17454ea3418a8d75View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 8 TMS)splash10-4yzb000000-56f7efd87990218227e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-fvqz000000-85a1e952e9ed60ffc211View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-zs38000000-2ab0e4671f636f3381c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-zd20000000-a9c970dbec22a064e622View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate Cancer
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002107
KNApSAcK IDNot Available
Chemspider ID4574343
KEGG Compound IDC19636
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTuranose
NuGOwiki LinkHMDB11740
Metagene LinkHMDB11740
METLIN IDNot Available
PubChem Compound5460935
ChEBI ID32528
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available