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Record Information
Version3.6
Creation Date2009-03-03 11:33:16 UTC
Update Date2013-02-09 00:27:16 UTC
HMDB IDHMDB11740
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).
Structure
Thumb
Synonyms
  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
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)CO
InChI Identifier
InChI=1S/C12H22O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4,6-16,18-21H,1-3H2/t4-,6-,7-,8-,9+,10-,11-,12-/m1/s1
InChI KeyRULSWEULPANCDV-PIXUTMIVSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassDisaccharides
Sub ClassDihexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • glycosylfructose(ChEBI)
Substituents
  • 1,2 Diol
  • Acetal
  • Alpha Ketoaldehyde
  • Beta Ketoaldehyde
  • Fatty Acyl Glycoside
  • Fatty Alcohol
  • Glycosyl Compound
  • Ketone
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentDihexoses
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
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
PropertyValueSource
Water Solubility298.0ALOGPS
logP-2.8ALOGPS
logP-5ChemAxon
logS-0.06ALOGPS
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
Spectra
SpectraGC-MSMS/MS
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate Cancer
details
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. Pubmed: 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
PDB IDOTU
ChEBI ID32528
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available