Human Metabolome Database Version 3.5

Showing metabocard for Turanose (HMDB11740)

Record Information
Version 3.5
Creation Date 2009-03-03 04:33:16 -0700
Update Date 2013-02-08 17:27:16 -0700
Secondary Accession Numbers None
Metabolite Identification
Common Name Turanose
Description D-(+)-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
  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 Formula C12H22O11
Average Molecular Weight 342.2965
Monoisotopic Molecular Weight 342.116211546
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 IUPAC Name turanose
CAS Registry Number 547-25-1
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
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Disaccharides
Sub Class Dihexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • glycosylfructose(ChEBI)
  • 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 Parent Dihexoses
Status Detected and Quantified
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 168 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1000 mg/mL at 25 °C Not Available
LogP -4.80 MEYLAN,WM & HOWARD,PH (1995)
Predicted Properties
Property Value Source
Water Solubility 298 g/L ALOGPS
LogP -2.76 ALOGPS
LogP -5 ChemAxon
LogS -0.06 ALOGPS
pKa (strongest acidic) 12.1 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 11 ChemAxon
Hydrogen Donor Count 8 ChemAxon
Polar Surface Area 197.37 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 69.98 ChemAxon
Polarizability 31.33 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.5 (0.0-1.0) uM Adult (>18 years old) Both Comment Prostate Cancer
Associated Disorders and Diseases
Disease References
Prostate cancer
  • 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 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB002107
      KNApSAcK ID Not Available
      Chemspider ID 4574343 Link_out
      KEGG Compound ID C19636 Link_out
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Turanose Link_out
      NuGOwiki Link HMDB11740 Link_out
      Metagene Link HMDB11740 Link_out
      METLIN ID Not Available
      PubChem Compound 5460935 Link_out
      PDB ID OTU Link_out
      ChEBI ID 32528 Link_out
      Synthesis Reference Not Available
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References Not Available