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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-03-03 11:33:16 UTC
Update Date2019-07-23 05:56:22 UTC
HMDB IDHMDB0011740
Secondary Accession Numbers
  • HMDB11740
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
Data?1563861382
Synonyms
ValueSource
3-O-alpha-D-Glucopyranosyl-D-fructoseChEBI
alpha-D-GLCP-(1->3)-D-fruChEBI
D-(+)-TuranoseChEBI
D-TuranoseChEBI
3-O-a-D-Glucopyranosyl-D-fructoseGenerator
3-O-α-D-glucopyranosyl-D-fructoseGenerator
a-D-GLCP-(1->3)-D-fruGenerator
α-D-GLCP-(1->3)-D-fruGenerator
3-O-Hexopyranosylhex-2-uloseHMDB
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
DescriptionThis compound belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. These are compounds composed of a mono- or disaccharide moiety 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 of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty alcohol
  • Beta-hydroxy ketone
  • Oxane
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Alcohol
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity69.98 m³·mol⁻¹ChemAxon
Polarizability31.33 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 8 TMS)splash10-0uxr-0892000000-e8ab17454ea3418a8d75JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 8 TMS)splash10-1000-1892000000-56f7efd87990218227e8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0941000000-7f32f8dee830f3f6bcbdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxs-0941000000-7205b28e43abbbe9c824JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03k9-9558000000-ff59077c1fe357edc2cfJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-07w9-6501239000-ce62c87dc5f53187c36fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-002v-4869000000-85a1e952e9ed60ffc211JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004s-9702000000-2ab0e4671f636f3381c1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002s-9300000000-a9c970dbec22a064e622JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03gl-1908000000-61eefa62dae8fd8a80d7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-6901000000-8d8d2739984c831239baJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9700000000-9751d050646634523820JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0036-7794000000-8e533bd6a826e2e2fb71JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-7922000000-f95a7becdb85adefd933JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07g0-9800000000-2c0a51d0022f26da8707JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002107
KNApSAcK IDNot Available
Chemspider ID4574343
KEGG Compound IDC19636
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTuranose
METLIN IDNot Available
PubChem Compound5460935
PDB IDOTU
ChEBI ID32528
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.