Neokestose (CHEM023547)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:08:06 UTC
Update Date2016-11-09 01:17:44 UTC
Accession NumberCHEM023547
Identification
Common NameNeokestose
ClassSmall Molecule
DescriptionNeokestose is found in cereals and cereal products. Neokestose is isolated from aqueous alcoholic extracts of oat stalks
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6g-KestotrioseHMDB
b-D-Fructofuranosyl 6-O-b-D-fructofuranosyl-a-D-glucopyranoside, 8ciHMDB
neo-KestoseHMDB
O-b-D-Fructofuranosyl-(2->6)-a-D-glucopyranosyl b-D-fructofuranosideHMDB
NeokestoseMeSH
Chemical FormulaC18H32O16
Average Molecular Mass504.437 g/mol
Monoisotopic Mass504.169 g/mol
CAS Registry Number3688-75-3
IUPAC Name2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol
Traditional Name2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol
SMILESOCC1OC(CO)(OCC2OC(OC3(CO)OC(CO)C(O)C3O)C(O)C(O)C2O)C(O)C1O
InChI IdentifierInChI=1S/C18H32O16/c19-1-6-10(24)14(28)17(4-21,32-6)30-3-8-9(23)12(26)13(27)16(31-8)34-18(5-22)15(29)11(25)7(2-20)33-18/h6-16,19-29H,1-5H2
InChI KeyHQFMTRMPFIZQJF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility611 g/LALOGPS
logP-3.2ALOGPS
logP-6.1ChemAxon
logS0.08ALOGPS
pKa (Strongest Acidic)11.65ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area268.68 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity101.62 m³·mol⁻¹ChemAxon
Polarizability46.44 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00du-4201900000-deed11d2b97ce51998ccSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0f89-7611139000-d53b3243b6b1666d1f82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06wc-1809230000-eca26a3dc669aaeb0cbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0904000000-5f5e638316fc7fcc5c6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-4900000000-f26a50985cfbbeb08a0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-3902210000-83278e7e02f26eac69afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0901100000-86325e4bb5e6abe028c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-6901000000-1be15e2cf46766b1e373Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2405590000-eb8c9ff127f4cb767f21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9103700000-43bc77d5d771e0e674a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056u-9401000000-fd80e69238ae56ec256cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0101890000-ffc271795a3a997a6dbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ts-7906430000-5c6f1f1128b2471ebb94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002k-9733100000-b7cf3f7fb9eda3d4e9e5Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0029921
FooDB IDFDB001178
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID92512
ChEBI ID175865
PubChem Compound ID102436
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Alvaro-Benito M, Sainz-Polo MA, Gonzalez-Perez D, Gonzalez B, Plou FJ, Fernandez-Lobato M, Sanz-Aparicio J: Structural and kinetic insights reveal that the amino acid pair Gln-228/Asn-254 modulates the transfructosylating specificity of Schwanniomyces occidentalis beta-fructofuranosidase, an enzyme that produces prebiotics. J Biol Chem. 2012 Jun 1;287(23):19674-86. doi: 10.1074/jbc.M112.355503. Epub 2012 Apr 16.
2. Bekers M, Upite D, Kaminska E, Laukevics J, Ionina R, Vigants A: Catalytic activity of zymomonas mobilis extracellular "levan-levansucrase" complex in sucrose medium. Commun Agric Appl Biol Sci. 2003;68(2 Pt A):321-4.
3. Der Agopian RG, Purgatto E, Cordenunsi BR, Lajolo FM: Synthesis of fructooligosaccharides in banana 'prata' and its relation to invertase activity and sucrose accumulation. J Agric Food Chem. 2009 Nov 25;57(22):10765-71. doi: 10.1021/jf902163f.
4. Flieger M, Kantorova M, Halada P, Kuzma M, Pazoutova S, Stodulkova E, Kolinska R: Oligosaccharides produced by submerged cultures of Claviceps africana and Claviceps sorghi. Folia Microbiol (Praha). 2005;50(3):198-204.
5. Linde D, Rodriguez-Colinas B, Estevez M, Poveda A, Plou FJ, Fernandez Lobato M: Analysis of neofructooligosaccharides production mediated by the extracellular beta-fructofuranosidase from Xanthophyllomyces dendrorhous. Bioresour Technol. 2012 Apr;109:123-30. doi: 10.1016/j.biortech.2012.01.023. Epub 2012 Jan 14.
6. Atiyeh H, Duvnjak Z: Study of the production of fructose and ethanol from sucrose media by Saccharomyces cerevisiae. Appl Microbiol Biotechnol. 2001 Oct;57(3):407-11.
7. Okada H, Fukushi E, Yamamori A, Kawazoe N, Onodera S, Kawabata J, Shiomi N: Novel fructopyranose oligosaccharides isolated from fermented beverage of plant extract. Carbohydr Res. 2010 Feb 11;345(3):414-8. doi: 10.1016/j.carres.2009.12.003. Epub 2009 Dec 11.
8. Ueno K, Onodera S, Kawakami A, Yoshida M, Shiomi N: Molecular characterization and expression of a cDNA encoding fructan:fructan 6G-fructosyltransferase from asparagus (Asparagus officinalis). New Phytol. 2005 Mar;165(3):813-24.
9. Matulova M, Husarova S, Capek P, Sancelme M, Delort AM: NMR structural study of fructans produced by Bacillus sp. 3B6, bacterium isolated in cloud water. Carbohydr Res. 2011 Mar 1;346(4):501-7. doi: 10.1016/j.carres.2010.12.012. Epub 2010 Dec 21.
10. Polo A, Linde D, Estevez M, Fernandez-Lobato M, Sanz-Aparicio J: Crystallization and preliminary X-ray diffraction analysis of the fructofuranosidase from Xanthophyllomyces dendrorhous. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2010 Nov 1;66(Pt 11):1441-4. doi: 10.1107/S1744309110029192. Epub 2010 Oct 28.
11. Havey MJ, Galmarini CR, Gokce AF, Henson C: QTL affecting soluble carbohydrate concentrations in stored onion bulbs and their association with flavor and health-enhancing attributes. Genome. 2004 Jun;47(3):463-8.
12. Liu F, Liu Y, Meng Y, Yang M, He K: Structure of polysaccharide from Polygonatum cyrtonema Hua and the antiherpetic activity of its hydrolyzed fragments. Antiviral Res. 2004 Sep;63(3):183-9.
13. Lasseur B, Lothier J, Djoumad A, De Coninck B, Smeekens S, Van Laere A, Morvan-Bertrand A, Van den Ende W, Prud'homme MP: Molecular and functional characterization of a cDNA encoding fructan:fructan 6G-fructosyltransferase (6G-FFT)/fructan:fructan 1-fructosyltransferase (1-FFT) from perennial ryegrass (Lolium perenne L.). J Exp Bot. 2006;57(11):2719-34. Epub 2006 Jul 13.
14. Katapodis P, Kalogeris E, Kekos D, Macris BJ, Christakopoulos P: Biosynthesis of fructo-oligosaccharides by Sporotrichum thermophile during submerged batch cultivation in high sucrose media. Appl Microbiol Biotechnol. 2004 Jan;63(4):378-82. Epub 2003 Jun 12.
15. Ueno K, Ishiguro Y, Yoshida M, Onodera S, Shiomi N: Cloning and functional characterization of a fructan 1-exohydrolase (1-FEH) in edible burdock (Arctium lappa L.). Chem Cent J. 2011 Apr 5;5(1):16. doi: 10.1186/1752-153X-5-16.
16. Linde D, Macias I, Fernandez-Arrojo L, Plou FJ, Jimenez A, Fernandez-Lobato M: Molecular and biochemical characterization of a beta-fructofuranosidase from Xanthophyllomyces dendrorhous. Appl Environ Microbiol. 2009 Feb;75(4):1065-73. doi: 10.1128/AEM.02061-08. Epub 2008 Dec 16.
17. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.