Raffinose (CHEM012546)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:57:44 UTC
Update Date2016-11-09 01:14:36 UTC
Accession NumberCHEM012546
Identification
Common NameRaffinose
ClassSmall Molecule
DescriptionA trisaccharide composed of alpha-D-galactopyranose, alpha-D-glucopyranose and beta-D-fructofuranose joined in sequence by 1->6 and 12 glycosidic linkages, respectively.
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
6g-alpha-D-GalactosylsucroseChEBI
alpha-D-Galactopyranosyl-(1->6)-alpha-D-glucopyranosyl beta-D-fructofuranosideChEBI
alpha-D-Galp-(1->6)-alpha-D-GLCP-(12)-beta-D-frufChEBI
GossyposeChEBI
MelitoseChEBI
MelitrioseChEBI
RafinoseChEBI
RaflinoseChEBI
6g-a-D-GalactosylsucroseGenerator
6g-Α-D-galactosylsucroseGenerator
a-D-Galactopyranosyl-(1->6)-a-D-glucopyranosyl b-D-fructofuranosideGenerator
Α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl β-D-fructofuranosideGenerator
a-D-Galp-(1->6)-a-D-GLCP-(12)-b-D-frufGenerator
Α-D-galp-(1->6)-α-D-GLCP-(12)-β-D-frufGenerator
D-(+)-RaffinoseHMDB
D-RaffinoseHMDB
beta-D-Fructofuranosyl O-alpha-D-galactopyranosyl-(1→6)-alpha-D-glucopyranosideHMDB
Β-D-fructofuranosyl O-α-D-galactopyranosyl-(1→6)-α-D-glucopyranosideHMDB
RaffinoseHMDB
Chemical FormulaC18H32O16
Average Molecular Mass504.437 g/mol
Monoisotopic Mass504.169 g/mol
CAS Registry Number512-69-6
IUPAC Name(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol
Traditional Nameraffinose
SMILESOC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C18H32O16/c19-1-5-8(22)11(25)13(27)16(31-5)30-3-7-9(23)12(26)14(28)17(32-7)34-18(4-21)15(29)10(24)6(2-20)33-18/h5-17,19-29H,1-4H2/t5-,6-,7-,8+,9-,10-,11+,12+,13-,14-,15+,16+,17-,18+/m1/s1
InChI KeyMUPFEKGTMRGPLJ-ZQSKZDJDSA-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 Solubility669 g/LALOGPS
logP-3.4ALOGPS
logP-6.3ChemAxon
logS0.12ALOGPS
pKa (Strongest Acidic)11.7ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area268.68 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity101.19 m³·mol⁻¹ChemAxon
Polarizability46.17 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0i00-0984100000-9982c277f436fd7788a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0a4o-0909000000-8e525d469d91c8d958cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-004l-0229100000-0e86b420bc16a12fcb5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-06vi-1529000000-ca7b5ce31b75cedc69b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-0076-9430100000-a53bd43a032e7db1cb4dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 40V, negativesplash10-00fr-0986000000-0bdcdaf84ed0bc932795Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, negativesplash10-0uk9-7930060000-ac8500ed18415634b666Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0kp0-9820010000-016241d403acb7b8c491Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-004i-0090000000-b2481c83084387e12838Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 12V, negativesplash10-0udi-0100090000-6da14a924bf87e052d40Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 19V, negativesplash10-0fb9-2910030000-27a02c65bb1897d0b234Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 25V, negativesplash10-002r-6910000000-a9a928caa280abfbd94dSpectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 30V, negativesplash10-000i-9710000000-49017cc7d06a2393eab3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-0udi-0000090000-2f07c4e073c08b44cbc6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, negativesplash10-0udi-0200090000-48ca69a647f8a160cfcfSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 25V, negativesplash10-0udi-2611090000-02d0b16ed861ce2e2251Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-0ug0-4910020000-75edd90b36765151b923Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, negativesplash10-0079-9820000000-163d92c370b7f8085dc9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 45V, negativesplash10-0kmr-9510000000-b6c552ccce26ade9d72cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 55V, negativesplash10-05g0-9300000000-7eeb9c4ff5f74d594a40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0901000000-0da93ae66a255c539613Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gi-0905000000-b14ef3fbf37ecca83a6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9800000000-07dcde9d0cb5481f432bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2901000000-f86191b929c7806ddd56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-0900000000-e4a2b4341d424cbea7d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-6910000000-5d77ce1936f86d2012feSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C 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
1D NMR1H 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 IDHMDB0003213
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001145
BiGG IDNot Available
BioCyc IDCPD-1099
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRaffinose
Chemspider ID388379
ChEBI ID16634
PubChem Compound ID439242
Kegg Compound IDC00492
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23317449
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23879777
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23882273
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24001862
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24354450
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24360500
7. Toussaint M, Latger-Cannard V, Caron A, Lecompte T, Vigneron C, Menu P: Hemoglobin-based oxygen carriers do not alter platelet functions: study of three chemically modified hemoglobin solutions. Intensive Care Med. 2003 Jan;29(1):62-8. Epub 2002 Nov 30.
8. Gross KC, Houghton MP, Senterfit LB: Presumptive speciation of Streptococcus bovis and other group D streptococci from human sources by using arginine and pyruvate tests. J Clin Microbiol. 1975 Jan;1(1):54-60.
9. Xue S, Paterson W, Valdez D, Miller D, Christoff B, Wong LT, Diamant NE: Effect of an o-raffinose cross-linked haemoglobin product on oesophageal and lower oesophageal sphincter motor function. Neurogastroenterol Motil. 1999 Dec;11(6):421-30.
10. Persson AE, Schnermann J, Agerup B, Eriksson NE: The hydraulic conductivity of the rat proximal tubular wall determined with colloidal solutions. Pflugers Arch. 1975 Oct 16;360(1):25-44.
11. Lobley RW, Burrows PC, Warwick R, Dawson DJ, Holmes R: Simultaneous assessment of intestinal permeability and lactose tolerance with orally administered raffinose, lactose and L-arabinose. Clin Sci (Lond). 1990 Aug;79(2):175-83.
12. Rodrigues Silva C, Dutra de Oliveira JE, de Souza RA, Silva HC: Effect of a rice bran fiber diet on serum glucose levels of diabetic patients in Brazil. Arch Latinoam Nutr. 2005 Mar;55(1):23-7.
13. Hessels J, Snoeyink EJ, Platenkamp AJ, Voortman G, Steggink J, Eidhof HH: Assessment of intestinal permeability: enzymatic determination of urinary mannitol, raffinose, sucrose and lactose on Hitachi analyzer. Clin Chem Lab Med. 2003 Jan;41(1):33-8.
14. Horodniceanu T, Delbos F: [Group D streptococci in human infections: identification and sensitivity to antibiotics (author's transl)]. Ann Microbiol (Paris). 1980 Sep-Oct;131B(2):131-44.
15. Lieberthal W, Fuhro R, Alam H, Rhee P, Szebeni J, Hechtman HB, Favuzza J, Veech RL, Valeri CR: Comparison of the effects of a 50% exchange-transfusion with albumin, hetastarch, and modified hemoglobin solutions. Shock. 2002 Jan;17(1):61-9.
16. Gundermann KJ, Lie TS: Problems of competition in charcoal hemoperfusion for the treatment of intoxications. Artif Organs. 1979 Nov;3(4):346-9.