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Record Information
Version1.0
Created at2006-05-22 15:12:41 UTC
Updated at2020-09-10 21:50:14 UTC
NP-MRD IDNP0000023
Secondary Accession NumbersNone
Natural Product Identification
Common NameRaffinose
DescriptionRaffinose, also known as gossypose or melitose, 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. Raffinose is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, raffinose participates in a number of enzymatic reactions. In particular, raffinose and D-galactose can be biosynthesized from stachyose through its interaction with the enzyme Alpha-galactosidase a. In addition, raffinose can be converted into sucrose and D-galactose; which is catalyzed by the enzyme Alpha-galactosidase a. In humans, raffinose is involved in galactose metabolism. A trisaccharide composed of alpha-D-galactopyranose, alpha-D-glucopyranose and beta-D-fructofuranose joined in sequence by 1->6 and 12 glycosidic linkages, respectively.
Structure
Thumb
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 Weight504.4371
Monoisotopic Molecular Weight504.169034976
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
CAS Registry Number512-69-6
SMILES
[H][C@]1(CO)O[C@@](CO)(O[C@@]2([H])O[C@]([H])(CO[C@@]3([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]3([H])O)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@@]([H])(O)[C@]1([H])O
InChI Identifier
InChI=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
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR13C NMR SpectrumJSpectraViewer
Species of Origin
SpeciesAnimalia
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point80 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility203 mg/mLNot Available
LogPNot AvailableNot 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
User Submitted Data
Not Available
HMDB IDHMDB0003213
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001145
Chemspider IDNot Available
KEGG Compound IDC00492
BioCyc IDCPD-1099
BiGG IDNot Available
Wikipedia LinkRaffinose
METLIN IDNot Available
PubChem Compound439242
PDB IDNot Available
ChEBI ID16634
References
General References
  1. 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. [PubMed:16187674 ]
  2. 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. [PubMed:2167807 ]
  3. 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. [PubMed:1176592 ]
  4. 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. [PubMed:12528024 ]
  5. 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. [PubMed:10583849 ]
  6. 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. [PubMed:1237863 ]
  7. 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. [PubMed:12636047 ]
  8. 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. [PubMed:7458116 ]
  9. 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. [PubMed:11795671 ]
  10. Gundermann KJ, Lie TS: Problems of competition in charcoal hemoperfusion for the treatment of intoxications. Artif Organs. 1979 Nov;3(4):346-9. [PubMed:533425 ]
  11. Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]