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Record Information
Version3.6
Creation Date2006-05-22 15:12:41 UTC
Update Date2016-02-11 01:06:07 UTC
HMDB IDHMDB03213
Secondary Accession NumbersNone
Metabolite Identification
Common NameRaffinose
DescriptionTrisaccharide. A trisaccharide occurring in Australian manna (from Eucalyptus spp, Myrtaceae) and in cottonseed meal. -- Pubchem; Raffinose is a complex carbohydrate, a trisaccharide composed of galactose, fructose, and glucose. It can be found in beans, cabbage, brussels sprouts, broccoli, asparagus, other vegetables, and whole grains. Raffinose is hydrolysed to D-galactose and sucrose by D-galactosidase (D-GAL) (1). D-GAL also hydrolyses other D-galactosides such as stachyose, verbascose, and galactinol [1-O-(D-galactosyl)-myoinositol], if present. The enzyme does not cleave linked galactose, as in lactose. -- Wikipedia; Raffinose is also known as melitose and may be thought of as galactose + sucrose connected via an alpha(1-6) glycosidic linkage and so raffinose can be broken apart into galactose and sucrose via the enzyme alpha-galactosidase. Human intestines do not contain this enzyme. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
6g-alpha-D-GalactosylsucroseHMDB
6g-alpha-delta-GalactosylsucroseHMDB
D-(+)-RaffinoseHMDB
D-RaffinoseHMDB
delta-(+)-RaffinoseHMDB
delta-RaffinoseHMDB
GossyposeHMDB
MelitoseHMDB
MelitrioseHMDB
Raffinose hydrateHMDB
Chemical FormulaC18H32O16
Average Molecular Weight504.4371
Monoisotopic Molecular Weight504.169034976
IUPAC Name(3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol
Traditional Name(3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol
CAS Registry Number512-69-6
SMILES
OC[C@H]1O[C@@](CO)(OC2O[C@H](COC3O[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 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 KeyInChIKey=MUPFEKGTMRGPLJ-BQCSWRFHSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassOligosaccharides
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • C-glycosyl compound
  • Oxane
  • Oxolane
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility669.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity101.19 m3·mol-1ChemAxon
Polarizability46.73 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Platelet
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043map00052
GalactosemiaSMP00182Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.8 +/- 5.4 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000661
KNApSAcK IDC00001145
Chemspider ID10102
KEGG Compound IDC00492
BioCyc IDCPD-169
BiGG IDNot Available
Wikipedia LinkRaffinose
NuGOwiki LinkHMDB03213
Metagene LinkHMDB03213
METLIN ID138
PubChem Compound10542
PDB IDNot Available
ChEBI ID397485
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [533425 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GLA
Uniprot ID:
P06280
Molecular weight:
Not Available
Reactions
Raffinose + Water → Beta-D-Galactose + Sucrosedetails
Stachyose + Water → Raffinose + Beta-D-Galactosedetails