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Showing Compound Raffinose (FDB000661)

Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2019-11-26 02:55:10 UTC
Primary IDFDB000661
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRaffinose
DescriptionOccurs in cotton seeds, sugar beet and manna. Widely distributed in plants, especies in the seeds. Sweet taste. Sweetness 0.48 x sucrose 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 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 can be hydrolyzed to D-galactose and sucrose by the enzyme ?-galactosidase (?-GAL), an enzyme not found in the human digestive tract. ?-GAL also hydrolyzes other ?-galactosides such as stachyose, verbascose, and galactinol, if present. The enzyme does not cleave ?-linked galactose, as in lactose.; 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; Trisaccharide; A trisaccharide occurring in Australian manna (from Eucalyptus spp, Myrtaceae) and in cottonseed meal. -- Pubchem.
CAS Number512-69-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
b-D-Fructofuranosyl O-b-D-glucopyranosyl-(1->6)-a-D-glucopyranoside, 9ci, 8ciHMDB
b-D-Glucopyranosyl-(1->6)-a-D-glucopyranosyl-(1->2)-b-D-fructofuranosideHMDB
beta-D-GLCP-(1->6)-alpha-D-GLCP-(12)-beta-D-frufHMDB
6G-alpha-D-galactosylsucrosebiospider
6G-alpha-delta-galactosylsucrosebiospider
b-D-Fructofuranosyl a-D-galactopyranosyl-(1->6)-a-D-glucopyranoside, 9CIdb_source
D-(+)-raffinosebiospider
D-raffinosebiospider
Delta-(+)-raffinosebiospider
Delta-raffinosebiospider
Gossyposedb_source
Melitosedb_source
Melitriosedb_source
Raffinose (8CI)biospider
Raffinose hydratebiospider
Raffinose, purebiospider
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
Polarizability47 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H32O16
IUPAC name2-[(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
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
InChI KeyMUPFEKGTMRGPLJ-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(CO)(OC2OC(COC3OC(CO)C(O)C(O)C3O)C(O)C(O)C2O)C(O)C1O
Average Molecular Weight504.4371
Monoisotopic Molecular Weight504.169034976
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 42.86%; H 6.39%; O 50.75%DFC
Melting PointMp 118° (anhyd.)DFC
Boiling PointNot Available
Experimental Water Solubility203 mg/mLYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +123 (c, 2 in H2O) (anhyd.)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSRaffinose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-5312900000-8c1da6b96f865046dbc2Spectrum
Predicted GC-MSRaffinose, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001j-4901027000-c14285b3dedf9a545038Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0901000000-16626312db2eecdabfad2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gi-0905000000-addfdf153c257344d0362015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9800000000-7c8dcd3c627e5d3ba25d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0901000000-16626312db2eecdabfad2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gi-0905000000-addfdf153c257344d0362015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9800000000-7c8dcd3c627e5d3ba25d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2901000000-0bb4fa33c7a31ca7c1652015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-1900000000-cde6726b02a16b9fff3c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-6910000000-9efcfdce81511949fe062015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2901000000-0bb4fa33c7a31ca7c1652015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-1900000000-cde6726b02a16b9fff3c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-6910000000-9efcfdce81511949fe062015-04-25View Spectrum
NMRNot Available
ChemSpider ID10102
ChEMBL IDCHEMBL175500
KEGG Compound IDC00492
Pubchem Compound ID10542
Pubchem Substance IDNot Available
ChEBI ID16634
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03213
CRC / DFC (Dictionary of Food Compounds) IDBFL28-I:BFL28-I
EAFUS IDNot Available
Dr. Duke IDRAFFINOSE
BIGG IDNot Available
KNApSAcK IDC00001145
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDRaffinose
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
flatugenicDUKE
Enzymes
NameGene NameUniProt ID
Alpha-galactosidase AGLAP06280
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043 map00052
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.