Record Information
Version1.0
Creation date2010-04-08 22:10:06 UTC
Update date2019-11-26 03:06:34 UTC
Primary IDFDB012320
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameStachyose
DescriptionIsolated from soybean meal (Glycine max), tubers of Japanese artichoke (Stachys tubifera) and lentils Stachyose is a tetrasaccharide consisting of two D-galactose units, one D-glucose unit, and one D-fructose unit sequentially linked. Stachyose is a normal human metabolite present in human milk and is naturally found in many vegetables (e.g. green beans, soybeans and other beans) and plants. The glycosylation of serum transferrin from galactosemic patients with a deficiency of galactose-1-phosphate uridyl transferase (EC 2. 7.7 12) is abnormal but becomes normal after treatment with a galactose-free diet. Adhering to a galactose-free diet by strictly avoiding dairy products and known hidden sources of galactose does not completely normalize galactose-1-phosphate (gal-1-P) in erythrocytes from patients with galactosemia, since galactose released from stachyose may be absorbed and contribute to elevated gal-1-P values in erythrocytes of galactosemic patients. (PMID: 7671975, 9499382); Stachyose is a tetrasaccharide consisting of two ?-D-galactose units, one ?-D-glucose unit, and one ?-D-fructose unit sequentially linked as gal(?1?6)gal(?1?6)glc(?1?2?)fru. Stachyose is naturally found in numerous vegetables (e.g. green beans, soybeans and other beans) and plants.
CAS Number470-55-3
Structure
Thumb
Synonyms
SynonymSource
a-D-Galp-(1->6)-a-D-galp-(1->6)-a-D-glcp-(12)-b-D-frufGenerator
alpha-D-Galp-(1->6)-alpha-D-galp-(1->6)-alpha-D-glcp-(12)-beta-D-frufChEBI
b-D-Fructofuranosyl O-a-D-galactopyranosyl-(1->6)-O-a-D-galactopyranosyl-(1->6)-a-D-glucopyranoside, 9CI, 8CIdb_source
b-Galactandb_source
beta-D-Fructofuranosyl O-alpha-D-galactopyranosyl-(1->6)-O-alpha-D-galactopyranosyl-(1->6)-alpha-D-glucopyranosideHMDB
Cicerosedb_source
D-stachyosebiospider
Lupeosedb_source
Manneotetrosedb_source
O-a-D-Galactopyranosyl-(1->6)O-a-D-galactopyranosyl-(1->6)O-a-D-galactopyranosyl-b-D-fructofuranosideGenerator
O-alpha-D-Galactopyranosyl-(1->6)O-alpha-D-galactopyranosyl-(1->6)O-alpha-D-galactopyranosyl-beta-D-fructofuranosideChEBI
O-α-D-galactopyranosyl-(1->6)O-α-D-galactopyranosyl-(1->6)O-α-D-galactopyranosyl-β-D-fructofuranosideGenerator
α-D-galp-(1->6)-α-D-galp-(1->6)-α-D-glcp-(12)-β-D-frufGenerator
Predicted Properties
PropertyValueSource
Water Solubility411 g/LALOGPS
logP-2.9ALOGPS
logP-8.1ChemAxon
logS-0.21ALOGPS
pKa (Strongest Acidic)11.63ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area347.83 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity133.6 m³·mol⁻¹ChemAxon
Polarizability62.55 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC24H42O21
IUPAC name2-({6-[(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3,4,5-trihydroxyoxan-2-yl}methoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
InChI IdentifierInChI=1S/C24H42O21/c25-1-6-10(28)14(32)17(35)21(41-6)39-3-8-11(29)15(33)18(36)22(42-8)40-4-9-12(30)16(34)19(37)23(43-9)45-24(5-27)20(38)13(31)7(2-26)44-24/h6-23,25-38H,1-5H2
InChI KeyUQZIYBXSHAGNOE-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(CO)(OC2OC(COC3OC(COC4OC(CO)C(O)C(O)C4O)C(O)C(O)C3O)C(O)C(O)C2O)C(O)C1O
Average Molecular Weight666.5777
Monoisotopic Molecular Weight666.221858406
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 43.25%; H 6.35%; O 50.40%DFC
Melting PointMp 167-170° (anhyd.)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D +131.3 (c, 4.5 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-9051231e83f301a09a0eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ei-0902300000-1d2431079f0fcf16f362Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9800000000-9f5834420ffbcf1d03e5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900001000-1b21dc3904103d99d080Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1900000000-92c5416ad039dfd6ec6bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-6911000000-f2c6489ad24930392c3eSpectrum
NMRNot Available
ChemSpider ID388624
ChEMBL IDCHEMBL1625803
KEGG Compound IDC01613
Pubchem Compound ID439531
Pubchem Substance IDNot Available
ChEBI ID17164
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03553
CRC / DFC (Dictionary of Food Compounds) IDHGH56-Q:HGH56-Q
EAFUS IDNot Available
Dr. Duke IDSTACHYOSE
BIGG IDNot Available
KNApSAcK IDC00001150
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDStachyose
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.