.alpha.-D-Glucopyranoside, .beta.-D-fructofuranosyl O-.alpha.-D-galactopyranosyl-( 1.fwdarw.6)-O-.alpha.-D-g alactopyranosyl-(1.fwdarw.6)- (CHEM012440)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:55:46 UTC
Update Date2016-11-09 01:14:34 UTC
Accession NumberCHEM012440
Identification
Common Name.alpha.-D-Glucopyranoside, .beta.-D-fructofuranosyl O-.alpha.-D-galactopyranosyl-( 1.fwdarw.6)-O-.alpha.-D-g alactopyranosyl-(1.fwdarw.6)-
ClassSmall Molecule
DescriptionA tetrasaccharide consisting of sucrose having an alpha-D-galactosyl-(1->6)-alpha-D-galactosyl moiety attached at the 6-position of the glucose.
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
alpha-D-Galp-(1->6)-alpha-D-galp-(1->6)-alpha-D-GLCP-(12)-beta-D-frufChEBI
O-alpha-D-Galactopyranosyl-(1->6)O-alpha-D-galactopyranosyl-(1->6)O-alpha-D-galactopyranosyl-beta-D-fructofuranosideChEBI
a-D-Galp-(1->6)-a-D-galp-(1->6)-a-D-GLCP-(12)-b-D-frufGenerator
Α-D-galp-(1->6)-α-D-galp-(1->6)-α-D-GLCP-(12)-β-D-frufGenerator
O-a-D-Galactopyranosyl-(1->6)O-a-D-galactopyranosyl-(1->6)O-a-D-galactopyranosyl-b-D-fructofuranosideGenerator
O-Α-D-galactopyranosyl-(1->6)O-α-D-galactopyranosyl-(1->6)O-α-D-galactopyranosyl-β-D-fructofuranosideGenerator
beta-D-Fructofuranosyl O-alpha-D-galactopyranosyl-(1->6)-O-alpha-D-galactopyranosyl-(1->6)-alpha-D-glucopyranosideHMDB
D-StachyoseHMDB
Β-D-fructofuranosyl O-α-D-galactopyranosyl-(1→6)-O-α-D-galactopyranosyl-(1→6)-α-D-glucopyranosideHMDB
StachyoseHMDB
Chemical FormulaC24H42O21
Average Molecular Mass666.578 g/mol
Monoisotopic Mass666.222 g/mol
CAS Registry Number470-55-3
IUPAC Name(2S,3R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4S,5R,6R)-6-{[(2S,3S,4S,5R)-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
Traditional Name(2S,3R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4S,5R,6R)-6-{[(2S,3S,4S,5R)-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
SMILESOC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO[C@H]3O[C@H](CO[C@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[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/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/t6-,7-,8-,9-,10+,11+,12-,13-,14+,15+,16+,17-,18-,19-,20+,21+,22+,23-,24+/m1/s1
InChI KeyUQZIYBXSHAGNOE-XNSRJBNMSA-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 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
Polarizability61.61 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9b-5402129000-61642294535e87144940Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_14) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0000009000-d94a236a9a5a6bd5c972Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-017i-1828209000-9199e7c55d37d011eac1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-7912000000-8a80b033b9a4ea01bc8eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00ar-7915000000-788f6809791936fee494Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000009000-e38a72ceefebbe0bb3daSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0040-4915000000-fba1f7d256aa66bf110eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-0101009000-c01c60a83d955171e974Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-9a4d05616e9796aaf3a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ei-0902200000-8724dec2357b4a940fedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-8900000000-8bb4399ade337d2bf2e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900001000-02f4bb852a9d5309ddf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1900000000-0f98c8c4de6b8e4eea1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-5910000000-10e95551d72e06a4af9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02u1-0703129000-d54a2da09fac24cd6697Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lxt-3900012000-690517e60a43f657f5e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052e-9402110000-47e64f8f36cdc20b3a22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02ti-0500329000-3cc0bae4bdfdb007458fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9300155000-4c88b7187013b314fab9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9400010000-76e554af98beaaf0d8f5Spectrum
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
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D 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 IDHMDB0003553
FooDB IDFDB012320
Phenol Explorer IDNot Available
KNApSAcK IDC00001150
BiGG IDNot Available
BioCyc IDCPD-170
METLIN ID6951
PDB IDNot Available
Wikipedia LinkStachyose
Chemspider ID388624
ChEBI ID17164
PubChem Compound ID439531
Kegg Compound IDC01613
YMDB IDNot Available
ECMDB IDECMDB03553
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10334866
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10652123
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11789231
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1255266
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12801075
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16656948
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16658766
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16666190
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16668659
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=18970754
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21421343
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=7524207
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=8479952
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=8528153
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=9629861
16. Sandrin MS, Vaughan HA, Dabkowski PL, McKenzie IF: Anti-pig IgM antibodies in human serum react predominantly with Gal(alpha 1-3)Gal epitopes. Proc Natl Acad Sci U S A. 1993 Dec 1;90(23):11391-5.
17. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
18. Wiesmann UN, Rose-Beutler B, Schluchter R: Leguminosae in the diet: the raffinose-stachyose question. Eur J Pediatr. 1995;154(7 Suppl 2):S93-6.
19. Charlwood J, Clayton P, Keir G, Mian N, Winchester B: Defective galactosylation of serum transferrin in galactosemia. Glycobiology. 1998 Apr;8(4):351-7.
20. Lewis blood groups of breastfeeding women tested serologically and by chromatographic analysis of human milk oligosaccharides. Thurl, S., Henker, J., Siegel, M., Tovar, K., Sawatzki, G. Milchwissenschaft (1998), 53(3), 127-129. Publisher: VV-GmbH Volkswirtschaftlicher Verlag, CODEN: MILCAD ISSN: 0026-3788