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Record Information
Version2.0
Created at2006-08-12 23:36:48 UTC
Updated at2021-08-19 23:58:13 UTC
NP-MRD IDNP0000568
Secondary Accession NumbersNone
Natural Product Identification
Common NameStachyose
DescriptionStachyose 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 ).
Structure
Thumb
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 Mass666.5777 Da
Monoisotopic Mass666.22186 Da
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
CAS Registry Number470-55-3
SMILES
OC[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 Identifier
InChI=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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium ampeloprasumFooDB
Allium sativumFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arachis hypogaeaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bryum capillareLOTUS Database
Bubalus bubalisFooDB
Canavalia ensiformisLOTUS Database
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Coffea arabica L.FooDB
ColumbaFooDB
ColumbidaeFooDB
Corylus avellanaFooDB
Daphnia pulexLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Ervum lens-
Fraxinus ornusKNApSAcK Database
Gallus gallusFooDB
Glycine maxKNApSAcK Database
Gossypium hirsutumLOTUS Database
Helianthus annuus L.FooDB
Jasminum officinaleKNApSAcK Database
Lagopus mutaFooDB
Lantana camaraKNApSAcK Database
Lens culinarisFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lonicera caeruleaLOTUS Database
Lupinus luteusKNApSAcK Database
Lupinus mutabilisLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
Mentha arvensisFooDB
Nelumbo nuciferaFooDB
Nicotiana tabacumLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
Olea europaeaLOTUS Database
Origanum vulgareFooDB
OryctolagusFooDB
Ovis ariesFooDB
Phaseolus coccineusLOTUS Database
Phaseolus vulgarisLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Pisum sativumFooDB
Plantago asiaticaKNApSAcK Database
Prunus dulcisFooDB
Rehmannia glutinosaKNApSAcK Database
Salacia oblongaLOTUS Database
Soja max-
Solanum tuberosumFooDB
Stachys spp.KNApSAcK Database
Stachys tubiferKNApSAcK Database
Stachys tubiferaKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Theobroma cacaoFooDB
Trigonella foenum-graecumFooDB
Triticum aestivumFooDB
Verbena officinalisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna unguiculataLOTUS Database
Vigna unguiculata ssp. unguiculataFooDB
Vitis vinifera L.FooDB
Xerosicyos danguyiLOTUS Database
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
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 PointNot AvailableNot Available
Boiling Point1044.20 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-2.880 (est)The Good Scents Company Information System
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0003553
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012320
KNApSAcK IDC00001150
Chemspider ID388624
KEGG Compound IDC01613
BioCyc IDCPD-170
BiGG IDNot Available
Wikipedia LinkStachyose
METLIN ID6951
PubChem Compound439531
PDB IDNot Available
ChEBI ID17164
Good Scents IDrw1698711
References
General References
  1. 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. [PubMed:7504304 ]
  2. 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. [PubMed:7671975 ]
  3. Hoch G, Peterbauer T, Richter A: Purification and characterization of stachyose synthase from lentil (Lens culinaris) seeds: galactopinitol and stachyose synthesis. Arch Biochem Biophys. 1999 Jun 1;366(1):75-81. doi: 10.1006/abbi.1999.1212. [PubMed:10334866 ]
  4. (). 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. .