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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-30 11:00:13 UTC
Update Date2021-09-14 15:39:07 UTC
HMDB IDHMDB0006692
Secondary Accession Numbers
  • HMDB06692
Metabolite Identification
Common NameDisialyllactose
DescriptionDisialyllactose is a naturally occurring oligosaccharide present in the cell surface and in breast milk. Disialyllactose has been identified as one of the binding sites of the C fragment of the clostridial tetanus toxin, binding with great specificity and high affinity. Clostridial neurotoxins, botulinum and tetanus, gain entry into motor neurons by binding to the sialic or N-acetylneuraminic acid (NeuAc) residues of gangliosides and specific protein receptors attached to the cell's surface. Neurotoxins interact with motor neurons, blocking acetylcholine release and causing muscle paralysis and death. The glycosidic linkage between Neu5Ac and other monosaccharides is susceptible to hydrolysis at low pH, and disialyl lactose is unstable under acidic conditions. (PMID: 16713287 , 16104015 , 7263800 , 7972078 ).
Structure
Data?1582752399
Synonyms
ValueSource
a-Neu5ac-(2->8)-a-neu5ac-(2->3)-b-D-gal-(1->4)-D-GLCHMDB
alpha-Neu5ac-(2->8)-alpha-neu5ac-(2->3)-beta-D-gal-(1->4)-D-GLCHMDB
Di-(N-acetylneuramin)lactoseHMDB
O-(N-Acetyl-a-neuraminosyl)-(2->8)-O-(N-acetyl-a-neuraminosyl)-(2->3)-O-b-D-galactopyranosyl-(1->4)-D-glucopyranoseHMDB
O-(N-Acetyl-a-neuraminyl)-(2->8)-O-(N-acetyl-a-neuraminyl)-(2->3)-O-b-D-galactopyranosyl-(1->4)-D-glucopyranoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2-8)-O-(N-acetyl-alpha-neuraminosyl)-(2-3)-O-beta-D-galactopyranosyl-(1-4)- D-glucopyranoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2-8)-O-(N-acetyl-alpha-neuraminosyl)-(2-3)-O-beta-delta-galactopyranosyl-(1-4)- D-glucopyranoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->8)-O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucopyranoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->8)-O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)- D-glucopyranoseHMDB
O-(N-Acetyl-alpha-neuraminyl)-(2-8)-O-(N-acetyl-alpha-neuraminyl)-(2-3)-O-beta-D-galactopyranosyl-(1-4)-D-glucopyranoseHMDB
O-(N-Acetyl-alpha-neuraminyl)-(2-8)-O-(N-acetyl-alpha-neuraminyl)-(2-3)-O-beta-delta-galactopyranosyl-(1-4)-delta-glucopyranoseHMDB
O-(N-Acetyl-alpha-neuraminyl)-(2->8)-O-(N-acetyl-alpha-neuraminyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucopyranoseHMDB
O-(N-Acetyl-alpha-neuraminyl)-(2->8)-O-(N-acetyl-alpha-neuraminyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)-delta- glucopyranoseHMDB
Sia-(2-8)-sia-(2-3)gal-(1-4)GLCHMDB
(2S,4S,5R,6R)-2-{[(1S,2R)-1-[(2R,3R,4S,6S)-6-carboxy-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]-1,3-dihydroxypropan-2-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateGenerator, HMDB
Disialyl lactoseMeSH, HMDB
AlphaNeu5ac(2,8)alphaneu5ac(2,3)betadgal(1,4)DGLCMeSH, HMDB
Chemical FormulaC34H56N2O27
Average Molecular Weight924.8056
Monoisotopic Molecular Weight924.307044596
IUPAC Name(2S,4S,5R,6R)-6-[(1S,2R)-2-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid
Traditional Name(2S,4S,5R,6R)-6-[(1S,2R)-2-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid
CAS Registry Number18409-15-9
SMILES
[H][C@]1(O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O3)[C@H](O)[C@@H](CO)O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O3)[C@H](O)[C@H](O)CO)C(O)=O)C(O)=O)[C@H]2O)[C@H](O)[C@@H](O)C(O)O[C@@H]1CO
InChI Identifier
InChI=1S/C34H56N2O27/c1-9(41)35-17-11(43)3-33(31(53)54,61-26(17)19(46)13(45)5-37)60-15(7-39)21(48)27-18(36-10(2)42)12(44)4-34(62-27,32(55)56)63-28-20(47)14(6-38)58-30(24(28)51)59-25-16(8-40)57-29(52)23(50)22(25)49/h11-30,37-40,43-52H,3-8H2,1-2H3,(H,35,41)(H,36,42)(H,53,54)(H,55,56)/t11-,12-,13+,14+,15+,16+,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27+,28-,29?,30-,33+,34-/m0/s1
InChI KeyIESOVNOGVZBLMG-MTEFBGAJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acylneuraminic acids
Alternative Parents
Substituents
  • Oligosaccharide
  • N-acylneuraminic acid
  • Neuraminic acid
  • C-glucuronide
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Dicarboxylic acid or derivatives
  • Pyran
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Carbonyl group
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility104 g/LALOGPS
logP-2.5ALOGPS
logP-9.5ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)2.45ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count27ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area480.63 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity188.88 m³·mol⁻¹ChemAxon
Polarizability86.15 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+267.71130932474
DeepCCS[M-H]-265.98730932474
DeepCCS[M-2H]-300.39730932474
DeepCCS[M+Na]+273.94730932474
AllCCS[M+H]+271.232859911
AllCCS[M+H-H2O]+271.732859911
AllCCS[M+NH4]+270.732859911
AllCCS[M+Na]+270.532859911
AllCCS[M-H]-287.532859911
AllCCS[M+Na-2H]-291.632859911
AllCCS[M+HCOO]-296.332859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialyllactose 10V, Positive-QTOFsplash10-0cel-0828015098-b2d713e51be84bbf82632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialyllactose 20V, Positive-QTOFsplash10-00mo-0209003000-1ce09f03167f95ceab802017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialyllactose 40V, Positive-QTOFsplash10-03dl-6938001000-df20adf0314406572cbf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialyllactose 10V, Negative-QTOFsplash10-0abc-2923810044-d28ff343a24de5edba712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialyllactose 20V, Negative-QTOFsplash10-0a70-8549110001-d97c4fa07291d27d25202017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialyllactose 40V, Negative-QTOFsplash10-0a4i-3559000000-43c7b65e0c738d84bc622017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialyllactose 10V, Positive-QTOFsplash10-05di-1311051209-8ba4b8dda3057cd245b82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialyllactose 20V, Positive-QTOFsplash10-03l1-0491412612-769318204941341777022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialyllactose 40V, Positive-QTOFsplash10-00pi-9870313140-5d37d73734c32dc832732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialyllactose 10V, Negative-QTOFsplash10-00di-8090100084-7f9ba834399e650bd8eb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialyllactose 20V, Negative-QTOFsplash10-001i-3090000020-6930c6437640788f5ca72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialyllactose 40V, Negative-QTOFsplash10-0006-9462010020-9d07f528035ec4ad7db12021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021805
KNApSAcK IDNot Available
Chemspider ID10174971
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12002504
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceStahl, Bernd; Boehm, Guenther; Finke, Berndt; Georgi, Gilda; Jelinek, Juergen; Schmitt, Joachim J. Oligosaccharide mixture. Ger. Offen. (2001), 6 pp. CODEN: GWXXBX DE 19958985 A1 20010613 CAN 135:18816 AN 2001:431764
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. von Nicolai H, Esser P, Lauer E: Partial purification and properties of neuraminidase from Bifidobacterium lactentis. Hoppe Seylers Z Physiol Chem. 1981 Feb;362(2):153-62. [PubMed:7216169 ]
  2. Conway MC, Whittal RM, Baldwin MA, Burlingame AL, Balhorn R: Electrospray mass spectrometry of NeuAc oligomers associated with the C fragment of the tetanus toxin. J Am Soc Mass Spectrom. 2006 Jul;17(7):967-76. Epub 2006 May 19. [PubMed:16713287 ]
  3. Jayaraman S, Eswaramoorthy S, Kumaran D, Swaminathan S: Common binding site for disialyllactose and tri-peptide in C-fragment of tetanus neurotoxin. Proteins. 2005 Nov 1;61(2):288-95. [PubMed:16104015 ]
  4. Veh RW, Michalski JC, Corfield AP, Sander-Wewer M, Gies D, Schauer R: New chromatographic system for the rapid analysis and preparation of colostrum sialyloligosaccharides. J Chromatogr. 1981 Aug 7;212(3):313-22. [PubMed:7263800 ]
  5. Cho JW, Troy FA 2nd: Polysialic acid engineering: synthesis of polysialylated neoglycosphingolipids by using the polysialyltransferase from neuroinvasive Escherichia coli K1. Proc Natl Acad Sci U S A. 1994 Nov 22;91(24):11427-31. [PubMed:7972078 ]