Disialyllactose (CHEM034749)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:11:01 UTC
Update Date2016-11-09 01:21:11 UTC
Accession NumberCHEM034749
Identification
Common NameDisialyllactose
ClassSmall Molecule
DescriptionDisialyllactose belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. Disialyllactose is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass924.806 g/mol
Monoisotopic Mass924.307 g/mol
CAS Registry Number18409-15-9
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
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 IdentifierInChI=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
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 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0cel-0828015098-b2d713e51be84bbf8263Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mo-0209003000-1ce09f03167f95ceab80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-6938001000-df20adf0314406572cbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0abc-2923810044-d28ff343a24de5edba71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a70-8549110001-d97c4fa07291d27d2520Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3559000000-43c7b65e0c738d84bc62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05di-1311051209-8ba4b8dda3057cd245b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03l1-0491412612-76931820494134177702Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00pi-9870313140-5d37d73734c32dc83273Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-8090100084-7f9ba834399e650bd8ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3090000020-6930c6437640788f5ca7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9462010020-9d07f528035ec4ad7db1Spectrum
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
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 IDHMDB0006692
FooDB IDFDB021805
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID10174971
ChEBI IDNot Available
PubChem Compound ID12002504
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579
2. Stahl, 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
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.