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Showing Compound Disialyllactose (FDB021805)

Record Information
Version1.0
Creation date2011-04-11 16:28:51 UTC
Update date2019-11-26 03:20:53 UTC
Primary IDFDB021805
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number18409-15-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC34H56N2O27
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
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
Isomeric 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
Average Molecular Weight924.8056
Monoisotopic Molecular Weight924.307044596
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0cel-0828015098-b2d713e51be84bbf82632017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mo-0209003000-1ce09f03167f95ceab802017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-6938001000-df20adf0314406572cbf2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0abc-2923810044-d28ff343a24de5edba712017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a70-8549110001-d97c4fa07291d27d25202017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3559000000-43c7b65e0c738d84bc622017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05di-1311051209-8ba4b8dda3057cd245b82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03l1-0491412612-769318204941341777022021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00pi-9870313140-5d37d73734c32dc832732021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-8090100084-7f9ba834399e650bd8eb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3090000020-6930c6437640788f5ca72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9462010020-9d07f528035ec4ad7db12021-09-22View Spectrum
NMRNot Available
ChemSpider ID10174971
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID12002504
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06692
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference