Disialyllacto-N-tetraose (CED0012595)

Record Information
Version1.0
Creation Date2016-05-26 07:16:39 UTC
Update Date2026-04-06 11:02:52 UTC
Accession NumberCHEM036161
Identification
Common NameDisialyllacto-N-tetraose
ClassSmall Molecule
Description
Disialyllacto-N-tetraose belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. It has the chemical formula C48H79N3O37. With an average molecular weight of 1,290 g/mol, Disialyllacto-N-tetraose is a heavy molecule.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Di-N-acetylneuraminosyllacto-N-tetraoseHMDB
NeuAc-alpha-(2-3)-gal-beta-(1-3)-neuac-alpha-(2-6)-glcnac-beta-(1-3)-gal-beta-(1-4)-GLCMeSH, HMDB
(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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}-3-hydroxy-5-[(1-hydroxyethylidene)amino]oxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateGenerator, HMDB
Disialyllacto-N-tetraoseMeSH
Chemical FormulaC48H79N3O37
Average Molecular Mass1290.139 g/mol
Monoisotopic Mass1289.439 g/mol
CAS Registry Number61278-38-4
IUPAC Name(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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}-5-acetamido-3-hydroxyoxan-2-yl]methoxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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}-5-acetamido-3-hydroxyoxan-2-yl]methoxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
SMILES[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]1O[C@@H](O[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)[C@@H]2O)[C@H](NC(C)=O)[C@@H](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](O)CO)C(O)=O)[C@H]2O)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO
InChI IdentifierInChI=1S/C48H79N3O37/c1-12(57)49-23-15(60)4-47(45(74)75,86-37(23)26(64)17(62)6-52)78-11-22-30(68)36(25(51-14(3)59)42(82-22)85-39-28(66)19(8-54)80-43(33(39)71)83-35-21(10-56)79-41(73)32(70)31(35)69)84-44-34(72)40(29(67)20(9-55)81-44)88-48(46(76)77)5-16(61)24(50-13(2)58)38(87-48)27(65)18(63)7-53/h15-44,52-56,60-73H,4-11H2,1-3H3,(H,49,57)(H,50,58)(H,51,59)(H,74,75)(H,76,77)/t15-,16-,17+,18+,19+,20+,21+,22+,23+,24+,25+,26+,27+,28-,29-,30+,31+,32+,33+,34+,35+,36+,37+,38+,39-,40-,41?,42-,43-,44-,47+,48-/m0/s1
InChI KeyFCIROHDMPFOSFG-LAVSNGQLSA-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
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • Glycosyl compound
  • C-glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Dicarboxylic acid or derivatives
  • Pyran
  • Oxane
  • Acetamide
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • 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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility153 g/LALOGPS
logP-2.6ALOGPS
logP-13ChemAxon
logS-0.93ALOGPS
pKa (Strongest Acidic)2.56ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count37ChemAxon
Hydrogen Donor Count24ChemAxon
Polar Surface Area647.8 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity264.81 m³·mol⁻¹ChemAxon
Polarizability122.48 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0089-0390000022-de52b83b24d5fb17bf50Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0411000329-71f0bb6caa39dc80046eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01q9-3930001024-7b1e18284674410df5c6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dl-1591000000-ba1c5e527f93670ae0efNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0adi-7986000000-1bcbcecd9d3e813563ecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-6944300000-8019a244394b9a7c757dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fef-0190000012-e768ae8bf3bcdbe3e831Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-008a-1490000001-5d5e6d76513bf1ee03ffNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6y-4590100010-eaca24f90f5ac9a8c252Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0079-5290000000-d72945ba4045145cee51Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-2491000000-684fd54cef257ed58769Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052g-9440000002-1a3c191b9187d65744a0Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity ValuesNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureE-selectinP98105Rattus norvegicusPredicted (SEA)0.0778492
Sialic acid-binding Ig-like lectin 7 structureClick to view 3D structureSialic acid-binding Ig-like lectin 7Q9Y286HumansPredicted (SEA)0.155698
Click to view 3D structureMyelin-associated glycoproteinP20916HumansPredicted (SEA)0.233548
CD44 antigen structureClick to view 3D structureCD44 antigenP16070HumansPredicted (SEA)0.155698
CD44 antigen structureClick to view 3D structureCD44 antigenP15379Mus musculusPredicted (SEA)0.155698
B-cell receptor CD22 structureClick to view 3D structureB-cell receptor CD22P20273HumansPredicted (SEA)0.233548
Click to view 3D structureB-cell receptor CD22P35329Mus musculusPredicted (SEA)0.467095
Click to view 3D structureN-acetyllactosaminide alpha-1,3-galactosyltransferaseP50127Sus scrofaPredicted (SEA)1.55698
Endo-beta-N-acetylglucosaminidase structureClick to view 3D structureEndo-beta-N-acetylglucosaminidaseQ9ZB22Arthrobacter protophormiaePredicted (SEA)1.01204
Click to view 3D structureNeuraminidaseB4URF0Influenza A virusPredicted (SEA)8.87481
Click to view 3D structureAlpha-amylaseQ7M328Sus scrofa domesticusPredicted (SEA)0.856341
Neuraminidase structureClick to view 3D structureNeuraminidaseQ3S340Influenza B virusPredicted (SEA)0.778492
Click to view 3D structureKiller cell lectin-like receptor subfamily B member 1AP27471Rattus norvegicusPredicted (SEA)1.01204
Neurotrophic factor BDNF precursor form structureClick to view 3D structureNeurotrophic factor BDNF precursor formP23560HumansPredicted (SEA)0.700643
Pleiotrophin structureClick to view 3D structurePleiotrophinP21246HumansPredicted (SEA)0.700643
Click to view 3D structureNeuraminidaseA5Z252Influenza A virusPredicted (SEA)7.16213
Click to view 3D structureNeuraminidaseP03471Influenza A virus (A/Memphis/1/1971(H3N2))Predicted (SEA)6.15009
Click to view 3D structureSialidase-3Q9UQ49HumansPredicted (SEA)2.95827
Bone morphogenetic protein 6 structureClick to view 3D structureBone morphogenetic protein 6P22004HumansPredicted (SEA)1.63483
Platelet factor 4 structureClick to view 3D structurePlatelet factor 4P02776HumansPredicted (SEA)1.63483
Myelin-associated glycoprotein structureClick to view 3D structureMyelin-associated glycoproteinP20917Mus musculusPredicted (SEA)1.16774
Galectin-3 structureClick to view 3D structureGalectin-3P17931HumansPredicted (SEA)17.5939
Click to view 3D structureHemagglutinin-neuraminidaseQ06992Human parainfluenza virus 1Predicted (SEA)1.40129
Neuraminidase structureClick to view 3D structureNeuraminidaseP03468Influenza A virus (A/Puerto Rico/8/1934(H1N1))Predicted (SEA)13.3901
Neuraminidase structureClick to view 3D structureNeuraminidaseQ194T1Influenza A virusPredicted (SEA)3.11397
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0006594
FooDB IDFDB023991
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID2342164
ChEBI ID89907
PubChem Compound ID3085216
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Shen Z, Warren CD, Newburg DS: High-performance capillary electrophoresis of sialylated oligosaccharides of human milk. Anal Biochem. 2000 Mar 1;279(1):37-45.
2. Lemonnier M, Fournet B, Bourrillon R: [Isolation and chemical characterization of a new sialyloligosaccharide in the urine of pregnant women]. C R Acad Sci Hebd Seances Acad Sci D. 1975 Jun 16;280(23):2705-7.
3. Koseki M, Tsurumi K: The isolation and characterization of a new sialic acid-containing oligosaccharide from human colostrum. Fukushima J Med Sci. 1969 May;15(3):79-83.
4. Lemonnier M, Bourrillon R: Characterization and structure of a sialic acid-containing hexasaccharide isolated from human pregnancy urine. Carbohydr Res. 1976 Oct;51(1):99-106.
5. Sabharwal H, Nilsson B, Gronberg G, Chester MA, Dakour J, Sjoblad S, Lundblad A: Oligosaccharides from feces of preterm infants fed on breast milk. Arch Biochem Biophys. 1988 Sep;265(2):390-406.