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Showing Compound Disialyllacto-N-tetraose (FDB023991)

Record Information
Version1.0
Creation date2011-09-21 00:38:09 UTC
Update date2015-07-21 06:57:58 UTC
Primary IDFDB023991
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDisialyllacto-N-tetraose
DescriptionDisialyllacto-N-tetraose is a sialyl hexasaccharide from human milk, which has also been isolated from the urine of pregnant women and has also been found in the feces of preterm human newborns. Its structure is that of lacto-N-tetraose with one of the residues of sialic acid linked alpha-(2->3) to the terminal nonreducing residue of D-galactose and the other sialic acid residue linked alpha-(2->6) to the N-acetyl-D-glucosamine residue. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. (PMID:10683228, 809156, 5363606, 1000529, 3421714) [HMDB]
CAS Number61278-38-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
Chemical FormulaC48H79N3O37
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
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
Isomeric 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
Average Molecular Weight1290.1388
Monoisotopic Molecular Weight1289.439240557
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
  • 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
Ontology
Disposition

Biological location:

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, Positivesplash10-0089-0390000022-de52b83b24d5fb17bf502017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0411000329-71f0bb6caa39dc80046e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-3930001024-7b1e18284674410df5c62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-1591000000-ba1c5e527f93670ae0ef2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-7986000000-1bcbcecd9d3e813563ec2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-6944300000-8019a244394b9a7c757d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fef-0190000012-e768ae8bf3bcdbe3e8312021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-008a-1490000001-5d5e6d76513bf1ee03ff2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6y-4590100010-eaca24f90f5ac9a8c2522021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-5290000000-d72945ba4045145cee512021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-2491000000-684fd54cef257ed587692021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9440000002-1a3c191b9187d65744a02021-09-25View Spectrum
NMRNot Available
ChemSpider ID2342164
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID3085216
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06594
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