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Showing Compound Sialyllacto-N-neotetraose c (FDB023990)

Record Information
Version1.0
Creation date2011-09-21 00:38:08 UTC
Update date2015-07-21 06:57:57 UTC
Primary IDFDB023990
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSialyllacto-N-neotetraose c
DescriptionSialyllacto-N-neotetraose c is an oligosaccharide found in human breast milk. Two additional sialylated pentasaccharides include sialyllacto-N-tetraose-a and -b. Oligosaccharides containing N-acetyl (or N-glycolyl) neuraminic acid, i.e. sialylated oligosaccharides, are important components of glycoproteins and glycolipids. In nature, sialylated oligosaccharides often occur as homologous series, with incremental differences in composition, and as structural isomers with subtle differences in monosaccharide sequence and glycosyl linkage and, possibly, with presence or absence of molecular branching. A large number of such sialylated oligosaccharides occur in human milk, where they may have important biological functions. Major structural isomers of these acidic oligosaccharides in human milk are 3'- and 6'-sialyllactoses and the sialyllacto-N-tetraoses; appreciable amounts of 3'- and 6'-sialyllactosamines are found in human urine. (PMID:11471815) Oligosaccharides in human milk inhibit enteric pathogens in vitro and in vivo. Neutral milk oligosaccharides vary among individuals and over the course of lactation. (PMID:10683228) [HMDB]
CAS Number64003-55-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility62.6 g/LALOGPS
logP-3.2ALOGPS
logP-12ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count29ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area510.09 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity205.96 m³·mol⁻¹ChemAxon
Polarizability94.04 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC37H62N2O29
IUPAC name(2R,4S,5R,6R)-2-{[(3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
InChI IdentifierInChI=1S/C37H62N2O29/c1-10(45)38-19-12(47)3-37(36(59)60,68-31(19)22(52)14(49)5-41)61-9-18-23(53)26(56)27(57)34(64-18)66-30-17(8-44)63-33(20(25(30)55)39-11(2)46)67-32-24(54)16(7-43)62-35(28(32)58)65-29(15(50)6-42)21(51)13(48)4-40/h4,12-35,41-44,47-58H,3,5-9H2,1-2H3,(H,38,45)(H,39,46)(H,59,60)/t12-,13-,14+,15+,16+,17+,18?,19+,20+,21+,22+,23-,24-,25+,26-,27+,28+,29+,30+,31+,32-,33-,34-,35-,37+/m0/s1
InChI KeySXMGGNXBTZBGLU-IBUUTZGMSA-N
Isomeric SMILESCC(=O)N[C@@H]1[C@@H](O)[C@H](O[C@@H]2OC(CO[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](O)[C@H](O)[C@H]2O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]1O
Average Molecular Weight998.8842
Monoisotopic Molecular Weight998.343824032
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
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Beta-hydroxy aldehyde
  • Fatty acyl
  • Pyran
  • Oxane
  • Acetamide
  • Alpha-hydroxyaldehyde
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Primary alcohol
  • Aldehyde
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Alcohol
  • 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, Positivesplash10-01q9-0400040009-67dd67eda04977a96ef82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01sl-4903063104-47887538c3880ad579802017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-8932240003-1701bae6c829e036f2932017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0203-4629130007-71827ae78e1094ab35e52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-9622220306-e8aa42cc4ca2146a9e892017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvi-9734300000-609eb0e286083d90a1d12017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006t-7100000029-db42f49a9e486a61b3472021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-4160401089-b290fe1b6dbca676e1322021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000001-0d871c83b17a07c8a8482021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0j59-0200011059-ff65ac79c275960b2f4f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-7504051019-75718b8a0efe28b75c462021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi0-6925030000-d935d2f834b8fc5521092021-09-23View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53477861
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06593
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
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference