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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-24 16:20:02 UTC
Update Date2020-02-26 21:26:34 UTC
HMDB IDHMDB0006593
Secondary Accession Numbers
  • HMDB06593
Metabolite Identification
Common 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 ).
Structure
Data?1582752394
Synonyms
ValueSource
LS-Tetrasaccharide cHMDB
LSTCHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-delta-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)-delta-glucoseHMDB
SLNT-cHMDB
(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}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateGenerator
Chemical FormulaC37H62N2O29
Average Molecular Weight998.8842
Monoisotopic Molecular Weight998.343824032
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
Traditional 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
CAS Registry Number64003-55-0
SMILES
CC(=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
InChI Identifier
InChI=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
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
  • 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0400040009-67dd67eda04977a96ef8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01sl-4903063104-47887538c3880ad57980Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-8932240003-1701bae6c829e036f293Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0203-4629130007-71827ae78e1094ab35e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-9622220306-e8aa42cc4ca2146a9e89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvi-9734300000-609eb0e286083d90a1d1Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Breast Milk
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified170.7015256 +/- 7.5634623 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023990
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477861
PDB IDNot Available
ChEBI ID89905
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceMurakami, Tatsuya; Suzawa, Toshiyuki; Yamazaki, Motoo; Sato, Mitsuo; Endo, Tetsuo; Koizumi, Satoshi; Imada, Teruyoshi. Screening of compounds with specific site affinity, probes for the process, and use of oligosaccharides for drug delivery, diagnostic agents, and pharmaceuticals. Jpn. Kokai Tokkyo Koho (2004), 25 pp. CODEN: JKXXAF JP 2004138397 A 20040513 CAN 140:386061 AN 2004:391539
Material Safety Data Sheet (MSDS)Not 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. [PubMed:10683228 ]
  2. Shen Z, Warren CD, Newburg DS: Resolution of structural isomers of sialylated oligosaccharides by capillary electrophoresis. J Chromatogr A. 2001 Jul 6;921(2):315-21. [PubMed:11471815 ]