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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-28 10:43:19 UTC
Update Date2021-09-14 15:46:21 UTC
HMDB IDHMDB0006631
Secondary Accession Numbers
  • HMDB06631
Metabolite Identification
Common NameSialyllacto-N-tetraose c
DescriptionSialyllacto-N-tetraose c is a sialylated oligosaccharide normally occurring in human breast milk. 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. The acidic oligosaccharides of human milk are predominantly sialyloligosaccharides. Pathogens that bind sialic acid-containing glycans on their host mucosal surfaces may be inhibited by human milk sialyloligosaccharides. Sialyl oligosaccharides of human milk/colostrum are generally believed to be of biological significance, for example providing precursors for biosynthesis of brain. The levels of sialyllacto-N-tetraose are higher on day 3 than on day 1. These results are consistent with the view that during the first 3 d of lactation, the concentration of sialyl oligosaccharides in human colostrum change in accordance with the physiological demands of newborn infants. (PMID: 9426699 , 2318868 ; 10683228, 1778981, 17761135, 17587674).
Structure
Data?1582752398
Synonyms
ValueSource
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-D-galactopyranosyl-(1->3)-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->3)-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)- D-glucoseHMDB
2-({6-[(6-{[3,5-dihydroxy-2-(hydroxymethyl)-6-[(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-(1,2,3-trihydroxypropyl)oxane-2-carboxylateGenerator, HMDB
Chemical FormulaC37H62N2O29
Average Molecular Weight998.8842
Monoisotopic Molecular Weight998.343824032
IUPAC Name2-({6-[(6-{[3,5-dihydroxy-2-(hydroxymethyl)-6-[(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-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
Traditional Name2-({6-[(6-{[3,5-dihydroxy-2-(hydroxymethyl)-6-[(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-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
CAS Registry Number155500-52-0
SMILES
CC(=O)NC1C(O)C(OC2OC(COC3(CC(O)C(NC(C)=O)C(O3)C(O)C(O)CO)C(O)=O)C(O)C(O)C2O)C(CO)OC1OC1C(O)C(CO)OC(OC(C(O)CO)C(O)C(O)C=O)C1O
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)
InChI KeySXMGGNXBTZBGLU-UHFFFAOYSA-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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability92.59 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+281.05630932474
DeepCCS[M-H]-279.19530932474
DeepCCS[M-2H]-313.03530932474
DeepCCS[M+Na]+286.84930932474
AllCCS[M+H]+280.232859911
AllCCS[M+H-H2O]+280.832859911
AllCCS[M+NH4]+279.532859911
AllCCS[M+Na]+279.332859911
AllCCS[M-H]-311.732859911
AllCCS[M+Na-2H]-316.632859911
AllCCS[M+HCOO]-322.032859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyllacto-N-tetraose c 10V, Positive-QTOFsplash10-01q9-0400040009-67dd67eda04977a96ef82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyllacto-N-tetraose c 20V, Positive-QTOFsplash10-01sl-4903063104-47887538c3880ad579802017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyllacto-N-tetraose c 40V, Positive-QTOFsplash10-08gi-8932240003-1701bae6c829e036f2932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyllacto-N-tetraose c 10V, Negative-QTOFsplash10-0203-4629130007-71827ae78e1094ab35e52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyllacto-N-tetraose c 20V, Negative-QTOFsplash10-004r-9622220306-e8aa42cc4ca2146a9e892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyllacto-N-tetraose c 40V, Negative-QTOFsplash10-0bvi-9734300000-609eb0e286083d90a1d12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyllacto-N-tetraose c 10V, Positive-QTOFsplash10-0j59-0200011059-ff65ac79c275960b2f4f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyllacto-N-tetraose c 20V, Positive-QTOFsplash10-03ea-7504051019-75718b8a0efe28b75c462021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyllacto-N-tetraose c 40V, Positive-QTOFsplash10-0fi0-6925030000-d935d2f834b8fc5521092021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyllacto-N-tetraose c 10V, Negative-QTOFsplash10-006t-7100000029-db42f49a9e486a61b3472021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyllacto-N-tetraose c 20V, Negative-QTOFsplash10-056s-4160401089-b290fe1b6dbca676e1322021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyllacto-N-tetraose c 40V, Negative-QTOFsplash10-0a4i-9000000001-0d871c83b17a07c8a8482021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024015
KNApSAcK IDNot Available
Chemspider ID3618994
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4418533
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ravindranath MH, Kelley MC, Jones RC, Amiri AA, Bauer PM, Morton DL: Ratio of IgG:IgM antibodies to sialyl Lewis(x) and GM3 correlates with tumor growth after immunization with melanoma-cell vaccine with different adjuvants in mice. Int J Cancer. 1998 Jan 5;75(1):117-24. [PubMed:9426699 ]
  2. Kitagawa H, Nakada H, Numata Y, Kurosaka A, Fukui S, Funakoshi I, Kawasaki T, Shimada I, Inagaki F, Yamashina I: Occurrence of tetra- and pentasaccharides with the sialyl-Le(a) structure in human milk. J Biol Chem. 1990 Mar 25;265(9):4859-62. [PubMed:2318868 ]
  3. Kunz C, Rudloff S, Hintelmann A, Pohlentz G, Egge H: High-pH anion-exchange chromatography with pulsed amperometric detection and molar response factors of human milk oligosaccharides. J Chromatogr B Biomed Appl. 1996 Oct 25;685(2):211-21. [PubMed:8953162 ]
  4. Coppa GV, Pierani P, Zampini L, Bruni S, Carloni I, Gabrielli O: Characterization of oligosaccharides in milk and feces of breast-fed infants by high-performance anion-exchange chromatography. Adv Exp Med Biol. 2001;501:307-14. [PubMed:11787695 ]
  5. Martin-Sosa S, Martin MJ, Garcia-Pardo LA, Hueso P: Sialyloligosaccharides in human and bovine milk and in infant formulas: variations with the progression of lactation. J Dairy Sci. 2003 Jan;86(1):52-9. [PubMed:12613848 ]
  6. Martin-Sosa S, Martin MJ, Hueso P: The sialylated fraction of milk oligosaccharides is partially responsible for binding to enterotoxigenic and uropathogenic Escherichia coli human strains. J Nutr. 2002 Oct;132(10):3067-72. [PubMed:12368397 ]