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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-24 13:12:01 UTC
Update Date2022-09-22 18:34:19 UTC
HMDB IDHMDB0006584
Secondary Accession Numbers
  • HMDB06584
Metabolite Identification
Common Name6-Sialyl-N-acetyllactosamine
Description6-Sialyl-N-acetyllactosamine is an oligosaccharide widely distributed among tissues and is involved in biological processes such as the regulation of the immune response and the progression of colon cancer. Sialylation represents one of the most frequently occurring terminations of the oligosaccharide chains of glycoproteins and glycolipids. Sialic acid is commonly found alpha,3- or alpha,6-linked to galactose (Gal), alpha,6-linked to N-acetylgalactosamine (GalNAc) or alpha,8-linked to another sialic acid. The biosynthesis of the various linkages is mediated by the different members of the sialyltransferase family. The b-galactoside a2,6 sialyltransferase (EC 2.4.99.1, ST6Gal.I) is the only sialyltransferase so far identified able to catalyze the a2,6-sialylation of lactosamine. Although expressed by a single gene, this enzyme shows a complex pattern of regulation which allows its tissue- and stage-specific modulation. The level of expression of the sialyl-alpha2,6-lactosaminyl structures and of ST6Gal.I show a strong dependence on neoplastic transformation and differentiation in several tissues. (PMID: 11425186 ).
Structure
Data?1582752393
Synonyms
ValueSource
6'-Sialyl-N-acetyllactosamineHMDB
62-a-N-Acetylneuraminyl-N-acetyllactosamHMDB
62-alpha-N-Acetylneuraminyl-N-acetyllactosamHMDB
62-alpha-N-Acetylneuraminyl-N-acetyllactosamineHMDB
NeuAc alpha,6gal beta1,4gicnacHMDB
O-(N-Acetyl-a-neuraminosyl)-(2->6)-O-b-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-D-glucoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-D-glucoseHMDB
(2S,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R)-4,6-dihydroxy-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, HMDB
Chemical FormulaC25H42N2O19
Average Molecular Weight674.603
Monoisotopic Molecular Weight674.238177172
IUPAC Name(2S,4S,5R,6R)-5-acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2S,4S,5R,6R)-5-acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry Number78969-47-8
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](NC(C)=O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C25H42N2O19/c1-7(30)26-13-9(32)3-25(24(40)41,46-21(13)15(34)10(33)4-28)42-6-12-16(35)18(37)19(38)23(44-12)45-20-11(5-29)43-22(39)14(17(20)36)27-8(2)31/h9-23,28-29,32-39H,3-6H2,1-2H3,(H,26,30)(H,27,31)(H,40,41)/t9-,10+,11+,12+,13+,14+,15+,16-,17+,18-,19+,20+,21+,22?,23-,25-/m0/s1
InChI KeyRPSBVJXBTXEJJG-RAMSCCQBSA-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
  • N-acylneuraminic acid
  • Acylaminosugar
  • Neuraminic acid
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • C-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Pyran
  • Oxane
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Hemiacetal
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Acetal
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organonitrogen compound
  • Primary 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 Solubility72.5 g/LALOGPS
logP-2.7ALOGPS
logP-7.4ChemAxon
logS-0.97ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area343.95 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity139.71 m³·mol⁻¹ChemAxon
Polarizability62.83 ųChemAxon
Number of Rings3ChemAxon
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]+229.59530932474
DeepCCS[M-H]-227.87130932474
DeepCCS[M-2H]-261.94830932474
DeepCCS[M+Na]+235.87230932474
AllCCS[M+H]+241.832859911
AllCCS[M+H-H2O]+241.232859911
AllCCS[M+NH4]+242.332859911
AllCCS[M+Na]+242.432859911
AllCCS[M-H]-241.932859911
AllCCS[M+Na-2H]-243.832859911
AllCCS[M+HCOO]-246.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-Sialyl-N-acetyllactosamine[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](NC(C)=O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)[C@H](O)CO4813.8Standard polar33892256
6-Sialyl-N-acetyllactosamine[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](NC(C)=O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)[C@H](O)CO4501.0Standard non polar33892256
6-Sialyl-N-acetyllactosamine[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](NC(C)=O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)[C@H](O)CO5435.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nmi-5235119000-5a6aa8ff9e0838274a4b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_1_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_1_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Sialyl-N-acetyllactosamine GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Sialyl-N-acetyllactosamine 10V, Positive-QTOFsplash10-0avi-0051009000-92d7600cf12a3e43b8da2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Sialyl-N-acetyllactosamine 20V, Positive-QTOFsplash10-0g4i-2294002000-8d29637be46c1d8fd36f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Sialyl-N-acetyllactosamine 40V, Positive-QTOFsplash10-022c-4391001000-847f9d4addc27d2b4d8d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Sialyl-N-acetyllactosamine 10V, Negative-QTOFsplash10-00dl-4942473000-7edd91cc87dbeead80222017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Sialyl-N-acetyllactosamine 20V, Negative-QTOFsplash10-05g0-9881203000-a60297bc793daed18eb22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Sialyl-N-acetyllactosamine 40V, Negative-QTOFsplash10-0ab9-9641000000-bc983c803272c7ccce3c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Sialyl-N-acetyllactosamine 10V, Positive-QTOFsplash10-004i-0000009000-6626f23b078e7b6b89e82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Sialyl-N-acetyllactosamine 20V, Positive-QTOFsplash10-00lr-0267029000-d0aa4fdac515d5c385532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Sialyl-N-acetyllactosamine 40V, Positive-QTOFsplash10-0f8c-4987000000-3cdf54155f61766e67112021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Sialyl-N-acetyllactosamine 10V, Negative-QTOFsplash10-00di-0020039000-18d48851f2beb9db3adf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Sialyl-N-acetyllactosamine 20V, Negative-QTOFsplash10-001i-3090022000-8c7f3399bee970f68a602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Sialyl-N-acetyllactosamine 40V, Negative-QTOFsplash10-052o-9520001000-9d39a2f319fe4cae1e7c2021-09-24Wishart 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
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023986
KNApSAcK IDNot Available
Chemspider ID17216384
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16212424
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis Referenceaulsen, Hans; Tietz, Holger. Building blocks of oligosaccharides. Part 43. Synthesis of trisaccharide units from N-acetylneuraminic acid and N-acetyllactosamine. Angewandte Chemie (1982), 94(12), 934-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Dall'Olio F: The sialyl-alpha2,6-lactosaminyl-structure: biosynthesis and functional role. Glycoconj J. 2000 Oct;17(10):669-76. [PubMed:11425186 ]