Showing metabocard for (N-acetylneuraminosyl(a2-6)lactosamine) (BMDB0001081)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:40:50 UTC
Update Date2020-06-04 20:03:52 UTC
MCDB ID BMDB0001081
Secondary Accession Numbers
  • BMDB01081
Metabolite Identification
Common Name(N-acetylneuraminosyl(a2-6)lactosamine)
Description(N-Acetylneuraminosyl(a2-6)lactosamine), also known as a-neunac-(2->6)-b-D-gal-(1->4)-b-D-glcnac or 6-sialyllactosamine, belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety (N-Acetylneuraminosyl(a2-6)lactosamine) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,4S,5R,6R)-5-Acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-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 acidChEBI
(N-Acetylneuraminosyl(alpha2-6)lactosamine)ChEBI
6'-SialyllactosamineChEBI
6-SialyllactosamineChEBI
alpha-N-Acetylneuraminyl-2,6-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamineChEBI
alpha-N-Acetylneuraminyl-2,6-beta-delta-galactosyl-1,4-N-acetyl-beta-delta-glucosamineChEBI
alpha-NeuNAc-(2->6)-beta-D-gal-(1->4)-beta-D-glcnacChEBI
alpha-NeupNAc-(2->6)-beta-D-galp-(1->4)-beta-D-glcpnacChEBI
N-Acetylneuraminosyl(alpha2-6)lactosamineChEBI
Neu5aca2-6galb1-4glcnacbChEBI
Neuac-lactChEBI
NeuAcalpha2,6galbeta1,4glcnacChEBI
Neuacalpha2,6galnacbeta1,4glcnacChEBI
Neuacalpha2-6galbeta1-4glcnacbetaChEBI
O-(N-Acetyl-a-neuraminosyl)-(2->6)-O-b-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-b-D-glucopyranoseChEBI
O-(N-Acetyl-alpha-neuraminosyl)-(26)-O-beta-D-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranoseChEBI
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-delta-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-beta-delta-glucopyranoseChEBI
WURCS=2.0/3,3,2/[a2122h-1b_1-5_2*ncc/3=o][a2112h-1b_1-5][aad21122h-2a_2-6_5*ncc/3=o]/1-2-3/a4-b1_b6-C2ChEBI
(2R,4S,5R,6R)-5-Acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-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-carboxylateGenerator
(N-Acetylneuraminosyl(α2-6)lactosamine)Generator
a-N-Acetylneuraminyl-2,6-b-D-galactosyl-1,4-N-acetyl-b-D-glucosamineGenerator
Α-N-acetylneuraminyl-2,6-β-D-galactosyl-1,4-N-acetyl-β-D-glucosamineGenerator
a-N-Acetylneuraminyl-2,6-b-delta-galactosyl-1,4-N-acetyl-b-delta-glucosamineGenerator
Α-N-acetylneuraminyl-2,6-β-δ-galactosyl-1,4-N-acetyl-β-δ-glucosamineGenerator
a-NeuNAc-(2->6)-b-D-gal-(1->4)-b-D-glcnacGenerator
Α-neunac-(2->6)-β-D-gal-(1->4)-β-D-glcnacGenerator
a-NeupNAc-(2->6)-b-D-galp-(1->4)-b-D-glcpnacGenerator
Α-neupnac-(2->6)-β-D-galp-(1->4)-β-D-glcpnacGenerator
N-Acetylneuraminosyl(a2-6)lactosamineGenerator
N-Acetylneuraminosyl(α2-6)lactosamineGenerator
O-(N-Acetyl-a-neuraminosyl)-(26)-O-b-D-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-b-D-glucopyranoseGenerator
O-(N-Acetyl-α-neuraminosyl)-(26)-O-β-D-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-β-D-glucopyranoseGenerator
O-(N-Acetyl-a-neuraminosyl)-(2->6)-O-b-delta-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-b-delta-glucopyranoseGenerator
O-(N-Acetyl-α-neuraminosyl)-(2->6)-O-β-δ-galactopyranosyl-(1->-4)-2-(acetylamino)-2-deoxy-β-δ-glucopyranoseGenerator
Neu5acbeta2-6galbeta1-4glcnacbetaChEBI, HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-delta-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-delta-glucopyranoseHMDB
a-N-Acetylneuraminyl-(2->6)-b-D-galactosyl-(1->4)-N-acetyl-b-D-glucosamineGenerator, HMDB
Α-N-acetylneuraminyl-(2->6)-β-D-galactosyl-(1->4)-N-acetyl-β-D-glucosamineGenerator, HMDB
Chemical FormulaC25H42N2O19
Average Molecular Weight674.603
Monoisotopic Molecular Weight674.238177172
IUPAC Name(2R,4S,5R,6R)-5-acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-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 Name6-sialyllactosamine
CAS Registry Number64364-50-7
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@H](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-LURNZOHQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentNeuraminic acids
Alternative Parents
Substituents
  • Neuraminic acid
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • C-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Pyran
  • Oxane
  • Hemiacetal
  • Secondary alcohol
  • Acetal
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Polyol
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Primary alcohol
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability63.23 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nmi-5235119000-5a6aa8ff9e0838274a4b2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_12) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_13) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0avi-0051009000-92d7600cf12a3e43b8da2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4i-2294002000-8d29637be46c1d8fd36f2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-022c-4391001000-847f9d4addc27d2b4d8d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-4942473000-7edd91cc87dbeead80222017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05g0-9881203000-a60297bc793daed18eb22017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9641000000-bc983c803272c7ccce3c2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0020039000-18d48851f2beb9db3adf2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3090022000-8c7f3399bee970f68a602021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-9520001000-9d39a2f319fe4cae1e7c2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000009000-6626f23b078e7b6b89e82021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0267029000-d0aa4fdac515d5c385532021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f8c-4987000000-3cdf54155f61766e67112021-09-22View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified13 - 18 uM
  • International Dai...
 details
HMDB IDHMDB0001081
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022413
KNApSAcK IDNot Available
Chemspider ID111381
KEGG Compound IDC04886
BioCyc IDALPHA-N-ACETYLNEURAMINYL-26-BETA
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17725
References
Synthesis ReferenceDall'Olio F The sialyl-alpha2,6-lactosaminyl-structure: biosynthesis and functional role. Glycoconjugate journal (2000), 17(10), 669-76.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Paul McJarrow, Janneke van Amelsfort-Schoonbeek (2004). International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579. International Dairy Journal.