Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-24 12:38:02 UTC
Update Date2022-09-22 18:34:19 UTC
HMDB IDHMDB0006581
Secondary Accession Numbers
  • HMDB06581
Metabolite Identification
Common Name3-Sialyl-N-acetyllactosamine
Description3-Sialyl-N-acetyllactosamine is a normal sialyloligosaccharide that is present in human biofluids, and is one of the predominant oligosaccharides in human urine as a free form. The presence of these compounds in the urine is linked to the biosynthesis and degradation of the body glycoproteins, glycolipids, and glycans. Under certain pathological conditions, the total urinary carbohydrate-material is increased dramatically, and the number and ratios of the components present are also increased. Many of these pathological disorders are the result of a deficiency in a specific exoglycosidase. 3-Sialyl-N-acetyllactosamine have a sialyl(a2-3) linkage and is of interest in view of the discovery of uropathogenic Escherichia coli strains with binding specificity for sialyl(a2-3)galactosides. (PMID: 2445744 ; 2775488; 3813552; 6619126; 6628386; 6628680; 6714239; 6746638; 7925342).
Structure
Data?1582752393
Synonyms
ValueSource
NeuAc(a2-3)gal(b1-4)glcnacHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-D-glucoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-delta-glucoseHMDB
(2R,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-4,5-dihydroxy-6-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-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(2R,4S,5R,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-6-acetamido-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2R,4S,5R,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-6-acetamido-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry Number81693-22-3
SMILES
[H][C@]1(O[C@](C[C@H](O)[C@H]1NC(C)=O)(O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(NC(C)=O)O[C@@H]2CO)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C25H42N2O19/c1-7(31)26-13-9(33)3-25(24(40)41,45-20(13)14(35)10(34)4-28)46-21-15(36)11(5-29)43-23(18(21)39)44-19-12(6-30)42-22(27-8(2)32)17(38)16(19)37/h9-23,28-30,33-39H,3-6H2,1-2H3,(H,26,31)(H,27,32)(H,40,41)/t9-,10+,11+,12+,13+,14+,15-,16+,17+,18+,19+,20+,21-,22?,23-,25+/m0/s1
InChI KeyHUNVSYPDCXFGLB-KROWHOKKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy aldehyde
  • Fatty acyl
  • Oxane
  • Acetamide
  • Alpha-hydroxyaldehyde
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Aldehyde
  • Primary alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • 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 Solubility66.1 g/LALOGPS
logP-2.7ALOGPS
logP-7.4ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
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
Polarizability63.55 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]+234.25730932474
DeepCCS[M-H]-232.53330932474
DeepCCS[M-2H]-266.97430932474
DeepCCS[M+Na]+240.49730932474
AllCCS[M+H]+241.532859911
AllCCS[M+H-H2O]+240.932859911
AllCCS[M+NH4]+242.032859911
AllCCS[M+Na]+242.132859911
AllCCS[M-H]-241.832859911
AllCCS[M+Na-2H]-243.732859911
AllCCS[M+HCOO]-246.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Sialyl-N-acetyllactosamine[H][C@]1(O[C@](C[C@H](O)[C@H]1NC(C)=O)(O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(NC(C)=O)O[C@@H]2CO)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO4554.1Standard polar33892256
3-Sialyl-N-acetyllactosamine[H][C@]1(O[C@](C[C@H](O)[C@H]1NC(C)=O)(O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(NC(C)=O)O[C@@H]2CO)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO4565.4Standard non polar33892256
3-Sialyl-N-acetyllactosamine[H][C@]1(O[C@](C[C@H](O)[C@H]1NC(C)=O)(O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(NC(C)=O)O[C@@H]2CO)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO5338.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-6232209000-5b7d6c6c816d1b9d8fda2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_1_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_1_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sialyl-N-acetyllactosamine GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-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 - 3-Sialyl-N-acetyllactosamine 10V, Positive-QTOFsplash10-0r7i-2053009000-262ffb7e397c48a776f22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sialyl-N-acetyllactosamine 20V, Positive-QTOFsplash10-030r-3169000000-0150ae510e69112040572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sialyl-N-acetyllactosamine 40V, Positive-QTOFsplash10-03k9-9484000000-729e2465d486ef55b27c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sialyl-N-acetyllactosamine 10V, Negative-QTOFsplash10-05fu-5451119000-e569cd69c456636776452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sialyl-N-acetyllactosamine 20V, Negative-QTOFsplash10-0a4r-9563101000-7cf7327ae93e0b1b0df22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sialyl-N-acetyllactosamine 40V, Negative-QTOFsplash10-0a4i-9772000000-6848a76c652edc45be202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sialyl-N-acetyllactosamine 10V, Negative-QTOFsplash10-00di-0040039000-99a801b5f96724398d722021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sialyl-N-acetyllactosamine 20V, Negative-QTOFsplash10-053r-5191156000-6691a61fdbd0bd08e7172021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sialyl-N-acetyllactosamine 40V, Negative-QTOFsplash10-0006-9850100000-a47bfe8ff6f6937967ea2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sialyl-N-acetyllactosamine 10V, Positive-QTOFsplash10-056r-0000119000-d0e2677b25801bdcaddc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sialyl-N-acetyllactosamine 20V, Positive-QTOFsplash10-05o0-0024249000-2000919010f7058b38ce2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sialyl-N-acetyllactosamine 40V, Positive-QTOFsplash10-0fkc-9300001000-5c1c76cdf00b3685174e2021-09-25Wishart 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 QuantifiedAdult (>18 years old)FemaleEpithelial ovarian cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023983
KNApSAcK IDNot Available
Chemspider ID17216382
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16213476
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceScudder, Peter R.; Shailubhai, Kunwar; Duffin, Kevin L.; Streeter, Philip R.; Jacob, Gary S. Enzymic synthesis of a 6'-sulfated sialyl-Lewisx which is an inhibitor of L-selectin binding to peripheral addressin. Glycobiology (1994), 4(6), 929-32.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Edge AS, Spiro RG: Presence of an O-glycosidically linked hexasaccharide in fetuin. J Biol Chem. 1987 Nov 25;262(33):16135-41. [PubMed:2445744 ]