N-Acetyllactosamine (CHEM033445)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:10:20 UTC
Update Date2016-11-09 01:20:55 UTC
Accession NumberCHEM033445
Identification
Common NameN-Acetyllactosamine
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
beta-D-Galactosyl-1,4-N-acetyl-D-glucosamineChEBI
Galb1-4glcnacbChEBI
Galbeta1-4glcnacbetaChEBI
LacNAcChEBI
N-Acetyl-beta-lactosamineChEBI
beta-D-Galactosyl-1,4-N-acetyl-beta-D-glucosamineKegg
b-D-Galactosyl-1,4-N-acetyl-D-glucosamineGenerator
Β-D-galactosyl-1,4-N-acetyl-D-glucosamineGenerator
N-Acetyl-b-lactosamineGenerator
N-Acetyl-β-lactosamineGenerator
b-D-Galactosyl-1,4-N-acetyl-b-D-glucosamineGenerator
Β-D-galactosyl-1,4-N-acetyl-β-D-glucosamineGenerator
beta-delta-Galactosyl-1,4-N-acetyl-beta-delta-glucosamineHMDB
beta-delta-Galactosyl-1,4-N-acetyl-delta-glucosamineHMDB
D-GalactopyranosylHMDB
delta-GalactopyranosylHMDB
N-Acetyl-lactosamineHMDB
ACETYL lactosamineHMDB
Chemical FormulaC28H50N2O22
Average Molecular Mass766.697 g/mol
Monoisotopic Mass766.286 g/mol
CAS Registry Number32181-59-2
IUPAC NameN-[(2R,3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
Traditional NameN-acetyllactosamine
SMILESCC(=O)NC(C=O)C(O)C(OC1OC(CO)C(O)C(O)C1O)C(O)CO.CC(=O)NC1C(O)OC(CO)C(OC2OC(CO)C(O)C(O)C2O)C1O
InChI IdentifierInChI=1S/2C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14;1-5(19)15-6(2-16)9(21)13(7(20)3-17)26-14-12(24)11(23)10(22)8(4-18)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18);2,6-14,17-18,20-24H,3-4H2,1H3,(H,15,19)
InChI KeyDWPBOAJUXRQZDI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • beta-D-galactopyranosyl-(1->4)-N-acetyl-D-glucosamine (CHEBI:16153 )
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility259 g/LALOGPS
logP-2.8ALOGPS
logP-5ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)11.5ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area198.4 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.44 m³·mol⁻¹ChemAxon
Polarizability35.66 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uy3-5539000000-9001b4ffdf2686f61fdbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0a4i-3410139000-490a44b54a788af499adSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0g4i-0294000000-eba3eabd1634e1f899d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002r-0900000000-65d60bd6a084f5fb8a03Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0019-9800000000-5cfef19dd8c8707bef7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00yi-0179000000-d117b299438bee3a1a40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0592000000-db6f5abfab26c98d8af4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0wbc-5960000000-915e1f050484eedb63d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2492000000-1208b9128bdb1fd8688eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h90-7984000000-2636a4af2a05389c39e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-7910000000-dce1bda7d8788ebd90afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-1169000000-37af2930ba0a18fdfe2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu3-9317000000-05676e3bb792b14a9ea9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9410000000-9f5dbeeb51b744740d72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8a-0659000000-98f0c5a2f817d77728acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0951000000-f475151e03af91aeeac3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9410000000-abd7ef88c6f0a3d44980Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001542
FooDB IDFDB019860
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID4231
PDB IDNot Available
Wikipedia LinkN-Acetyllactosamine
Chemspider ID388404
ChEBI ID16153
PubChem Compound ID439271
Kegg Compound IDC00611
YMDB IDNot Available
ECMDB IDM2MDB005453
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Dekany, Gyula; Agoston, Karoly; Bajza, Istvan; Boejstrup, Marie; Kroeger, Lars. Process for the large-scale preparation of N-acetyllactosamine, lactosamine, lactosamine salts and lactosamine-containing oligosaccharides. PCT Int. Appl. (2007), 44pp.
2. Jung SK, Fujimoto D: A novel beta-galactoside-binding lectin in adult rat kidney. J Biochem. 1994 Sep;116(3):547-53.
3. Yu LC, Twu YC, Chang CY, Lin M: Molecular basis of the adult i phenotype and the gene responsible for the expression of the human blood group I antigen. Blood. 2001 Dec 15;98(13):3840-5.
4. Dabelsteen E, Buschard K, Hakomori S, Young WW: Pattern of distribution of blood group antigens on human epidermal cells during maturation. J Invest Dermatol. 1984 Jan;82(1):13-7.
5. Ahmed H, Pohl J, Fink NE, Strobel F, Vasta GR: The primary structure and carbohydrate specificity of a beta-galactosyl-binding lectin from toad (Bufo arenarum Hensel) ovary reveal closer similarities to the mammalian galectin-1 than to the galectin from the clawed frog Xenopus laevis. J Biol Chem. 1996 Dec 20;271(51):33083-94.
6. Hosomi O, Takeya A: The relationship between the (beta 1-3) N-acetylglucosaminyltransferase and the presence of oligosaccharides containing lacto-N-triose II structure in bovine and human milk. Nihon Juigaku Zasshi. 1989 Feb;51(1):1-6.
7. Mollicone R, Candelier JJ, Mennesson B, Couillin P, Venot AP, Oriol R: Five specificity patterns of (1----3)-alpha-L-fucosyltransferase activity defined by use of synthetic oligosaccharide acceptors. Differential expression of the enzymes during human embryonic development and in adult tissues. Carbohydr Res. 1992 Apr 10;228(1):265-76.
8. Jinno K, Moriwaki S, Govindarajan S, Okada Y, Tsuji T: Blood group antigens in the intrahepatic biliary tree. II. Type 1 chain N-acetyllactosamine-related carbohydrate antigens in the proliferated bile ductules. J Hepatol. 1989 May;8(3):330-7.
9. Takeya A, Hosomi O, Kogure T: The presence of N-acetyllactosamine and lactose: beta (1-3)N-acetylglucosaminyltransferase activity in human urine. Jpn J Med Sci Biol. 1985 Feb;38(1):1-8.
10. Draberova L, Cerna H, Brodska H, Boubelik M, Watt SM, Stanners CP, Draber P: Soluble isoforms of CEACAM1 containing the A2 domain: increased serum levels in patients with obstructive jaundice and differences in 3-fucosyl-N-acetyl-lactosamine moiety. Immunology. 2000 Oct;101(2):279-87.
11. Kojima S, Eguchi H, Ookawara T, Fujiwara N, Yasuda J, Nakagawa K, Yamamura T, Suzuki K: Clostridium botulinum type A progenitor toxin binds to Intestine-407 cells via N-acetyllactosamine moiety. Biochem Biophys Res Commun. 2005 Jun 3;331(2):571-6.
12. Hosomi O, Takeya A, Kogure T: Human serum contains N-acetyllactosamine: beta 1-3 N-acetylglucosaminyltransferase activity. J Biochem. 1984 Jun;95(6):1655-9.
13. Dabelsteen E, Holbrook K, Clausen H, Hakomori S: Cell surface carbohydrate changes during embryonic and fetal skin development. J Invest Dermatol. 1986 Jul;87(1):81-5.
14. Argueso P, Spurr-Michaud S, Tisdale A, Gipson IK: Variation in the amount of T antigen and N-acetyllactosamine oligosaccharides in human cervical mucus secretions with the menstrual cycle. J Clin Endocrinol Metab. 2002 Dec;87(12):5641-8.
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=11181561
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=11429474
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=14631106
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=14672941
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=16966407
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=18280060
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=18849325
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=19443021
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=19486884
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=21496117
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=2457603
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=25568069
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=26802542
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=31537530
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=7706263
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=8737251