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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:47:07 UTC
NP-MRD IDNP0000163
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Acetyllactosamine
DescriptionN-Acetyllactosamine, also known as galb1-4glcnacb or lacnac, 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. N-Acetyllactosamine exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
beta-D-Galactosyl-1,4-N-acetyl-D-glucosamineChEBI
Galb1-4glcnacbChEBI
Galbeta1-4glcnacbetaChEBI
LacNAcChEBI
N-Acetyl-beta-lactosamineChEBI
WURCS=2.0/2,2,1/[a2122h-1b_1-5_2*ncc/3=o][a2112h-1b_1-5]/1-2/a4-b1ChEBI
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 FormulaC14H25NO11
Average Mass383.3484 Da
Monoisotopic Mass383.14276 Da
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
CAS Registry Number32181-59-2
SMILES
CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H]1O
InChI Identifier
InChI=1S/C14H25NO11/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/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8+,9-,10+,11-,12-,13-,14+/m1/s1
InChI KeyKFEUJDWYNGMDBV-LODBTCKLSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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 )
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001542
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019860
KNApSAcK IDNot Available
Chemspider ID388404
KEGG Compound IDC00611
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Acetyllactosamine
METLIN ID4231
PubChem Compound439271
PDB IDNot Available
ChEBI ID16153
Good Scents IDrw1683271
References
General References
  1. Jung SK, Fujimoto D: A novel beta-galactoside-binding lectin in adult rat kidney. J Biochem. 1994 Sep;116(3):547-53. [PubMed:7852273 ]
  2. 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. [PubMed:1366057 ]
  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. [PubMed:11739194 ]
  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. [PubMed:6361167 ]
  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. [PubMed:8955156 ]
  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. [PubMed:2522567 ]
  7. 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. [PubMed:2732447 ]
  8. 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. [PubMed:3160874 ]
  9. 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. [PubMed:11012782 ]
  10. 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. [PubMed:15850798 ]
  11. 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. [PubMed:6236210 ]
  12. 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. [PubMed:3522754 ]
  13. 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. [PubMed:12466366 ]