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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-24 10:15:18 UTC
Update Date2021-09-14 15:46:05 UTC
HMDB IDHMDB0006566
Secondary Accession Numbers
  • HMDB06566
Metabolite Identification
Common NameLacto-N-tetraose
DescriptionLacto-N-tetraose (LNT) (CAS: 14116-68-8) is a neutral oligosaccharide present in human colostrum and milk. LNT is converted from lacto-N-triose II by the human enzyme beta-1,3-N-acetylglucosaminyltransferase 2 (beta3GnT2). Human milk is a unique reservoir of oligosaccharides. The presence of many of these oligosaccharides is determined genetically and is related to the Lewis blood group and secretor antigen status of each donor. Oligosaccharides in human milk represent a group of bioactive molecules that have evolved to be an abundant and diverse component of human milk, even though they have no direct nutritive value to the infant. A recent hypothesis proposes that they could be substrates for the development of the intestinal microflora and the mucosal immune system (PMID: 15629115 , 11787695 , 14530096 , 17002410 , 16277601 , 11787692 ).
Structure
Data?1582752392
Synonyms
Chemical FormulaC26H45NO21
Average Molecular Weight707.632
Monoisotopic Molecular Weight707.248407473
IUPAC NameN-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
Traditional NameN-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
CAS Registry Number7578-24-7
SMILES
CC(=O)N[C@H]1[C@H](O[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)O[C@@H]3CO)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C26H45NO21/c1-6(32)27-11-21(47-25-18(39)15(36)12(33)7(2-28)44-25)13(34)8(3-29)43-24(11)48-22-14(35)9(4-30)45-26(19(22)40)46-20-10(5-31)42-23(41)17(38)16(20)37/h7-26,28-31,33-41H,2-5H2,1H3,(H,27,32)/t7-,8-,9-,10-,11-,12+,13-,14+,15+,16-,17-,18-,19-,20-,21-,22+,23-,24+,25+,26+/m1/s1
InChI KeyAXQLFFDZXPOFPO-UNTPKZLMSA-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
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Organopnictogen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • beta-D-Gal-(1->3)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc (CHEBI:53481 )
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Breast Milk
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified506 +/- 284 uMAdult (>18 years old)Female
Normal
details
Breast MilkDetected and Quantified918.559(0-3872.082) uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019386
KNApSAcK IDNot Available
Chemspider ID4443269
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLacto-N-tetraose
METLIN IDNot Available
PubChem Compound5279514
PDB IDNot Available
ChEBI ID53481
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceYamashita, Katsuko; Tachibana, Yoko; Kobata, Akira. Oligosaccharides of human milk: structures of three lacto-N-hexaose derivatives with H-haptenic structure. Archives of Biochemistry and Biophysics (1977), 182(2), 546-55.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Deo VK, Park EY: Multiple co-transfection and co-expression of human beta-1,3-N-acetylglucosaminyltransferase with human calreticulin chaperone cDNA in a single step in insect cells. Biotechnol Appl Biochem. 2006 Mar;43(Pt 3):129-35. [PubMed:16277601 ]
  2. Ninonuevo MR, Park Y, Yin H, Zhang J, Ward RE, Clowers BH, German JB, Freeman SL, Killeen K, Grimm R, Lebrilla CB: A strategy for annotating the human milk glycome. J Agric Food Chem. 2006 Oct 4;54(20):7471-80. [PubMed:17002410 ]
  3. Coppa GV, Pierani P, Zampini L, Bruni S, Carloni I, Gabrielli O: Characterization of oligosaccharides in milk and feces of breast-fed infants by high-performance anion-exchange chromatography. Adv Exp Med Biol. 2001;501:307-14. [PubMed:11787695 ]
  4. Erney R, Hilty M, Pickering L, Ruiz-Palacios G, Prieto P: Human milk oligosaccharides: a novel method provides insight into human genetics. Adv Exp Med Biol. 2001;501:285-97. [PubMed:11787692 ]
  5. Chai W, Piskarev VE, Zhang Y, Lawson AM, Kogelberg H: Structural determination of novel lacto-N-decaose and its monofucosylated analogue from human milk by electrospray tandem mass spectrometry and 1H NMR spectroscopy. Arch Biochem Biophys. 2005 Feb 1;434(1):116-27. [PubMed:15629115 ]
  6. Von Seggern CE, Cotter RJ: Fragmentation studies of noncovalent sugar-sugar complexes by infrared atmospheric pressure MALDI. J Am Soc Mass Spectrom. 2003 Oct;14(10):1158-65. [PubMed:14530096 ]