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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-24 15:50:47 UTC
Update Date2021-09-14 15:40:22 UTC
HMDB IDHMDB0006587
Secondary Accession Numbers
  • HMDB0006623
  • HMDB06587
  • HMDB06623
Metabolite Identification
Common NameLactodifucotetraose
DescriptionLactodifucotetraose (LDFT) is a fucosyloligosaccharide present in human milk and colostrum. Human colostrum is known to be important for the protection of infants against infection by pathogenic microorganisms. This protection is thought to be due, partially, to various neutral and acidic oligosaccharides that are present in colostrum and milk. Lactodifucotetraose decreased substantially until day 5 in human milk and appeared to stabilize in the following days. (PMID: 15343178 , 17375110 , 2246719 ). Lactodifucotetraose is a normal blood-group-active oligosaccharide excreted as a component of the urine in type O (H) secretors. (PMID 510288 ).
Structure
Thumb
Synonyms
ValueSource
O-6-Deoxy-alpha-L-galactopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->4)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->3)]-D-glucopyranose (8CL)HMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->2)-O-beta-delta-galactopyranosyl-(1->4)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->3)]-delta-glucopyranose (8CL)HMDB
O-alpha-L-Fucopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->4)-O-[alpha-L-fucopyranosyl-(1->3)]-glucopyranose (7ci)HMDB
O-alpha-L-Fucopyranosyl-(1->2)-O-beta-delta-galactopyranosyl-(1->4)-O-[alpha-L-fucopyranosyl-(1->3)]-glucopyranose (7ci)HMDB
3,2'-DifucosyllactoseMeSH, HMDB
3,2'-DLMeSH, HMDB
Chemical FormulaC24H42O19
Average Molecular Weight634.5789
Monoisotopic Molecular Weight634.232029162
IUPAC Name(2R,3S,4R,5R)-2-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5,6-trihydroxy-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexanal
Traditional Namelactodifucotetraose
CAS Registry Number20768-11-0
SMILES
C[C@@H]1O[C@@H](O[C@@H]([C@H](O)[C@H](O)CO)[C@@H](O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]2O)C=O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C24H42O19/c1-6-11(29)15(33)18(36)22(38-6)42-20(13(31)8(28)3-25)10(5-27)41-24-21(17(35)14(32)9(4-26)40-24)43-23-19(37)16(34)12(30)7(2)39-23/h5-26,28-37H,3-4H2,1-2H3/t6-,7-,8+,9+,10-,11+,12+,13+,14-,15+,16+,17-,18-,19-,20+,21+,22-,23-,24+/m0/s1
InChI KeyBRHHWBDLMUBZQQ-JZEMXWCPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty alcohol
  • Oxane
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aldehyde
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
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 Quantified0.47 uMAdult (>18 years old)FemaleNormal details
Breast MilkDetected and Quantified266 +/- 199 uMAdult (>18 years old)Female
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023987
KNApSAcK IDNot Available
Chemspider ID2339636
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3082169
PDB IDNot Available
ChEBI ID89917
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceTakeo, Kenichi; Tei, Saimei. Synthesis of lactodifucotetraose. Carbohydrate Research (1985), 141(1), 159-64.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Morrow AL, Ruiz-Palacios GM, Altaye M, Jiang X, Guerrero ML, Meinzen-Derr JK, Farkas T, Chaturvedi P, Pickering LK, Newburg DS: Human milk oligosaccharides are associated with protection against diarrhea in breast-fed infants. J Pediatr. 2004 Sep;145(3):297-303. [PubMed:15343178 ]
  2. Asakuma S, Urashima T, Akahori M, Obayashi H, Nakamura T, Kimura K, Watanabe Y, Arai I, Sanai Y: Variation of major neutral oligosaccharides levels in human colostrum. Eur J Clin Nutr. 2008 Apr;62(4):488-94. Epub 2007 Mar 21. [PubMed:17375110 ]
  3. Viverge D, Grimmonprez L, Cassanas G, Bardet L, Solere M: Variations in oligosaccharides and lactose in human milk during the first week of lactation. J Pediatr Gastroenterol Nutr. 1990 Oct;11(3):361-4. [PubMed:2246719 ]
  4. Chester MA, Hallgren P, Lundblad A, Messeter L: Urinary excretion of oligosaccharides induced by galactose given orally or intravenously. Eur J Biochem. 1979 Oct 15;100(2):385-92. [PubMed:510288 ]