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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-24 12:18:38 UTC
Update Date2020-02-26 21:26:33 UTC
HMDB IDHMDB0006580
Secondary Accession Numbers
  • HMDB06580
Metabolite Identification
Common NameLacto-N-difucohexaose
DescriptionLacto-N-difucohexaose (LDFH) 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. Moderate-to-severe diarrhea of all causes occurs less often in infants whose milk contains high levels of total 2-linked fucosyloligosaccharides as a percent of milk oligosaccharide. Calicivirus diarrhea occurs less often in infants whose mother's milk contains high levels of LDFH. (PMID: 15343178 , 17375110 , 12568665 ).
Structure
Data?1582752393
Synonyms
ValueSource
Lacto-N-difucohexaose IHMDB
LND 1HMDB
LND IHMDB
LNDFH-IHMDB
O-6-Deoxy-a-L-galactopyranosyl-(1->2)-O-b-D-galactopyranosyl-(1->3)-O-[6-deoxy-a-L-galactopyranosyl-(1->4)]-O-2-acetamido-2-deoxy-b-D-glucopyranosyl-(1->3)-O-b-D-galactopyranosyl-(1->4)-D-glucopyranoseHMDB
O-6-Deoxy-a-L-galactopyranosyl-(1->4)-O-[O-6-deoxy-a-L-galactopyranosyl-(1->2)-b-D-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1->3)-O-b-D-galactopyranosyl-(1->4)-D-glucoseHMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->4)]-O-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucopyranoseHMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucoseHMDB
N-[(2R,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R)-4-{[(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}-6-hydroxy-1-oxo-2-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidateGenerator
Chemical FormulaC38H65NO29
Average Molecular Weight999.912
Monoisotopic Molecular Weight999.364225123
IUPAC NameN-[(2R,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R)-4-{[(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}-6-hydroxy-1-oxo-2-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional NameN-[(2R,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R)-4-{[(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}-6-hydroxy-1-oxo-2-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
CAS Registry Number16789-38-1
SMILES
C[C@@H]1O[C@@H](O[C@H](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@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@@H](O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)C=O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C38H65NO29/c1-9-18(46)24(52)28(56)35(59-9)64-16(8-44)32(67-38-33(27(55)22(50)14(6-42)63-38)68-36-29(57)25(53)19(47)10(2)60-36)31(15(7-43)65-37-30(58)26(54)21(49)13(5-41)62-37)66-34-17(39-11(3)45)23(51)20(48)12(4-40)61-34/h7,9-10,12-38,40-42,44,46-58H,4-6,8H2,1-3H3,(H,39,45)/t9-,10-,12+,13+,14+,15-,16+,17+,18+,19+,20+,21-,22-,23+,24+,25+,26-,27-,28-,29-,30+,31+,32+,33+,34+,35-,36-,37+,38+/m0/s1
InChI KeyPSJVAGXZRSPYJB-UUXGNFCPSA-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
  • Fatty acyl
  • Oxane
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Carbonyl group
  • Aldehyde
  • Primary alcohol
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

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 Solubility175 g/LALOGPS
logP-2ALOGPS
logP-11ChemAxon
logS-0.76ALOGPS
pKa (Strongest Acidic)11.41ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count29ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area482.38 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity207.43 m³·mol⁻¹ChemAxon
Polarizability93.21 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00el-1100027194-d0a3b1ed91774365d72aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-0100039141-b5d6bef1b4aa3a7db72cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-4420059142-ee76e600a06c10e394d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-2501015977-3b2eee873f6a3c935152Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-1910017136-e17831ccb3aecc7d9800Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-3900011210-bd9426601aa600351867Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Breast Milk
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified0.550 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023982
KNApSAcK IDNot Available
Chemspider ID2339585
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3082109
PDB IDNot Available
ChEBI ID89922
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
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. Sumiyoshi W, Urashima T, Nakamura T, Arai I, Saito T, Tsumura N, Wang B, Brand-Miller J, Watanabe Y, Kimura K: Determination of each neutral oligosaccharide in the milk of Japanese women during the course of lactation. Br J Nutr. 2003 Jan;89(1):61-9. [PubMed:12568665 ]