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Human Metabolome Database Version 3.5

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Showing metabocard for Lactodifucotetraose (HMDB06587)

Record Information
Version 3.5
Creation Date 2007-05-24 09:50:47 -0600
Update Date 2013-02-08 17:15:03 -0700
HMDB ID HMDB06587
Secondary Accession Numbers
  • HMDB06623
Metabolite Identification
Common Name Lactodifucotetraose
Description Lactodifucotetraose (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 Link_out, 17375110 Link_out, 2246719 Link_out). Lactodifucotetraose is a normal blood-group-active oligosaccharide excreted as a component of the urine in type O (H) secretors. (PMID 510288 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Lactodifucotetraose
  2. 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)
  3. 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)
  4. O-alpha-L-Fucopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->4)-O-[alpha-L-fucopyranosyl-(1->3)]-Glucopyranose (7CI)
  5. O-alpha-L-Fucopyranosyl-(1->2)-O-beta-delta-galactopyranosyl-(1->4)-O-[alpha-L-fucopyranosyl-(1->3)]-Glucopyranose (7CI)
Chemical Formula C24H42O19
Average Molecular Weight 634.5789
Monoisotopic Molecular Weight 634.232029162
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 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
CAS Registry Number 20768-11-0
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 Key BRHHWBDLMUBZQQ-JZEMXWCPSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Tetrasaccharides
Sub Class Tetrahexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Aldehyde
  • Fatty Acyl Glycoside
  • Fatty Alcohol
  • Glycosyl Compound
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
Direct Parent Tetrahexoses
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 119 g/L ALOGPS
LogP -2.03 ALOGPS
LogP -6.8 ChemAxon
LogS -0.73 ALOGPS
pKa (strongest acidic) 11.66 ChemAxon
pKa (strongest basic) -3.6 ChemAxon
Hydrogen Acceptor Count 19 ChemAxon
Hydrogen Donor Count 12 ChemAxon
Polar Surface Area 315.21 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 131.5 ChemAxon
Polarizability 59.58 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Breast Milk
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Breast Milk Detected and Quantified
Article_icon
0.47 uM Adult (>18 years old) Female Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023987
KNApSAcK ID Not Available
Chemspider ID 2339636 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06587 Link_out
Metagene Link HMDB06587 Link_out
METLIN ID Not Available
PubChem Compound 3082169 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Takeo, Kenichi; Tei, Saimei. Synthesis of lactodifucotetraose. Carbohydrate Research (1985), 141(1), 159-64.
Material Safety Data Sheet (MSDS) Not Available
General References Not Available