ChemFOnt: Showing chemical card for Lactodifucotetraose (CFc000002828)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:48 UTC

Chemfont ID

CFc000002828

Molecule Identification

Common Name

Lactodifucotetraose

Definition

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 , 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
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'-Difucosyllactose	MeSH, HMDB
3,2'-DL	MeSH, HMDB

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 Name

lactodifucotetraose

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

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Breast milk (PMID: 11787698)
Breast milk (HMDB: HMDB0006587)

Cellular substructure

Cytoplasm (HMDB: HMDB0006587)
Cell membrane (HMDB: HMDB0006587)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006587)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006587)

Source

Endogenous

Endogenous (HMDB: HMDB0006587)

Animal

Animal (HMDB: HMDB0006587)

Exogenous

Food

Food (HMDB: HMDB0006587)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006587)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006587)

Lipid metabolism pathway (HMDB: HMDB0006587)

Biochemical process

Lipid transport (HMDB: HMDB0006587)

Role

Biological role

Energy source (HMDB: HMDB0006587)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	119 g/L	ALOGPS
logP	-2	ALOGPS
logP	-6.8	ChemAxon
logS	-0.73	ALOGPS
pKa (Strongest Acidic)	11.66	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	315.21 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	131.5 m³·mol⁻¹	ChemAxon
Polarizability	59.58 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0006587

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023987

KNApSAcK ID

Not Available

Chemspider ID

2339636

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3082169

PDB ID

Not Available

ChEBI ID

89917

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Takeo, Kenichi; Tei, Saimei. Synthesis of lactodifucotetraose. Carbohydrate Research (1985), 141(1), 159-64.

Showing chemical card for Lactodifucotetraose (CFc000002828)

MOL for CFc000002828 (Lactodifucotetraose)

3D MOL for CFc000002828 (Lactodifucotetraose)

3D SDF for CFc000002828 (Lactodifucotetraose)

3D-SDF for CFc000002828 (Lactodifucotetraose)

PDB for CFc000002828 (Lactodifucotetraose)

3D PDB for CFc000002828 (Lactodifucotetraose)

SMILES for CFc000002828 (Lactodifucotetraose)

INCHI for CFc000002828 (Lactodifucotetraose)

Structure for CFc000002828 (Lactodifucotetraose)

3D Structure for CFc000002828 (Lactodifucotetraose)