ChemFOnt: Showing chemical card for Lacto-N-fucoheptaose (CFc000002862)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:50 UTC

Chemfont ID

CFc000002862

Molecule Identification

Common Name

Lacto-N-fucoheptaose

Definition

Lacto-N-fucoheptaose is a heptasaccharide found in human breast milk. It contains D(+)-galactose, D(+)-glucose, L(-)-fucose and N-acetyl-D(+)-glucosamine in a 3 : 1 : 1 : 2 ratio. The glucose residue is at the reducing end of the oligosaccharide. Milk oligosaccharides vary among individuals and over the course of lactation. Oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound oligosaccharides have potential biological activity and are known to inhibit viral infection. (PMID: 10744332 , 7138030 , 1132510 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-[O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)]-O-beta-D-galactopyranosyl-(1->4)- D-glucose	HMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-[O-beta-delta-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->6)]-O-beta-delta-galactopyranosyl-(1->4)- D-glucose	HMDB
N-[2-({3,5-dihydroxy-2-[({4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl}oxy)methyl]-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl}oxy)-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]ethanimidate	HMDB
Lacto-N-fucoheptaose	MeSH

Chemical Formula

C₄₆H₇₈N₂O₃₅

Average Molecular Weight

1219.1039

Monoisotopic Molecular Weight

1218.438512276

IUPAC Name

N-(2-{[2-({[3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,5-dihydroxy-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl)acetamide

Traditional Name

CAS Registry Number

56501-25-8

SMILES

CC1OC(OC2(CC(NC(C)=O)C(OC3C(O)C(COC4OC(CO)C(OC5OC(CO)C(O)C(O)C5O)C(O)C4NC(C)=O)OC(OC(C(O)CO)C(O)C(O)C=O)C3O)OC2CO)OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C46H78N2O35/c1-12-24(59)30(65)34(69)44(73-12)82-46(83-45-35(70)32(67)27(62)19(8-52)75-45)4-15(47-13(2)55)40(78-22(46)10-54)81-39-28(63)21(77-43(36(39)71)79-37(17(58)6-50)25(60)16(57)5-49)11-72-41-23(48-14(3)56)29(64)38(20(9-53)76-41)80-42-33(68)31(66)26(61)18(7-51)74-42/h5,12,15-45,50-54,57-71H,4,6-11H2,1-3H3,(H,47,55)(H,48,56)

InChI Key

DUUXDOCGEHMZIH-UHFFFAOYSA-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharides

Alternative Parents

Substituents

Oligosaccharide
Fatty acyl glycoside
N-acyl-alpha-hexosamine
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Ketal
Beta-hydroxy aldehyde
Oxane
Fatty acyl
Alpha-hydroxyaldehyde
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Organoheterocyclic compound
Polyol
Acetal
Oxacycle
Carboxylic acid derivative
Aldehyde
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organic nitrogen compound
Alcohol
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Feces (PMID: 23210743)

Source

Endogenous

Endogenous (HMDB: HMDB0006643)

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

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	152 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-13	ChemAxon
logS	-0.9	ALOGPS
pKa (Strongest Acidic)	11.36	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	35	ChemAxon
Hydrogen Donor Count	22	ChemAxon
Polar Surface Area	590.63 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	252.44 m³·mol⁻¹	ChemAxon
Polarizability	115.23 Å³	ChemAxon
Number of Rings	6	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

HMDB0006643

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024017

KNApSAcK ID

Not Available

Chemspider ID

2339104

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3081510

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Zhang Y; Dausse B; Sinay P; Afsahi M; Berthault P; Desvaux H Synthesis and NMR study of a heptasaccharide, epitope of the stage-specific embryonic antigen-1 (SSEA-1). Carbohydrate research (2000), 324(4), 231-41. PubMed ID 10744332

Showing chemical card for Lacto-N-fucoheptaose (CFc000002862)

MOL for CFc000002862 (Lacto-N-fucoheptaose)

3D MOL for CFc000002862 (Lacto-N-fucoheptaose)

3D SDF for CFc000002862 (Lacto-N-fucoheptaose)

3D-SDF for CFc000002862 (Lacto-N-fucoheptaose)

PDB for CFc000002862 (Lacto-N-fucoheptaose)

3D PDB for CFc000002862 (Lacto-N-fucoheptaose)

SMILES for CFc000002862 (Lacto-N-fucoheptaose)

INCHI for CFc000002862 (Lacto-N-fucoheptaose)

Structure for CFc000002862 (Lacto-N-fucoheptaose)

3D Structure for CFc000002862 (Lacto-N-fucoheptaose)