Showing Compound Lacto-N-difucohexaose (FDB023982)

Record Information

Version

1.0

Creation date

2011-09-21 00:37:57 UTC

Update date

2015-07-21 06:57:57 UTC

Primary ID

FDB023982

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Lacto-N-difucohexaose

Description

Lacto-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) [HMDB]

CAS Number

16789-38-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
Lacto-N-difucohexaose	hmdb
Lacto-N-difucohexaose I	MeSH
LND 1	HMDB
LND I	HMDB
LNDFH-I	HMDB
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]ethanimidate	Generator, HMDB
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-glucopyranose	HMDB
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-Glucopyranose	hmdb
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-glucose	HMDB
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-Glucose	hmdb

Showing 1 to 10 of 14 entries

Predicted Properties

Property	Value	Source
Water Solubility	175 g/L	ALOGPS
logP	-2	ALOGPS
logP	-11	ChemAxon
logS	-0.76	ALOGPS
pKa (Strongest Acidic)	11.41	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	29	ChemAxon
Hydrogen Donor Count	18	ChemAxon
Polar Surface Area	482.38 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	207.43 m³·mol⁻¹	ChemAxon
Polarizability	93.21 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C38H65NO29

IUPAC name

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]acetamide

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 Key

PSJVAGXZRSPYJB-UUXGNFCPSA-N

Isomeric 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

Average Molecular Weight

999.912

Monoisotopic Molecular Weight

999.364225123

Classification

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
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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Biological location:

Biofluid and excreta:

Breast milk

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01q9-2501015977-3b2eee873f6a3c935152	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03e9-1910017136-e17831ccb3aecc7d9800	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03fr-3900011210-bd9426601aa600351867	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-0100000139-747f2d69bfdd3bf7f31d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-9601000058-3336b5b612d3d433f143	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-9210055052-5780c2f57b0e2a457b12	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00el-1100027194-d0a3b1ed91774365d72a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-0100039141-b5d6bef1b4aa3a7db72c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-4420059142-ee76e600a06c10e394d6	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uei-5032003098-59e98a950bca4ac4f40d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uel-4902005252-cf0830c4aae88c606648	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-003g-9300010011-7b047c2c81810697928e	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

2339585

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

3082109

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06580

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Lacto-N-difucohexaose (FDB023982)

Structure for FDB023982 (Lacto-N-difucohexaose)