Showing Compound Lacto-N-fucopentaose-2 (FDB023979)

Record Information

Version

1.0

Creation date

2011-09-21 00:37:54 UTC

Update date

2015-07-21 06:57:57 UTC

Primary ID

FDB023979

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Lacto-N-fucopentaose-2

Description

Lacto-N-fucopentaose-2 is an oligosaccharide found in human milk and other biofluids. Lacto-N-fucopentaose-2 is an active pentasaccharide of the blood group Lewisa (Lea). Oligosaccharides of the blood group family decorate diverse glycoproteins and glycolipids on the surface of cells. Lacto-N-fucopentaose-2 and its sulfated and sialylated analogs, SuLNFPII and SLNFPII, are potent oligosaccharide ligands for the animal lectins, E- and L-selectin, and the natural killer cell receptor, NKR-P1. (PMID: 8639679) [HMDB]

CAS Number

21973-23-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
Lacto-N-fucopentaose II	MeSH
Lacto-N-fucopentaose-2	hmdb
Lea penta	HMDB
LNF II	HMDB
LNFP II	MeSH
N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)-4-{[(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}oxan-3-yl]ethanimidate	Generator, HMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-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-alpha-L-galactopyranosyl-(1->4)-O-[beta-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-alpha-L-galactopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-glucose	HMDB
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-beta-D-galactopyranosyl-(1->4)- D-Glucose	hmdb

Showing 1 to 10 of 18 entries

Predicted Properties

Property	Value	Source
Water Solubility	106 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-9.9	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	11.41	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	25	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	423.46 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	176.56 m³·mol⁻¹	ChemAxon
Polarizability	81.32 Å³	ChemAxon
Number of Rings	4	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

C32H55NO25

IUPAC name

N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)-4-{[(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}oxan-3-yl]acetamide

InChI Identifier

InChI=1S/C32H55NO25/c1-8-16(42)20(46)22(48)30(51-8)56-26-14(7-38)54-29(15(33-9(2)39)27(26)57-31-23(49)21(47)18(44)12(5-36)52-31)58-28-19(45)13(6-37)53-32(24(28)50)55-25(11(41)4-35)17(43)10(40)3-34/h3,8,10-32,35-38,40-50H,4-7H2,1-2H3,(H,33,39)/t8-,10-,11+,12+,13+,14+,15+,16+,17+,18-,19-,20+,21-,22-,23+,24+,25+,26+,27+,28-,29-,30-,31-,32-/m0/s1

InChI Key

FKADDOYBRRMBPP-QKPOUJQKSA-N

Isomeric SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@H]3[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]3O)[C@H](NC(C)=O)[C@H]2O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@@H]1O

Average Molecular Weight

853.7708

Monoisotopic Molecular Weight

853.306316315

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
Beta-hydroxy aldehyde
Fatty acyl
Oxane
Acetamide
Alpha-hydroxyaldehyde
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Organopnictogen compound
Aldehyde
Primary alcohol
Organic nitrogen compound
Organonitrogen 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, Positive	splash10-007x-0701019150-61c29c3675d7faea183c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01po-3902047100-ba36751bb3cacf446ed5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01po-5900077210-ab7eefa27af17fee3901	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9433005780-8c12cd7bbf22c035e132	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05e9-8806029180-3b4b2e609369de380435	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-6933200000-c502b58ab4cb19add026	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0200049130-147a7f4703369dc2c2e1	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0007-6600089250-fc465433cebf68ea53ef	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ow-9600030100-d7de39285de6561e05ba	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3400000690-f3d4e9205ccc4d735a3e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0m07-5600000940-5ed742b08f1ab1a76990	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000022000-f99b9d21cbe7efbc0580	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

146972

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

168012

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06577

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

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Lacto-N-fucopentaose-2 (FDB023979)

Structure for FDB023979 (Lacto-N-fucopentaose-2)