Showing Compound Sialyl Lewis(a) pentasaccharide (FDB023998)

Record Information

Version

1.0

Creation date

2011-09-21 00:38:16 UTC

Update date

2015-07-21 06:57:58 UTC

Primary ID

FDB023998

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Sialyl Lewis(a) pentasaccharide

Description

Sialyl Lewis^a pentasaccharide is a human E-selectin (endothelial adhesion molecule) ligand. The cell adhesion molecule E-selectin, which is expressed on cytokine-stimulated endothelial cells, binds to neutrophils, monocytes, and a subpopulation of memory T-cells. This protein has an established role at the initial stepins the recruitment of leukocytes to sites of inflammation, and there is also much interest in the part that it plays in the hematogenous spread of cancer cells. Interference with selectin binding results in inhibition of the later steps that promote leukocyte extravasation. There is therefore much interest in defining the ligands that support adhesion, as a lead to design of adhesion inhibitors that may serve as drugs for the treatment of disorders of inflammation and for minimizing risk of metastasis during surgical resections of tumors.

As predicted from the presence of a lectin-like module at the amino-terminal endof the extracellular domain, E-selectin is a carbohydrate-binding protein. The established ligands for E-selectin include a family of blood group-related fucooligosaccharides that occur as differentiation antigens of granulocytes and monocytes (Le^x and 3'-sialyl-Le^x) and of epithelial tumors (Le^a and 3'-sialyl-Le^a). Adhesion to the sialyl antigens is substantially greater than to the asialo analogues (PMID:7507478)

[HMDB]

CAS Number

84061-53-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2S,4S,5R,6R)-2-{[(2R,3R,5S,6R)-2-{[(2S,3R,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}-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	Generator, HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-alpha-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-glucose	HMDB
O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-alpha-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-Glucose	hmdb
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-alpha-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)- D-glucose	HMDB
O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-alpha-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)- D-Glucose	hmdb
Sialyl lewisa penta	Generator

Showing 1 to 6 of 6 entries

Predicted Properties

Property	Value	Source
Water Solubility	138 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-12	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	2.87	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	33	ChemAxon
Hydrogen Donor Count	21	ChemAxon
Polar Surface Area	569.01 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	236.83 m³·mol⁻¹	ChemAxon
Polarizability	107.45 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

C43H72N2O33

IUPAC name

(2S,4S,5R,6R)-2-{[(2R,3R,5S,6R)-2-{[(2S,3R,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}-3-acetamido-6-(hydroxymethyl)-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

InChI Identifier

InChI=1S/C43H72N2O33/c1-11-23(58)28(63)29(64)39(69-11)74-33-20(10-51)72-38(76-36-26(61)18(8-49)70-40(30(36)65)73-32(17(57)7-48)24(59)15(55)5-46)22(45-13(3)53)35(33)75-41-31(66)37(27(62)19(9-50)71-41)78-43(42(67)68)4-14(54)21(44-12(2)52)34(77-43)25(60)16(56)6-47/h5,11,14-41,47-51,54-66H,4,6-10H2,1-3H3,(H,44,52)(H,45,53)(H,67,68)/t11-,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-,39-,40-,41-,43-/m0/s1

InChI Key

DBXMZPZIFJCVQO-RKVJIPOWSA-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)C2O[C@@H]2O[C@H](CO)[C@H](O)C(O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@H](O3)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@@H](O)[C@H](O)[C@@H]1O

Average Molecular Weight

1145.0254

Monoisotopic Molecular Weight

1144.40173284

Classification

Description

Belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acylneuraminic acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

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	splash10-003r-1900002023-28fc197cc43f87bca476	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053l-2702014491-435e0cc2d1f5d7bc4840	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03el-6900043231-8fc411c03905fda0f148	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00c9-6911000000-c83250fa58c2729a22f3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0570-8914001020-ca187e1cc26a4807e349	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-7946400000-9c546e1f7461390fc8f5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-6930000001-9ae35dc643df44c60ae3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0cnm-9610000001-ad9f8b66aa35d0f66dfc	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100010001-92ecb7b05c90a9e18345	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001j-1700000029-efb6bfeb1f8e1e238e55	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01rw-6900000034-d4d89f79d9751f83431b	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9800001010-b3e7205f1c992d507b44	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

53477868

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06605

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 Sialyl Lewis(a) pentasaccharide (FDB023998)

Structure for FDB023998 (Sialyl Lewis(a) pentasaccharide)