ChemFOnt: Showing chemical card for Sialyl Lex penta (CFc000002850)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:49 UTC

Chemfont ID

CFc000002850

Molecule Identification

Common Name

Sialyl Lex penta

Definition

In human leukocytes, sialyl Lex determinants bind selectins expressed on the blood vessel, endothelial cells and platelets, causing various cellular interactions and inducing inflammation. The sialyl Lex determinants of CD11/CD18 are shown to bind to E-selection in vitro, suggesting their involvement in the selectin-mediated adhesion process. ("Biology of the Sialic Acids" by Abraham Rosenberg).

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Chemical Formula

C₄₃H₇₂N₂O₃₃

Average Molecular Weight

1145.0254

Monoisotopic Molecular Weight

1144.40173284

IUPAC Name

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

Traditional Name

CAS Registry Number

127923-85-7

SMILES

C[C@@H]1OC(O[C@@H]2[C@@H](NC(C)=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)O[C@H](CO)[C@H]2O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@H](O3)C(O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@@H](O)[C@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C43H72N2O33/c1-11-23(58)28(63)29(64)39(69-11)75-35-22(45-13(3)53)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)72-20(10-51)33(35)74-41-31(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

MIEFTLKRJLOCFD-WXGLPKFQSA-N

Chemical Taxonomy

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

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0006614)

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	130 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-12	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	2.84	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	109 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

External Links

HMDB ID

HMDB0006614

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024005

KNApSAcK ID

Not Available

Chemspider ID

59651616

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750431

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Sialyl Lex penta (CFc000002850)

MOL for CFc000002850 (Sialyl Lex penta)

3D MOL for CFc000002850 (Sialyl Lex penta)

3D SDF for CFc000002850 (Sialyl Lex penta)

3D-SDF for CFc000002850 (Sialyl Lex penta)

PDB for CFc000002850 (Sialyl Lex penta)

3D PDB for CFc000002850 (Sialyl Lex penta)

SMILES for CFc000002850 (Sialyl Lex penta)

INCHI for CFc000002850 (Sialyl Lex penta)

Structure for CFc000002850 (Sialyl Lex penta)

3D Structure for CFc000002850 (Sialyl Lex penta)