Compound: sialyl Lewis x
SMILES: O=C(O)[C@@]1(O[C@H]([C@H](NC(=O)C)[C@H](C1)O)[C@H](O)[C@H](O)CO)O[C@@H]2[C@@H](O)[C@@H](O[C@@H]([C@@H]2O)CO)O[C@@H]([C@H](O[C@@H]3O[C@H]([C@@H](O)[C@H]([C@@H]3O)O)C)[C@@H](NC(=O)C)C=O)[C@H](O)CO
InChIKey: LAQPKDLYOBZWBT-NYLDSJSYSA-N
Synonyms: sialyl Lewis x, 98603-84-0, sialyl LewisX, Sialyl lewis-x, 0PS35WG8U3, sialyl-Lex, Lewis X, Sialyl, sialyl Le(x), CD15s Antigen, D-GLUCOSE, O-(N-ACETYL-.ALPHA.-NEURAMINOSYL)-(2->3)-O-.BETA.-D-GALACTOPYRANOSYL-(1->4)-O-(6-DEOXY-.ALPHA.-L-GALACTOPYRANOSYL-(1->3))-2-(ACETYLAMINO)-2-DEOXY-, D-Glucose, O-(N-acetyl-alpha-neuraminosyl)-(2->3)-o-beta-D-galactopyranosyl-(1->4)-O-(6-deoxy-alpha-L-galactopyranosyl-(1->3))-2-(acetylamino)-2-deoxy-, Antigen, CD15s, Sialyl SSEA 1, Sialyl SSEA-1, SLe(x)-OS, Sialyl Lewis(x) Antigen, Sialylated Lewis X Antigen, sialyl Lewis(x) tetrasaccharide, NAG-1,4-F-1,3-GN, Sialyl Stage Specific Embryonic Antigen 1, Sialyl Stage-Specific Embryonic Antigen-1, RefChem:389279, Neu5Ac-2-3-Gal-1-4-(Fuc-1-3)-GlcNAc, NeuAcalpha2-3Galbeta1-4(Fucalpha1-3)GlcNAc-R, alpha-Neu5Ac-(2-3)-beta-D-Gal-(1-4)-(alpha-L-Fuc-(1-3))-beta-D-GlcNAc, 5-acetylneuraminyl-(2-3)-galactosyl-(1-4)-(fucopyranosyl-(1-3))-N-acetylglucosamine, sialyl Lewis x antigen, sLe(X), Sialyl-Lewis X, 3'-Sialyl-Lewis X, SLex, Sialyl Lex tri, 3'-Sialyl-Lewis-X tetrasaccharide, 3'-SLeX, SSEA 1, (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5R)-5-acetamido-1,2-dihydroxy-6-oxo-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyhexan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid, a-NeuNAc-(2>3)-b-D-Gal-(1>4)(a-L-Fuc-[1>3])-D-GlcNAc, 3'-Sialyl Lewis X, sodium salt, 3a(2)-Sialyl-Lewis X, UNII-0PS35WG8U3, SCHEMBL346849, CHEMBL375586, orb1694233, DTXSID60913167, BDBM50450369, AKOS040754898, HY-W020790, OS04058, (2S,4S,5R,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3R,4R,5R)-5-acetamido-1,2-dihydroxy-6-oxo-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid, DA-67580, OS183415, NeuNAc-a2-3Gal-b1-4(Fuc-a1-3)GlcNAc, CS-0031944, NS00123065, Q3959958, 3 inverted exclamation marka-Sialyl-Lewis-X tetrasaccharide, alpha-NeuNAc-(2>3)-beta-delta-Gal-(1>4)(a-L-Fuc-[1>3])-delta-GlcNAc, (2S,4S,5R,6R)-5-Acetamido-2-(((2S,3R,4S,5S,6R)-2-(((2R,3R,4R,5R)-5-acetamido-1,2-dihydroxy-6-oxo-4-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)hexan-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid, (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(1R,2R,3R)-3-acetamido-1-[(1R)-1,2-dihydroxyethyl]-4-oxo-2-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-butoxy]-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid, 5-Acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranonosyl-(2->3)-beta-D-galactopyranosyl-(1->4)-[6-deoxy-alpha-L-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-D-glucose, D-Glucose, O-(N-acetyl-a-neuraminosyl)-(2>3)-O-b-D-galactopyranosyl-(1>4)-O-[6-deoxy-a-L-galactopyranosyl-(1>3)]-2-(acetylamino)-2-deoxy- (9CI), D-glucose, O-5-(acetylamino)-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranonosyl-(2>3)-O-beta-D-galactopyranosyl-(1>4)-O-[6-deoxy-alpha-L-galactopyranosyl-(1>3)]-2-(acetylamino)-2-deoxy-
Theoretical properties:
molecular_formula: C31H52N2O23
molecular_weight: 820.7 g/mol
exact_mass: 820.29608591 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 15
hydrogen_bond_acceptor_count: 23
rotatable_bond_count: 18
heavy_atom_count: 56
topological_polar_surface_area: 411 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: SIALYL LEWIS X is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Sialyl LewisX (sLeX), also known as cluster of differentiation 15s (CD15s) or stage-specific embryonic antigen 1 (SSEA-1), is a tetrasaccharide carbohydrate which is usually attached to O-glycans on the surface of cells. It is known to play a vital role in cell-to-cell recognition processes. It is also the means by which an egg attracts sperm; first, to stick to it, then bond with it and eventually form a zygote.
Sialyl-LewisX is also one of the most important blood group antigens and is displayed on the terminus of glycolipids that are present on the cell surface. The sialyl-LewisX determinant, E-selectin ligand carbohydrate structure, is constitutively expressed on granulocytes and monocytes and mediates inflammatory extravasation of these cells. Resting T and B lymphocytes lack its expression and are induced to strongly express sialyl-LewisX upon activation. The sialyl-LewisX determinant is expressed preferentially on activated Th1 cells but not on Th2 cells.