ChemFOnt: Showing chemical card for Sialyl-Lewis X (CFc000002813)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:47 UTC

Chemfont ID

CFc000002813

Molecule Identification

Common Name

Sialyl-Lewis X

Definition

Carbohydrate antigen which is accumulated in various human cancer tissues and secreted into the blood stream. The carbohydrate moiety can be further modified with fucose or sialic acid. Monoclonal antibodies have been determined which can discriminate each subgroup of this antigen in the sera of cancer patients. Sialyl SSEA-1 antigen is particularly elevated in the sera of patients with a variety of tumors.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
SLex	ChEMBL, HMDB
Sialyl lewisx	ChEMBL, HMDB
Sialyl lewis-X	ChEMBL, HMDB
Sialyl lex	ChEMBL, HMDB
3'-Sialyl-lewis X	HMDB
3'-Sialyl-lewis-X tetrasaccharide	HMDB
3'-SLeX	HMDB
a-NeuNAc-(2>3)-b-D-gal-(1>4)(a-L-fuc-[1>3])-D-glcnac	HMDB
alpha-NeuNAc-(2>3)-beta-delta-gal-(1>4)(a-L-fuc-[1>3])-delta-glcnac	HMDB
Sialyl lex tri	HMDB
SSEA 1	HMDB, MeSH
3 alpha Fucosyl N acetyl lactosamine	MeSH, HMDB
3 alpha-Fucosyl-N-acetyl lactosamine	MeSH, HMDB
Antigen, lewis X	MeSH, HMDB
Antigens, CD15	MeSH, HMDB
CD15 Antigen	MeSH, HMDB
CD15 Antigens	MeSH, HMDB
Embryonic antigen-1, stage-specific	MeSH, HMDB
Galbeta(1-4)fucalpha(1-3)glcnac	MeSH, HMDB
Hapten X	MeSH, HMDB
Le(X) antigen	MeSH, HMDB
Leu m1 antigens	MeSH, HMDB
Leu-m1 antigens	MeSH, HMDB
Lewis X antigen	MeSH, HMDB
Lewis X hapten	MeSH, HMDB
SSEA 1 determinant	MeSH, HMDB
SSEA-1	MeSH, HMDB
SSEA-1 determinant	MeSH, HMDB
Stage specific embryonic antigen 1	MeSH, HMDB
Stage-specific embryonic antigen-1	MeSH, HMDB
X Antigen, lewis	MeSH, HMDB
X Hapten, lewis	MeSH, HMDB
(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3R,4R,5R)-1,2-dihydroxy-5-[(1-hydroxyethylidene)amino]-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-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	Generator, HMDB

Chemical Formula

C₃₁H₅₂N₂O₂₃

Average Molecular Weight

820.7442

Monoisotopic Molecular Weight

820.29608598

IUPAC Name

(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

Traditional Name

sialyl-lewis X

CAS Registry Number

98603-84-0

SMILES

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

InChI Identifier

InChI=1S/C31H52N2O23/c1-9-18(43)21(46)22(47)28(51-9)53-24(12(5-34)32-10(2)38)25(15(42)7-36)54-29-23(48)27(20(45)16(8-37)52-29)56-31(30(49)50)4-13(40)17(33-11(3)39)26(55-31)19(44)14(41)6-35/h5,9,12-29,35-37,40-48H,4,6-8H2,1-3H3,(H,32,38)(H,33,39)(H,49,50)/t9-,12-,13-,14+,15+,16+,17+,18+,19+,20-,21+,22-,23+,24+,25+,26+,27-,28-,29-,31-/m0/s1

InChI Key

LAQPKDLYOBZWBT-NYLDSJSYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamine and derivatives

Alternative Parents

Substituents

Glutamine or derivatives
Glutamic acid or derivatives
Hippuric acid or derivatives
Pterin
Alpha-amino acid
Aminobenzamide
Aminobenzoic acid or derivatives
Pteridine
L-alpha-amino acid
Benzoic acid or derivatives
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Gamma-keto acid
Aminopyrimidine
Aralkylamine
Beta-keto acid
Amino fatty acid
Pyrimidone
Secondary aliphatic/aromatic amine
Gamma-aminoketone
Pyrimidine
Pyrazine
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Keto acid
N-acyl-amine
Carboxylic acid imide, n-substituted
Heteroaromatic compound
Carboxylic acid anhydride
Carboxylic acid imide
Dicarboximide
Vinylogous amide
Ketone
Amino acid
Secondary amine
Carboxylic acid
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Carbonyl group
Amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Primary amine
Organooxygen compound
Organic oxide
Primary aliphatic amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0006565)

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	45.5 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-8.8	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	2.84	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	410.71 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	172 m³·mol⁻¹	ChemAxon
Polarizability	77.51 Å³	ChemAxon
Number of Rings	3	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

HMDB0006565

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023975

KNApSAcK ID

Not Available

Chemspider ID

559072

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sialyl-Lewis X

METLIN ID

Not Available

PubChem Compound

643990

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Nashed, Mina A.; Musser, John H. A facile and regioselective synthesis of partially benzoylated 3',4'-O-isopropylidene-b-lactosides as standardized key intermediates for sialyl Lewis X (sLeX) analogs. Carbohydrate Research (1993), 250(2), C1-C4.

Showing chemical card for Sialyl-Lewis X (CFc000002813)

MOL for CFc000002813 (Sialyl-Lewis X)

3D MOL for CFc000002813 (Sialyl-Lewis X)

3D SDF for CFc000002813 (Sialyl-Lewis X)

3D-SDF for CFc000002813 (Sialyl-Lewis X)

PDB for CFc000002813 (Sialyl-Lewis X)

3D PDB for CFc000002813 (Sialyl-Lewis X)

SMILES for CFc000002813 (Sialyl-Lewis X)

INCHI for CFc000002813 (Sialyl-Lewis X)

Structure for CFc000002813 (Sialyl-Lewis X)

3D Structure for CFc000002813 (Sialyl-Lewis X)