5-acetamido-2-{[2-({2-acetamido-5,6-dihydroxy-1-oxo-4-[(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-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

• ChemBase ID: 133248
• Molecular Formular: C31H52N2O23
• Molecular Mass: 820.74418
• Monoisotopic Mass: 820.29608593
• SMILES: CC1C(C(C(C(O1)OC(C(CO)O)C(C(C=O)NC(=O)C)OC1C(C(C(C(O1)CO)O)OC1(CC(C(C(O1)C(C(CO)O)O)NC(=O)C)O)C(=O)O)O)O)O)O
• Canonical SMILES: O=CC(C(C(C(CO)O)OC1OC(C)C(C(C1O)O)O)OC1OC(CO)C(C(C1O)OC1(CC(O)C(C(O1)C(C(CO)O)O)NC(=O)C)C(=O)O)O)NC(=O)C
• InChI: InChI=1S/C31H52N2O23/c1-9-18(43)21(46)22(47)28(51-9)54-25(15(42)7-36)24(12(5-34)32-10(2)38)53-29-23(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)
• InChIKey: INZOTETZQBPBCE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-acetamido-2-{[2-({2-acetamido-5,6-dihydroxy-1-oxo-4-[(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-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
• IUPAC Traditional name: 5-acetamido-2-{[2-({2-acetamido-5,6-dihydroxy-1-oxo-4-[(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-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
• Synonyms: α-NeuNAc-(2→3)-β-D-Gal-(1→3)-(α-L-Fuc-[1→4])-D-GlcNAc; 3′-SLea; 3′-Sialyl-Lewis-a tetrasaccharide

Database IDs

• CAS Number: 92448-22-1
• MDL Number: MFCD00214218
• PubChem SID: 24899518; 162227525
• PubChem CID: 3349566

CALCULATED PROPERTIES

• Acid pKa: 2.8881383
• H Acceptors: 23
• H Donor: 15
• LogD (pH = 5.5): -11.316751
• LogD (pH = 7.4): -12.239903
• Log P: -8.753391
• Molar Refractivity: 172.0011 cm^3
• Polarizability: 71.32387 Å^3
• Polar Surface Area: 410.71 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - S2279

Biochem/physiol Actions
Antigen which supports E-, L-, and P-selectin-dependent adhesion.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. S2279.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.