(2S,4S,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-5-acetamido-2-(hydroxymethyl)-6-methoxy-4-{[(2S,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-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 177705
• Molecular Formular: C32H54N2O23
• Molecular Mass: 834.77076
• Monoisotopic Mass: 834.311736
• SMILES: [C@@H]1(C([C@@H](C[C@](O1)(O[C@H]1[C@H]([C@@H](O[C@H]([C@H]1O)O[C@H]1[C@@H]([C@@H]([C@@H](O[C@H]1CO)OC)NC(=O)C)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C)O)O)O)CO)O)C(=O)O)O)NC(=O)C)[C@@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@](O[C@@H]2[C@H](O)[C@@H](O[C@H]([C@@H]2O)CO)O[C@@H]2[C@H](CO)O[C@H]([C@H]([C@H]2O[C@@H]2O[C@@H](C)[C@H]([C@@H]([C@@H]2O)O)O)NC(=O)C)OC)(C[C@H](C1NC(=O)C)O)C(=O)O)O)O
• InChI: InChI=1S/C32H54N2O23/c1-9-18(42)21(45)22(46)29(51-9)55-26-17(34-11(3)39)28(50-4)53-15(8-37)24(26)54-30-23(47)27(20(44)14(7-36)52-30)57-32(31(48)49)5-12(40)16(33-10(2)38)25(56-32)19(43)13(41)6-35/h9,12-30,35-37,40-47H,5-8H2,1-4H3,(H,33,38)(H,34,39)(H,48,49)/t9-,12-,13+,14+,15+,16?,17+,18+,19+,20-,21+,22-,23+,24+,25+,26+,27-,28+,29-,30-,32-/m0/s1
• InChIKey: BEVDUZXAAXDNBM-YSRGTLPVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-5-acetamido-2-(hydroxymethyl)-6-methoxy-4-{[(2S,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-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,4S,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-5-acetamido-2-(hydroxymethyl)-6-methoxy-4-{[(2S,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-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: [Neu5Ac2-α-3Gal1-b-4[Fuc1-α-3]GlcNAc1-O-b-Me]; [Methyl O-[5-Acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic Acid)-2-α-3-O-β-D-galactopyranosyl]-1-b-4-O-[(α-L-fucopyranosyl)-1-α-3]-2-acetamido-2-deoxy-β-D-glucopyranoside]; Sialyl Lewis X, Methyl Glycoside

Database IDs

• CAS Number: 141612-87-5
• PubChem SID: 164233615
• PubChem CID: 71752164

CALCULATED PROPERTIES

• Acid pKa: 2.8378649
• H Acceptors: 23
• H Donor: 14
• LogD (pH = 5.5): -10.082249
• LogD (pH = 7.4): -10.965422
• Log P: -7.474443
• Molar Refractivity: 175.3301 cm^3
• Polarizability: 73.093025 Å^3
• Polar Surface Area: 391.87 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; water
• Apperance: Amorphous White Solid

Safety Information

• Storage Condition: -20°C Freezer

REFERENCES

• Fukushima, K., et al.: Cancer Research, 44, 5279 (1984)
• Zein, N., et al.: Science, 240, 1198 (1984)
• Phillips, M.L., et al.: Science, 250, 1130 (1984)
• Walz, G., et al.: P.N.A.S. U.S.A., 88, 6224 (1984)
• Walker, S., et al.: P.N.A.S. U.S.A., 89, 4608 (19