[(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(2R,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-4-yl]oxy}oxan-2-yl]methyl acetate

• ChemBase ID: 175300
• Molecular Formular: C28H36N2O17
• Molecular Mass: 672.58864
• Monoisotopic Mass: 672.2013977
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)O[C@H]1[C@H]([C@@H](O[C@@H]([C@H]1NC(=O)C)Oc1ccc(cc1)[N+](=O)[O-])CO)O)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: OC[C@@H]1O[C@H](Oc2ccc(cc2)[N+](=O)[O-])[C@H]([C@H]([C@H]1O)O[C@@H]1O[C@@H](COC(=O)C)[C@@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C28H36N2O17/c1-12(32)29-21-24(22(37)19(10-31)45-27(21)44-18-8-6-17(7-9-18)30(38)39)47-28-26(43-16(5)36)25(42-15(4)35)23(41-14(3)34)20(46-28)11-40-13(2)33/h6-9,19-28,31,37H,10-11H2,1-5H3,(H,29,32)/t19-,20-,21-,22+,23+,24-,25+,26-,27+,28+/m1/s1
• InChIKey: NULURJYXRHZLHJ-LWAHQVHWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(2R,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-4-yl]oxy}oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(2R,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-4-yl]oxy}oxan-2-yl]methyl acetate
• Synonyms: 4-Nitrophenyl 2-(Acetylamino)-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside; p-Nitrophenyl 2-Acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside

Database IDs

• CAS Number: 59837-13-7
• PubChem SID: 164231210
• PubChem CID: 71307199

CALCULATED PROPERTIES

• Acid pKa: 11.683737
• H Acceptors: 13
• H Donor: 3
• LogD (pH = 5.5): -0.9527731
• LogD (pH = 7.4): -0.95279276
• Log P: -0.9527726
• Molar Refractivity: 147.6286 cm^3
• Polarizability: 60.138397 Å^3
• Polar Surface Area: 257.5 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Crystalline Solid
• Melting Point: 153-155°C dec.

REFERENCES

• Medina, M. et al.: Cancer Res. 59,1061-1070, (1999)