N-[(3R,4R,5R,6R)-2,4,5-trihydroxy-6-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]acetamide

• ChemBase ID: 158893
• Molecular Formular: C14H25NO11
• Molecular Mass: 383.3484
• Monoisotopic Mass: 383.14276063
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)OC[C@H]1[C@@H]([C@@H]([C@@H](C(O1)O)NC(=O)C)O)O)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](OC[C@@H]2OC(O)[C@H]([C@H]([C@H]2O)O)NC(=O)C)[C@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C14H25NO11/c1-4(17)15-7-10(20)9(19)6(25-13(7)23)3-24-14-12(22)11(21)8(18)5(2-16)26-14/h5-14,16,18-23H,2-3H2,1H3,(H,15,17)/t5-,6-,7-,8+,9+,10-,11+,12-,13?,14-/m1/s1
• InChIKey: ACKXCNXSQYSCQN-UUHITYSKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5R,6R)-2,4,5-trihydroxy-6-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(3R,4R,5R,6R)-2,4,5-trihydroxy-6-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]acetamide
• Synonyms: 2-(Acetylamino)-2-deoxy-6-O-β-D-galactopyranosyl-D-galactopyranose; Gal1-β-6GalNAc; 2-Acetamido-2-deoxy-6-O-(β-D-galactopyranosyl)-D-galactopyranose

Database IDs

• CAS Number: 209977-51-5
• PubChem SID: 162253028
• PubChem CID: 21126521

CALCULATED PROPERTIES

• Acid pKa: 11.46143
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.9914107
• LogD (pH = 7.4): -4.9914465
• Log P: -4.9914103
• Molar Refractivity: 79.438 cm^3
• Polarizability: 33.212086 Å^3
• Polar Surface Area: 198.4 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: White Crystalline Solid
• Melting Point: 159-160°C dec.

DETAILS

Toronto Research Chemicals - A152500

Occurs as part of a glycoprotein isolated from the cervical mucus of the Bonnet monkey.

REFERENCES

• Hatcher, V.B., et al.: Biochemistry, 16, 1815 (1977)