N-[4,5-dihydroxy-6-(hydroxymethyl)-2-[(3,4,5-trihydroxy-6-methoxyoxan-2-yl)methoxy]oxan-3-yl]acetamide

• ChemBase ID: 131794
• Molecular Formular: C15H27NO11
• Molecular Mass: 397.37498
• Monoisotopic Mass: 397.15841069
• SMILES: CC(=O)NC1C(C(C(OC1OCC1C(C(C(C(O1)OC)O)O)O)CO)O)O
• Canonical SMILES: COC1OC(COC2OC(CO)C(C(C2NC(=O)C)O)O)C(C(C1O)O)O
• InChI: InChI=1S/C15H27NO11/c1-5(18)16-8-11(21)9(19)6(3-17)26-14(8)25-4-7-10(20)12(22)13(23)15(24-2)27-7/h6-15,17,19-23H,3-4H2,1-2H3,(H,16,18)
• InChIKey: UXYSKKBVNODRDW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[4,5-dihydroxy-6-(hydroxymethyl)-2-[(3,4,5-trihydroxy-6-methoxyoxan-2-yl)methoxy]oxan-3-yl]acetamide
• IUPAC Traditional name: N-[4,5-dihydroxy-6-(hydroxymethyl)-2-[(3,4,5-trihydroxy-6-methoxyoxan-2-yl)methoxy]oxan-3-yl]acetamide
• Synonyms: β-D-GlcNAc-(1→6)-α-D-Man-1→OMe; Methyl 6-O-(N-acetyl-β-D-glucosaminyl)-α-D-mannopyranoside

Database IDs

• CAS Number: 80264-88-6
• MDL Number: MFCD00057915
• PubChem SID: 24896568; 162226071
• PubChem CID: 4183957

CALCULATED PROPERTIES

• Acid pKa: 11.885333
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -4.348284
• LogD (pH = 7.4): -4.348297
• Log P: -4.348284
• Molar Refractivity: 84.1892 cm^3
• Polarizability: 35.078526 Å^3
• Polar Surface Area: 187.4 Å^2
• Rotatable Bonds: 6
• 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

DETAILS

Sigma Aldrich - M0774

Application
A model compound for the study of proteoglycans by NMR.1,2
Biochem/physiol Actions
Mitochondrial ATP-dependent protease substrate