2-{[(3S,4S,5R,6S)-3-acetamido-5-{[(2R,3S,4S,5R,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid

• ChemBase ID: 154557
• Molecular Formular: C19H32N2O13
• Molecular Mass: 496.46298
• Monoisotopic Mass: 496.19043909
• SMILES: CC(C(=O)O)O[C@@H]1[C@H]([C@@H](OC([C@H]1NC(=O)C)O)CO)O[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)CO)O)O)NC(=O)C
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@@H]([C@H]1O[C@H]1O[C@@H](CO)[C@@H]([C@H]([C@@H]1NC(=O)C)O)O)OC(C(=O)O)C)NC(=O)C
• InChI: InChI=1S/C19H32N2O13/c1-6(17(28)29)31-16-12(21-8(3)25)18(30)32-10(5-23)15(16)34-19-11(20-7(2)24)14(27)13(26)9(4-22)33-19/h6,9-16,18-19,22-23,26-27,30H,4-5H2,1-3H3,(H,20,24)(H,21,25)(H,28,29)/t6?,9-,10-,11-,12-,13-,14-,15-,16-,18?,19+/m0/s1
• InChIKey: WQKIVDUWFNRJHE-VFCBVHBBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(3S,4S,5R,6S)-3-acetamido-5-{[(2R,3S,4S,5R,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
• IUPAC Traditional name: 2-{[(3S,4S,5R,6S)-3-acetamido-5-{[(2R,3S,4S,5R,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
• Synonyms: β-GlcNAc-(1→4)-MurNAc; N-Acetyl-4-O-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-muramic acid

Database IDs

• CAS Number: 67068-85-3
• PubChem SID: 162248695
• PubChem CID: 71311901

CALCULATED PROPERTIES

• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): -6.64032
• LogD (pH = 7.4): -7.9824705
• Log P: -4.589571
• Molar Refractivity: 105.869 cm^3
• Polarizability: 43.66624 Å^3
• Polar Surface Area: 233.57 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false
• Acid pKa: 3.4384646

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

Product Information

• Purity: ≥97.0% (TLC)
• Empirical Formula (Hill Notation): C19H32N2O13

DETAILS

Sigma Aldrich - 57456

Other Notes
Bacterial cell wall muramyl disaccharide