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

• ChemBase ID: 128501
• Molecular Formular: C11H19NO8
• Molecular Mass: 293.27046
• Monoisotopic Mass: 293.11106657
• SMILES: O=C(O)[C@H](O[C@H]1[C@H](O)[C@H](OC(O)[C@@H]1NC(=O)C)CO)C
• Canonical SMILES: OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1O)O[C@@H](C(=O)O)C)NC(=O)C
• InChI: InChI=1S/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11?/m1/s1
• InChIKey: MNLRQHMNZILYPY-MKFCKLDKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
• IUPAC Traditional name: N-acetylmuramic acid
• Synonyms: N-Acetylmuramic acid; 2-Acetamido-3-O-(D-1-carboxyethyl)-2-deoxy-2-D-glucose; N-Acetylmuramic Acid

Database IDs

• CAS Number: 10597-89-4
• PubChem SID: 162222808
• PubChem CID: 5462244
• Chemspider ID: 4575341
• Wikipedia Title: N-Acetylmuramic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.5814805
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -4.4439344
• LogD (pH = 7.4): -5.8801446
• Log P: -2.5307004
• Molar Refractivity: 62.3544 cm^3
• Polarizability: 25.604103 Å^3
• Polar Surface Area: 145.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A148265

Acetyl derivative of Muramic acid.

REFERENCES

• Carroll, P. M., et al.: Nature, 197, 694 (1963)