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

• ChemBase ID: 158868
• Molecular Formular: C12H21NO8
• Molecular Mass: 307.29704
• Monoisotopic Mass: 307.12671664
• SMILES: [C@@H]1([C@@H]([C@@H](C(O[C@H]1CO)O)NC(=O)C)O[C@H](C)C(=O)OC)O
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@H]([C@@H]1O)O[C@@H](C(=O)OC)C)NC(=O)C
• InChI: InChI=1S/C12H21NO8/c1-5(11(17)19-3)20-10-8(13-6(2)15)12(18)21-7(4-14)9(10)16/h5,7-10,12,14,16,18H,4H2,1-3H3,(H,13,15)/t5-,7-,8-,9-,10-,12?/m1/s1
• InChIKey: QQQLKKYLIRADTB-QQGRBGMQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R)-2-{[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoate
• IUPAC Traditional name: methyl (2R)-2-{[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoate
• Synonyms: N-Acetylmuramic Acid Methyl Ester; 2-(Acetylamino)-2-deoxy-3-O-(2-methoxy-1-methyl-2-oxoethyl)-d-Glucose; 2-Acetamido-3-O-(D-1-carboxyethyl)-2-deoxy-2-D-glucose Methyl Ester

Database IDs

• CAS Number: 99689-20-0
• PubChem SID: 162253003
• PubChem CID: 71312721

CALCULATED PROPERTIES

• Acid pKa: 11.613196
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.3848069
• LogD (pH = 7.4): -2.3848321
• Log P: -2.3848064
• Molar Refractivity: 67.1235 cm^3
• Polarizability: 27.637323 Å^3
• Polar Surface Area: 134.55 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 122-124°C

DETAILS

Toronto Research Chemicals - A148275

Acetyl derivative of Muramic acid.

REFERENCES

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