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

• ChemBase ID: 161384
• Molecular Formular: C26H33NO8
• Molecular Mass: 487.54212
• Monoisotopic Mass: 487.22061702
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O[C@H]1COCc1ccccc1)OCc1ccccc1)NC(=O)C)O[C@H](C)C(=O)OC)O
• Canonical SMILES: COC(=O)[C@H](O[C@H]1[C@H](O)[C@H](COCc2ccccc2)O[C@@H]([C@H]1NC(=O)C)OCc1ccccc1)C
• InChI: InChI=1S/C26H33NO8/c1-17(25(30)31-3)34-24-22(27-18(2)28)26(33-15-20-12-8-5-9-13-20)35-21(23(24)29)16-32-14-19-10-6-4-7-11-19/h4-13,17,21-24,26,29H,14-16H2,1-3H3,(H,27,28)/t17-,21-,22-,23-,24-,26+/m1/s1
• InChIKey: NSTACECEWGGFLK-IPIPSWHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R)-2-{[(2S,3R,4R,5S,6R)-2-(benzyloxy)-6-[(benzyloxy)methyl]-3-acetamido-5-hydroxyoxan-4-yl]oxy}propanoate
• IUPAC Traditional name: methyl (2R)-2-{[(2S,3R,4R,5S,6R)-2-(benzyloxy)-6-[(benzyloxy)methyl]-3-acetamido-5-hydroxyoxan-4-yl]oxy}propanoate
• Synonyms: N-Acetyl-1,6-bis-O-(phenylmethyl)-α-muramic Acid Methyl Ester; (R)-Phenylmethyl 2-(Acetylamino)-2-deoxy-3-O-(2-methoxy-1-methyl-2-oxoethyl)-6-O-(phenylmethyl)-α-D-glucopyranoside; Benzyl N-Acetyl-6-O-benzyl-α-D-muramic Acid Methyl Ester

Database IDs

• CAS Number: 107671-54-5
• PubChem SID: 162255519
• PubChem CID: 54128652

CALCULATED PROPERTIES

• Acid pKa: 12.379181
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 2.3503926
• LogD (pH = 7.4): 2.3503888
• Log P: 2.350393
• Molar Refractivity: 125.8511 cm^3
• Polarizability: 50.382866 Å^3
• Polar Surface Area: 112.55 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-White Solid
• Melting Point: 118-119°C

DETAILS

Toronto Research Chemicals - B223475

The N-acetyl derivative of muramic acid is an amino sugar found in peptidoglycan, the main skeletal component of both Gram positive and Gram negative bacterial cell wall.

REFERENCES

• J. Biol. Chem., 194, 885, 1952; Ann. NY Acad. Sci., 235, 29-51 (1974)
• J. Am. Chem. Soc., 28, 2983 (1963)