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

• ChemBase ID: 128472
• Molecular Formular: C9H17NO7
• Molecular Mass: 251.23378
• Monoisotopic Mass: 251.10050189
• SMILES: O=C(O)[C@H](O[C@H]1[C@H](O)[C@H](OC(O)[C@@H]1N)CO)C
• Canonical SMILES: OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1O)O[C@@H](C(=O)O)C)N
• InChI: InChI=1S/C9H17NO7/c1-3(8(13)14)16-7-5(10)9(15)17-4(2-11)6(7)12/h3-7,9,11-12,15H,2,10H2,1H3,(H,13,14)/t3-,4-,5-,6-,7-,9?/m1/s1
• InChIKey: MSFSPUZXLOGKHJ-PGYHGBPZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(3R,4R,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
• IUPAC Systematic name: 2-{[3-Amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
• IUPAC Traditional name: muramic acid
• Synonyms: (R)-2-Amino-3-O-(1-carboxyethyl)-2-deoxy-D-glucose; Muramic acid

Database IDs

• CAS Number: 1114-41-6
• EC Number: 214-214-9
• Beilstein Number: 2334586
• PubChem SID: 162222779
• PubChem CID: 441038
• CHEBI ID: 7027
• Chemspider ID: 7992151
• KEGG ID: C06470
• Wikipedia Title: Muramic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.328594
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -4.6142592
• LogD (pH = 7.4): -4.6818953
• Log P: -4.614715
• Molar Refractivity: 52.9106 cm^3
• Polarizability: 22.164417 Å^3
• Polar Surface Area: 142.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol; Water
• Apperance: White to Light Yellow Solid
• Melting Point: 135-136°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M800000

Amino sugar found (as the N-acetyl derivative) in peptidoglycan, the main skeletal component of the bacterial cell wall. The N-acetyl derivative of muramic acid is an amino sugar that constitutes the peptidoglycan bacterial cell wall of Gram negative and

REFERENCES

• Stout, J., et al.: Soil Biochem., 5, 1 (1981)
• Chantigny, M., et al.: Soil Biol. Biochem., 32, 1561 (1981)
• Martens, D., et al.: J. Environ. Qual., 29, 723 (1981)