4-carbamoyl-4-[2-(2-{[3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido)propanamido]butanoic acid

• ChemBase ID: 105893
• Molecular Formular: C19H32N4O11
• Molecular Mass: 492.47758
• Monoisotopic Mass: 492.20675786
• SMILES: CC(NC(=O)C(C)OC1C(O)C(CO)OC(O)C1NC(=O)C)C(=O)NC(CCC(=O)O)C(=O)N
• Canonical SMILES: OCC1OC(O)C(C(C1O)OC(C(=O)NC(C(=O)NC(C(=O)N)CCC(=O)O)C)C)NC(=O)C
• InChI: InChI=1S/C19H32N4O11/c1-7(17(30)23-10(16(20)29)4-5-12(26)27)21-18(31)8(2)33-15-13(22-9(3)25)19(32)34-11(6-24)14(15)28/h7-8,10-11,13-15,19,24,28,32H,4-6H2,1-3H3,(H2,20,29)(H,21,31)(H,22,25)(H,23,30)(H,26,27)
• InChIKey: BSOQXXWZTUDTEL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-carbamoyl-4-[2-(2-{[3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido)propanamido]butanoic acid
• IUPAC Traditional name: 4-carbamoyl-4-[2-(2-{[3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido)propanamido]butanoic acid
• Synonyms: N-Acetylmuramyl-L-Ala-D-Isoglutamine; ADJUVANT PEPTIDE

Database IDs

• CAS Number: 53678-77-6
• EC Number: 258-696-9
• PubChem SID: 162092897
• PubChem CID: 4140922

CALCULATED PROPERTIES

• Acid pKa: 4.0531354
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -6.2223706
• LogD (pH = 7.4): -7.8916774
• Log P: -4.7638316
• Molar Refractivity: 109.5618 cm^3
• Polarizability: 44.097977 Å^3
• Polar Surface Area: 246.84 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C
• RTECS: MA2275260

DETAILS

MP Biomedicals - 02195011

Used in immunization to replace more complex proteins.

REFERENCES

• Ellouz, F., et al., Biochem. Biophys. Res. Commun. , 59 : 1317, (1974).
• Lefancier, P., et al., Int. J. Peptide Protein Res. , 9 : 249, (1977).
• Chedid, L. and Lederer, E., Biochem. Pharmac. , 27 : 2183, (1978).