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

• ChemBase ID: 128473
• Molecular Formular: C19H32N4O11
• Molecular Mass: 492.47758
• Monoisotopic Mass: 492.20675786
• SMILES: O=C(N)[C@H](NC(=O)[C@@H](NC(=O)[C@H](O[C@H]1[C@H](O)[C@H](OC(O)[C@@H]1NC(=O)C)CO)C)C)CCC(=O)O
• Canonical SMILES: OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1O)O[C@@H](C(=O)N[C@H](C(=O)N[C@@H](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)/t7-,8+,10+,11+,13+,14+,15+,19?/m0/s1
• InChIKey: BSOQXXWZTUDTEL-QAQREVAFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-carbamoyl-4-[(2S)-2-[(2R)-2-{[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanoic acid
• IUPAC Traditional name: muramyl dipeptide
• Synonyms: Acetylmuramyl-Alanyl-Isoglutamine; Muramyl dipeptide; Adjuvant Peptide; Muramyl dipeptide; N-Acetylmuramyl-L-alanyl-D-isoglutamine hydrate

Database IDs

• CAS Number: 53678-77-6
• EC Number: 258-696-9
• MDL Number: MFCD00077638
• Beilstein Number: 4220745
• PubChem SID: 24891464; 162222780
• PubChem CID: 11620162
• Chemspider ID: 9794910
• MeSH Name: Muramyl+dipeptide
• Wikipedia Title: Muramyl_dipeptide

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

• RTECS: MA2275260
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC)

DETAILS

Sigma Aldrich - A9519

Amino Acid Sequence
MurNAc-Ala-Agn
Biochem/physiol Actions
Enhances antigenicity of weak antigens, increasing antibody titer.