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

• ChemBase ID: 105034
• Molecular Formular: C27H43N5O16
• Molecular Mass: 693.65422
• Monoisotopic Mass: 693.27048032
• SMILES: O=C(N)[C@H](NC(=O)[C@@H](NC(=O)[C@H](O[C@H]1[C@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2NC(=O)C)CO)[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[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1NC(=O)C)O)O)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/C27H43N5O16/c1-9(24(42)32-13(23(28)41)5-6-16(37)38)29-25(43)10(2)45-22-18(31-12(4)36)26(44)46-15(8-34)21(22)48-27-17(30-11(3)35)20(40)19(39)14(7-33)47-27/h9-10,13-15,17-22,27,33-34,39-40H,5-8H2,1-4H3,(H2,28,41)(H,29,43)(H,30,35)(H,31,36)(H,32,42)(H,37,38)/t9-,10+,13+,14+,15+,17+,18+,19+,20+,21+,22+,27-/m0/s1
• InChIKey: TXDCMFWLNAFPJK-URUMTOJBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-carbamoyl-4-[(2S)-2-[(2R)-2-{[(3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)-2-oxooxan-4-yl]oxy}propanamido]propanamido]butanoic acid
• IUPAC Traditional name: (4R)-4-carbamoyl-4-[(2S)-2-[(2R)-2-{[(3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)-2-oxooxan-4-yl]oxy}propanamido]propanamido]butanoic acid
• Synonyms: GMDP; N-ACETYL-D-GLUCOSAMINYL-β-(1→4)-N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE

Database IDs

• CAS Number: 70280-03-4
• PubChem SID: 162092084
• PubChem CID: 71299714

CALCULATED PROPERTIES

• Acid pKa: 4.0531354
• H Acceptors: 15
• H Donor: 10
• LogD (pH = 5.5): -8.093976
• LogD (pH = 7.4): -9.7632885
• Log P: -6.6354365
• Molar Refractivity: 151.9318 cm^3
• Polarizability: 61.631413 Å^3
• Polar Surface Area: 331.7 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C, Desiccate, Protect from light
• RTECS: MA2275230

Product Information

• Purity: 98%

DETAILS

MP Biomedicals - 02158221

Purity: 98%
Lyophilized
A novel synthetic analog of bacterial cell wall glycopeptide which acts as a modulator of humoral and cellular immunity reactions. Possesses immunoadjuvant and protective activity against bacterial and viral (including tumorigenic) infections. Differs from well-known muramyl peptides in that it contains GlcNAC attached to muramic acid via the β-(1𔾸) glycosidic bond.
Soluble in H₂ O, EtOH, MeOH, DMF, and physiological saline (1g/ml)

REFERENCES

• Campbell, M.J., et al., J. Immunology , 145 : 1029, (1990).
• Balitsky, K.P., et al., Int. J. Immunopharmacol. , 11 : 429, (1989).