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

• ChemBase ID: 133494
• Molecular Formular: C12H21N3O8
• Molecular Mass: 335.31044
• Monoisotopic Mass: 335.13286465
• SMILES: CC(=O)NC1C(C(C(OC1NC(=O)CC(C(=O)O)N)CO)O)O
• Canonical SMILES: OCC1OC(NC(=O)CC(C(=O)O)N)C(C(C1O)O)NC(=O)C
• InChI: InChI=1S/C12H21N3O8/c1-4(17)14-8-10(20)9(19)6(3-16)23-11(8)15-7(18)2-5(13)12(21)22/h5-6,8-11,16,19-20H,2-3,13H2,1H3,(H,14,17)(H,15,18)(H,21,22)
• InChIKey: YTTRPBWEMMPYSW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-{[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]carbamoyl}propanoic acid
• IUPAC Traditional name: 2-amino-3-{[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]carbamoyl}propanoic acid
• Synonyms: β-D-GlcNAc-(1→N)-Asn; 2-Acetamido-1-β-(L-aspartamido)-1,2-dideoxy-D-glucose; L-Asparagine, N-[2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]; 2-Acetamido-1-N-(β-L-aspartyl)-2-deoxy-β-D-glucopyranosylamine

Database IDs

• CAS Number: 2776-93-4
• MDL Number: MFCD00056071
• PubChem SID: 24891128; 162227771
• PubChem CID: 184

CALCULATED PROPERTIES

• Acid pKa: 1.5762091
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -6.7678638
• LogD (pH = 7.4): -6.8037004
• Log P: -6.767629
• Molar Refractivity: 72.015 cm^3
• Polarizability: 29.508318 Å^3
• Polar Surface Area: 191.44 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%

DETAILS

Sigma Aldrich - A6681

Application
n-acetylglucosaminylasparagine [2-Acetamido-1-N-(β-L-aspartyl)-2-deoxy-β-D-glucopyranosylamine] may be useful in studies on Aspartylglycosaminuria.