N-[(2S,3R,4R,5S,6R)-2-[(5-amino-4-oxo-3,4-dihydrophthalazin-1-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 160433
• Molecular Formular: C16H20N4O7
• Molecular Mass: 380.3526
• Monoisotopic Mass: 380.133199
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)Oc1n[nH]c(=O)c2c1cccc2N)NC(=O)C)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2n[nH]c(=O)c3c2cccc3N)[C@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C16H20N4O7/c1-6(22)18-11-13(24)12(23)9(5-21)26-16(11)27-15-7-3-2-4-8(17)10(7)14(25)19-20-15/h2-4,9,11-13,16,21,23-24H,5,17H2,1H3,(H,18,22)(H,19,25)/t9-,11-,12-,13-,16+/m1/s1
• InChIKey: YLCXXNRWYKEOPP-CSTFGSAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-2-[(5-amino-4-oxo-3,4-dihydrophthalazin-1-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-2-[(5-amino-4-oxo-3H-phthalazin-1-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: LUM-NAG; 2-Aminophthalylhydrazido-N-acetyl-β-D-glucosaminide

Database IDs

• CAS Number: 128879-80-1
• PubChem SID: 162254568
• PubChem CID: 14629752

CALCULATED PROPERTIES

• Acid pKa: 10.990614
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -1.8331856
• LogD (pH = 7.4): -1.8332261
• Log P: -1.8331264
• Molar Refractivity: 91.3515 cm^3
• Polarizability: 34.851578 Å^3
• Polar Surface Area: 175.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 178-180°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A627700

A chemiluminogenic substrate for N-Acetyl-β-D-glucosamidase.

REFERENCES

• Sasamoto, K. et al.: Chem. Pharm. Bull., 38, 5, 1323 (1990)