N-(2,5-dimethoxy-4-methylphenyl)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalene-2-carboxamide

• ChemBase ID: 131534
• Molecular Formular: C28H32N2O9
• Molecular Mass: 540.56168
• Monoisotopic Mass: 540.21078061
• SMILES: Cc1cc(c(cc1OC)NC(=O)c1cc2ccccc2cc1O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)NC(=O)C)OC
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc3ccccc3cc2C(=O)Nc2cc(OC)c(cc2OC)C)[C@@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C28H32N2O9/c1-14-9-22(37-4)19(12-20(14)36-3)30-27(35)18-10-16-7-5-6-8-17(16)11-21(18)38-28-24(29-15(2)32)26(34)25(33)23(13-31)39-28/h5-12,23-26,28,31,33-34H,13H2,1-4H3,(H,29,32)(H,30,35)/t23-,24-,25-,26-,28-/m1/s1
• InChIKey: KNCCSKUQINPOFP-RDVFURSVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2,5-dimethoxy-4-methylphenyl)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalene-2-carboxamide
• IUPAC Traditional name: N-(2,5-dimethoxy-4-methylphenyl)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}naphthalene-2-carboxamide
• Synonyms: 2-Acetamido-2-deoxy-β-D-glucosidoxynaphthol AS-LC; Naphthol AS-LC N-acetyl-β-D-glucosaminide; N-Acetyl-β-D-glucosamine naphthol AS-LC

Database IDs

• CAS Number: 58225-96-0
• MDL Number: MFCD00057703
• PubChem SID: 162225812
• PubChem CID: 71308447

CALCULATED PROPERTIES

• Acid pKa: 10.505669
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 1.3930134
• LogD (pH = 7.4): 1.3926948
• Log P: 1.3930176
• Molar Refractivity: 141.2359 cm^3
• Polarizability: 55.72812 Å^3
• Polar Surface Area: 155.81 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

DETAILS

Sigma Aldrich - A8750

Substrates
An interesting substrate for the histochemical demonstration of N-acetylglucosaminidase and for possible quantitative assay systems.