N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 155524
• Molecular Formular: C22H31N3O13
• Molecular Mass: 545.49384
• Monoisotopic Mass: 545.18568807
• SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)NC(=O)C)Oc1ccc(cc1)[N+](=O)[O-])CO)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2)[N+](=O)[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)NC(=O)C
• InChI: InChI=1S/C22H31N3O13/c1-9(28)23-15-18(31)17(30)13(7-26)36-22(15)38-20-14(8-27)37-21(16(19(20)32)24-10(2)29)35-12-5-3-11(4-6-12)25(33)34/h3-6,13-22,26-27,30-32H,7-8H2,1-2H3,(H,23,28)(H,24,29)/t13-,14-,15-,16-,17-,18-,19-,20-,21-,22+/m1/s1
• InChIKey: HWBFEVWOQMUQIE-MVEDJEFUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: 4-Nitrophenyl N,N′-diacetyl-β-D-chitobioside; 4-Nitrophenyl 2-(Acetylamino)-4-O-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-2-deoxy-β-D-glucopyranoside; p-Nitrophenyl-N,N'-diacetylchitobioside; 4-Nitrophenyl N,N-Diacetyl-β-D-chitobioside

Database IDs

• CAS Number: 7284-16-4
• MDL Number: MFCD00133738
• Beilstein Number: 1445509
• PubChem SID: 162249662; 24897770
• PubChem CID: 10907699

CALCULATED PROPERTIES

• Rotatable Bonds: 9
• Lipinski's Rule of Five: false
• Acid pKa: 11.61962
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -3.00531
• LogD (pH = 7.4): -3.005333
• Log P: -3.0053093
• Molar Refractivity: 122.1239 cm^3
• Polarizability: 48.971577 Å^3
• Polar Surface Area: 242.09 Å^2

PROPERTIES

Physical Property

• Solubility: DMF: soluble25 mg/mL, clear, light yellow; DMSO
• Apperance: Off-White Solid
• Melting Point: 211-212°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99% (TLC); ≥99.0% (TLC)
• Impurities: ≤5% water
• Empirical Formula (Hill Notation): C22H31N3O13

DETAILS

Sigma Aldrich - 73623

Other Notes
Substrate for the assay of chitobiosidase1