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

• ChemBase ID: 132030
• Molecular Formular: C20H28N2O13
• Molecular Mass: 504.44192
• Monoisotopic Mass: 504.15913897
• SMILES: CC(=O)NC1C(C(C(OC1Oc1ccc(cc1)[N+](=O)[O-])CO)O)OC1C(C(C(C(O1)CO)O)O)O
• Canonical SMILES: OCC1OC(Oc2ccc(cc2)[N+](=O)[O-])C(C(C1O)OC1OC(CO)C(C(C1O)O)O)NC(=O)C
• InChI: InChI=1S/C20H28N2O13/c1-8(25)21-13-18(35-20-17(29)16(28)14(26)11(6-23)34-20)15(27)12(7-24)33-19(13)32-10-4-2-9(3-5-10)22(30)31/h2-5,11-20,23-24,26-29H,6-7H2,1H3,(H,21,25)
• InChIKey: INMOOBMAIAWVBW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: N-[5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• Synonyms: p-Nitrophenyl lacto-N-bioside; 4-Nitrophenyl 2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-β-D-glucopyranoside

Database IDs

• CAS Number: 57467-13-7
• MDL Number: MFCD00037620
• PubChem SID: 162226307; 24897738
• PubChem CID: 4568966

CALCULATED PROPERTIES

• Acid pKa: 11.623808
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -2.7172747
• LogD (pH = 7.4): -2.717298
• Log P: -2.7172742
• Molar Refractivity: 111.0226 cm^3
• Polarizability: 44.714172 Å^3
• Polar Surface Area: 233.22 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
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - N5513

Substrates
Useful as a chromophoric marker substrate for Lewis blood group-specific fucosyltransferases.