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

• ChemBase ID: 133136
• Molecular Formular: C20H28N2O13
• Molecular Mass: 504.44192
• Monoisotopic Mass: 504.15913897
• SMILES: CC(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@@H]1Oc1ccc(cc1)[N+](=O)[O-])CO)O)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: OC[C@H]1O[C@H](Oc2ccc(cc2)[N+](=O)[O-])[C@@H]([C@H]([C@H]1O)O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)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)/t11-,12-,13-,14+,15+,16+,17-,18-,19+,20+/m1/s1
• InChIKey: INMOOBMAIAWVBW-UVFFFCKLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• Synonyms: 4-Nitrophenyl 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside; PNP Gal-β1,3-GalNAc; p-Nitrophenyl galacto-N-bioside; 4-Nitrophenyl 2-(Acetylamino)-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranoside; Gal1-β-3GalNAc-α-PNP; 4-Nitrophenyl 2-(Acetamido)-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranoside

Database IDs

• CAS Number: 59837-14-8
• MDL Number: MFCD00064051
• PubChem SID: 24897614; 162227413
• PubChem CID: 11168041

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

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: >225°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - N501000

Acetylgalactosaminidase sequence substrate Clostridium Bifidobacterium.

REFERENCES

• Medina, M. et al.: Cancer Res. 59,1061-1070, (1999)