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

• ChemBase ID: 169890
• Molecular Formular: C25H45N3O16
• Molecular Mass: 643.6353
• Monoisotopic Mass: 643.27998238
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)O[C@H]1[C@@H]([C@@H](CO[C@H]1CO)NC(=O)C)O)NC(=O)C)O)O.[C@@H]1([C@@H]([C@@H](C(O[C@H]1CO)O)NC(=O)C)O)OC
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@H]([C@@H]1OC)O)NC(=O)C.OC[C@@H]1OC[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/C16H28N2O10.C9H17NO6/c1-6(21)17-8-5-26-10(4-20)15(12(8)23)28-16-11(18-7(2)22)14(25)13(24)9(3-19)27-16;1-4(12)10-6-7(13)8(15-2)5(3-11)16-9(6)14/h8-16,19-20,23-25H,3-5H2,1-2H3,(H,17,21)(H,18,22);5-9,11,13-14H,3H2,1-2H3,(H,10,12)/t8-,9+,10+,11+,12+,13+,14+,15+,16-;5-,6-,7-,8-,9?/m01/s1
• InChIKey: NCXHGVZRWJLPFN-PFWVEFDXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide; N-[(3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide; N-[(3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-3-yl]acetamide
• Synonyms: GlcNAc1-b-4-GlcNAc1-b-4-GlcNAc1-b-4GlcNAc1-b-4GlcNAc1-b-4GlcNAc; N-acetylchitohexaose; N,N',N'',N''',N'''',N'''''-Hexaacetylchitohexaose

Database IDs

• CAS Number: 38854-46-5
• PubChem SID: 162264022
• PubChem CID: 71317212

CALCULATED PROPERTIES

• Acid pKa: 12.143544
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -4.9152217
• LogD (pH = 7.4): -4.9152284
• Log P: -4.915221
• Molar Refractivity: 89.5094 cm^3
• Polarizability: 36.75412 Å^3
• Polar Surface Area: 187.04 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: >213°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H290750

Studied for anti-tumor effects.

REFERENCES

• Suzuki, K., et al.: Carbohydrate Research, 151, 403 (1986)