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

• ChemBase ID: 164044
• Molecular Formular: C24H41N3O16
• Molecular Mass: 627.59284
• Monoisotopic Mass: 627.24868225
• SMILES: C1([C@@H]([C@@H](C([C@@H](O1)O)NC(=O)C)O)O[C@H]1C([C@H]([C@H](C(O1)CO)O[C@H]1C([C@H]([C@@H](C(O1)CO)O)O)NC(=O)C)O)NC(=O)C)CO
• Canonical SMILES: OCC1O[C@@H](O[C@H]2C(CO)O[C@H](C([C@H]2O)NC(=O)C)O)C([C@H]([C@H]1O[C@@H]1OC(CO)[C@H]([C@@H](C1NC(=O)C)O)O)O)NC(=O)C
• InChI: InChI=1S/C24H41N3O16/c1-7(31)25-13-18(36)20(11(5-29)39-22(13)38)42-24-15(27-9(3)33)19(37)21(12(6-30)41-24)43-23-14(26-8(2)32)17(35)16(34)10(4-28)40-23/h10-24,28-30,34-38H,4-6H2,1-3H3,(H,25,31)(H,26,32)(H,27,33)/t10?,11?,12?,13?,14?,15?,16-,17+,18+,19+,20+,21+,22-,23+,24+/m1/s1
• InChIKey: WZZVUHWLNMNWLW-PGHSOFRXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,4S,5R)-5-{[(2S,4S,5R)-3-acetamido-5-{[(2S,4S,5S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,4S,5R)-5-{[(2S,4S,5R)-3-acetamido-5-{[(2S,4S,5S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: α-Chitin; β-Chitin; γ-Chitin; Chitin, Practical Grade; Poly-(1-4)-β-N-acetyl-D-glucosamine; C 7170; N-Acetylchitan; Chitin Tc-L; ChitoRem SC 20; ChitoRem SC 80; Clandosan; Kimica Chitin F; Kimitsu Chitin; North Chitin CG 2; Regitex FA; SEC 1

Database IDs

• CAS Number: 1398-61-4
• PubChem SID: 162258179
• PubChem CID: 70824173

CALCULATED PROPERTIES

• Acid pKa: 11.40841
• H Acceptors: 16
• H Donor: 11
• LogD (pH = 5.5): -7.3383164
• LogD (pH = 7.4): -7.3383565
• Log P: -7.338316
• Molar Refractivity: 134.0539 cm^3
• Polarizability: 55.52393 Å^3
• Polar Surface Area: 295.29 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Insoluble in most solvents
• Apperance: Pale Yellow Solid
• Melting Point: >300°C (dec.)

Safety Information

• Storage Condition: Room Temp

DETAILS

Toronto Research Chemicals - C300800

A naturally occuring fibre found in the shells of shellfish. Used for the analysis of Chitinase.

REFERENCES

• Skujins, J.J., et al.: Arch. Biochem. Biophys., 111, 358 (1965).