N-[(2R,3R,4S,5R)-4-{[(2S,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5,6-trihydroxy-1-oxohexan-2-yl]acetamide

• ChemBase ID: 106070
• Molecular Formular: C24H41N3O16
• Molecular Mass: 627.59284
• Monoisotopic Mass: 627.24868225
• SMILES: O=C[C@H](NC(=O)C)[C@@H](O)[C@H](O[C@@H]1O[C@@H]([C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(=O)C)[C@H](O)[C@H]1NC(=O)C)CO)[C@H](O)CO
• Canonical SMILES: OC[C@H]([C@H]([C@@H]([C@@H](NC(=O)C)C=O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1NC(=O)C)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1NC(=O)C)O)O)O
• InChI: InChI=1S/C24H41N3O16/c1-8(32)25-11(4-28)17(36)21(12(35)5-29)42-24-16(27-10(3)34)20(39)22(14(7-31)41-24)43-23-15(26-9(2)33)19(38)18(37)13(6-30)40-23/h4,11-24,29-31,35-39H,5-7H2,1-3H3,(H,25,32)(H,26,33)(H,27,34)/t11-,12+,13+,14+,15+,16+,17+,18+,19+,20+,21+,22+,23-,24-/m0/s1
• InChIKey: LRDDKCYRFNJZBX-WHFMPQCRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4S,5R)-4-{[(2S,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5,6-trihydroxy-1-oxohexan-2-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4S,5R)-4-{[(2S,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5,6-trihydroxy-1-oxohexan-2-yl]acetamide
• Synonyms: O-[2-Acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)]-O-[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)]-2-acetamido-2-deoxy-D-glucopyranose; N,N′,N′′-Triacetylchitotriose; Chitotriose; N,N',N'-TRIACETYLCHITOTRIOSE

Database IDs

• CAS Number: 38864-21-0
• MDL Number: MFCD00136047
• Beilstein Number: 75249
• PubChem SID: 162092868; 24900018
• PubChem CID: 123774

CALCULATED PROPERTIES

• Acid pKa: 11.340471
• H Acceptors: 16
• H Donor: 11
• LogD (pH = 5.5): -7.9741383
• LogD (pH = 7.4): -7.9741845
• Log P: -7.9741373
• Molar Refractivity: 135.4761 cm^3
• Polarizability: 55.621826 Å^3
• Polar Surface Area: 303.13 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear to slightly hazy, colorless to faintly yellow

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ~95% (HPLC); ≥95% (HPLC)
• Impurities: ≤6% water
• Empirical Formula (Hill Notation): C24H41N3O16

DETAILS

MP Biomedicals - 02198906

Possesses immunostimulating and anti-tumor activities.

Sigma Aldrich - T2144

Preparation Note
Prepared by the method of Barker, S.A., et al., J. Chem. Soc., 2218 (1958).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T2144.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 90251

Other Notes
Studies on a chitooligosaccharide-specific lectin1

REFERENCES

• Gorbach VI, et al, Carbohyd.Res. , 260(1) : 73-82, Jul 4, (1994).