methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromo(2,3,4,5,6-13C5)oxane-2-carboxylate

• ChemBase ID: 158966
• Molecular Formular: C13H17BrO9
• Molecular Mass: 403.12860903
• Monoisotopic Mass: 402.02572315
• SMILES: [13C@@H]1([13C@@H]([13C@@H]([13C@H](O[13C@H]1[13C](=O)OC)Br)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CO[13C](=O)[13C@@H]1O[13C@H](Br)[13C@H]([13C@H]([13C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C13H17BrO9/c1-5(15)20-8-9(21-6(2)16)11(13(18)19-4)23-12(14)10(8)22-7(3)17/h8-12H,1-4H3/t8-,9-,10+,11-,12-/m0/s1/i8+1,9+1,10+1,11+1,12+1,13+1
• InChIKey: GWTNLHGTLIBHHZ-JQNMFBIBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromo(2,3,4,5,6-^1^3C₅)oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromo(2,3,4,5,6-^1^3C₅)oxane-2-carboxylate
• Synonyms: 1-Bromo-1-deoxy-2,3,4-triacetate α-D-Glucopyranuronic-13C6 Acid Methyl Ester; Methyl (Tri-O-acetyl-α-D-glucopyranosyl Bromide)uronate-13C6; Methyl 2,3,4-Tri-O-acetyl-1-bromo-1-deoxy-α-D-glucopyranuranate-13C6; Methyl α-Acetobromo-glucuronate-13C6; Acetobromo-α-D-glucuronic Acid-13C6 Methyl Ester

Database IDs

• PubChem SID: 162253101
• PubChem CID: 71312758

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.38527408
• LogD (pH = 7.4): -0.38527408
• Log P: -0.38527408
• Molar Refractivity: 74.3686 cm^3
• Polarizability: 31.050533 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A162002

Antitumor agent.

REFERENCES

• Honda, T., et al.: J. Med. Chem., 31, 1295 (1988)