(2S,3S,4S,5R,6S)-6-(4-{[13-chloro-10-(2,6-difluorophenyl)-3,5,9-triazatricyclo[9.4.0.02,7]pentadeca-1(11),2(7),3,5,9,12,14-heptaen-4-yl]amino}benzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 174431
• Molecular Formular: C31H23ClF2N4O8
• Molecular Mass: 652.9861264
• Monoisotopic Mass: 652.11724784
• SMILES: c12c(C(=NCc3c1nc(nc3)Nc1ccc(cc1)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)c1c(cccc1F)F)cc(cc2)Cl
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC(=O)c2ccc(cc2)Nc2ncc3c(n2)c2ccc(cc2C(=NC3)c2c(F)cccc2F)Cl)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C31H23ClF2N4O8/c32-15-6-9-17-18(10-15)23(21-19(33)2-1-3-20(21)34)35-11-14-12-36-31(38-22(14)17)37-16-7-4-13(5-8-16)29(44)46-30-26(41)24(39)25(40)27(45-30)28(42)43/h1-10,12,24-27,30,39-41H,11H2,(H,42,43)(H,36,37,38)/t24-,25-,26+,27-,30-/m0/s1
• InChIKey: WGEBLJONXRHDSS-MOWXUVRXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-(4-{[13-chloro-10-(2,6-difluorophenyl)-3,5,9-triazatricyclo[9.4.0.0^2,^7]pentadeca-1(11),2(7),3,5,9,12,14-heptaen-4-yl]amino}benzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-(4-{[13-chloro-10-(2,6-difluorophenyl)-3,5,9-triazatricyclo[9.4.0.0^2,^7]pentadeca-1(11),2(7),3,5,9,12,14-heptaen-4-yl]amino}benzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[4-[[9-Chloro-7-(2,6-difluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino]benzoate] β-D-Glucopyranuronic Acid; MLN 8054 O-β-D-Glucuronide

Database IDs

• CAS Number: 1203589-02-9
• PubChem SID: 164230341
• PubChem CID: 44514023

CALCULATED PROPERTIES

• Acid pKa: 3.27479
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 2.0652266
• LogD (pH = 7.4): 0.9845151
• Log P: 3.962978
• Molar Refractivity: 156.795 cm^3
• Polarizability: 60.874535 Å^3
• Polar Surface Area: 183.69 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M425130

A metabolite of MLN 8054 (M425125).

REFERENCES

• Aliagas-Martin, I., et al.: J. Med. Chem., 52, 3300 (2009)
• Kaestner, P., et al.: Mol. Cancer Ther., 8, 2046 (2009)
• Scutt, P., et al.: J. Biol. Chem., 284, 15880 (2009)