disodium 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl phosphate

• ChemBase ID: 164949
• Molecular Formular: C18H19Na2O8P
• Molecular Mass: 440.291961
• Monoisotopic Mass: 440.06129276
• SMILES: c1c(c(c(cc1/C=C\c1ccc(c(c1)OP(=O)([O-])[O-])OC)OC)OC)OC.[Na+].[Na+]
• Canonical SMILES: COc1cc(/C=C\c2ccc(c(c2)OP(=O)([O-])[O-])OC)cc(c1OC)OC.[Na+].[Na+]
• InChI: InChI=1S/C18H21O8P.2Na/c1-22-14-8-7-12(9-15(14)26-27(19,20)21)5-6-13-10-16(23-2)18(25-4)17(11-13)24-3;;/h5-11H,1-4H3,(H2,19,20,21);;/q;2*+1/p-2/b6-5-
• InChIKey: VXNQMUVMEIGUJW-XNOMRPDFSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl phosphate
• IUPAC Traditional name: disodium 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl phosphate
• Synonyms: 2-Methoxy-5-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol 1-(Dihydrogen phosphate) Sodium Salt; CA 4P; Combretastatin A4 Phosphate Disodium Salt; Fosbretabulin (Combretastatin A4 Phosphate,

Database IDs

• CAS Number: 168555-66-6
• PubChem SID: 162259083
• PubChem CID: 6918309

CALCULATED PROPERTIES

• Acid pKa: 1.6219862
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 0.3281389
• LogD (pH = 7.4): -0.51279986
• Log P: 2.7249713
• Molar Refractivity: 97.976 cm^3
• Polarizability: 38.30252 Å^3
• Polar Surface Area: 109.34 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 229-233°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Target: Microtubule Associated

Product Information

• Salt Data: Phosphate

DETAILS

Toronto Research Chemicals - C643025

Phosphorylated Combretastatin, a small organic molecule found in the bark of the African bush willow tree Combretum caffrum. Combretastatin-A4 Prodrug Induces Mitotic Catastrophe in Chronic Lymphocytic Leukemia Cell Line Independent of Caspase Activation

REFERENCES

• Hamel, E., et al.: Biochem. Pharmacol., 32, 3863 (1983)
• Chaplin, D.J., et al.: Br. J. Cancer, 74, S86, (1996)