2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol

• ChemBase ID: 164948
• Molecular Formular: C18H20O5
• Molecular Mass: 316.3484
• Monoisotopic Mass: 316.13107374
• SMILES: c1c(c(c(cc1/C=C\c1ccc(c(c1)O)OC)OC)OC)OC
• Canonical SMILES: COc1cc(/C=C\c2ccc(c(c2)O)OC)cc(c1OC)OC
• InChI: InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5-
• InChIKey: HVXBOLULGPECHP-WAYWQWQTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
• IUPAC Traditional name: combretastatin A-4
• Synonyms: (Z)-2-Methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenol, 3,4,5-Trimethoxy-3’-hydroxy-4’-methoxy-(Z)-stilbene; CS-A4; Combretastatin A4

Database IDs

• CAS Number: 117048-59-6
• PubChem SID: 162259082
• PubChem CID: 5351344

CALCULATED PROPERTIES

• Acid pKa: 9.8428755
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.3788168
• LogD (pH = 7.4): 3.3772833
• Log P: 3.3788364
• Molar Refractivity: 89.3465 cm^3
• Polarizability: 34.18741 Å^3
• Polar Surface Area: 57.15 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Hexane
• Apperance: Off-White Solid
• Melting Point: 114-116°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C643000

Combretastatin is 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 and Poly(ADP-

REFERENCES

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