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

• ChemBase ID: 126674
• Molecular Formular: C18H20O5
• Molecular Mass: 316.3484
• Monoisotopic Mass: 316.13107374
• SMILES: COc1c(cc(cc1)/C=C/c1cc(c(c(c1)OC)OC)OC)O
• 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
• InChIKey: HVXBOLULGPECHP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
• IUPAC Traditional name: combretastatin A-4
• Synonyms: Combretastatin A4; CA-4; Combretastatin A-4; 1-(3,4,5-Trimethoxyphenyl)-2-(3′-hydroxy-4′-methoxyphenyl) ethane 3,4,5-trimethoxy-3′-hydroxy-4′-methoxystilbene; 2-Methoxy-5-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol; CA4; Combretastatin A4

Database IDs

• CAS Number: 117048-59-6
• MDL Number: MFCD03453309
• PubChem SID: 162221004
• PubChem CID: 5351344; 5386397
• CHEMBL: 67
• Chemspider ID: 4508364
• Wikipedia Title: Combretastatin_A-4

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: DMSO: >10 mg/mL
• Apperance: off-white powder
• Melting Point: 116 °C

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25-41
• Safety Statements: 26-36/37-39-45
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H318-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H20O5

DETAILS

Sigma Aldrich - C7744

Biochem/physiol Actions
Combretastatin A4 is a vascular disrupting agent (VDA) that targets tumor vasculature to inhibit angiogenesis. It inhibits tubulin polymerization at the colchicine-binding site of beta-tubulin. It has antitumor activity by inhibiting AKT function in human gastric cells. The inhibited AKT activation causes decreased cell proliferation, cell cycle arrest, and reduced in vitro migration/invasiveness and in vivo metastatic ability. Combretastatin A4 is a natural stilbenoid phenol.