3-[(3-hydroxy-4-methoxyphenyl)methylidene]-6-methyl-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 154143
• Molecular Formular: C18H16O4
• Molecular Mass: 296.31724
• Monoisotopic Mass: 296.10485899
• SMILES: Cc1ccc2c(c1)C(=O)/C(=C/c1ccc(c(c1)O)OC)/CO2
• Canonical SMILES: COc1ccc(cc1O)/C=C/1\COc2c(C1=O)cc(cc2)C
• InChI: InChI=1S/C18H16O4/c1-11-3-5-16-14(7-11)18(20)13(10-22-16)8-12-4-6-17(21-2)15(19)9-12/h3-9,19H,10H2,1-2H3
• InChIKey: BZCADTHMZLYKAR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(3-hydroxy-4-methoxyphenyl)methylidene]-6-methyl-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: 3-[(3-hydroxy-4-methoxyphenyl)methylidene]-6-methyl-2H-1-benzopyran-4-one
• Synonyms: 3-[1-(3-Hydroxy-4-methoxyphenyl)-meth-(E)-ylidene]-6-methyl-chroman-4-one; IMS2186

Database IDs

• CAS Number: 1031206-36-6
• MDL Number: MFCD12912419
• PubChem SID: 162248282
• PubChem CID: 24987039

CALCULATED PROPERTIES

• Acid pKa: 9.815247
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.4181743
• LogD (pH = 7.4): 3.4165404
• Log P: 3.4181952
• Molar Refractivity: 84.696 cm^3
• Polarizability: 32.003765 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white to off-white solid

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H16O4

DETAILS

Sigma Aldrich - I7160

Biochem/physiol Actions
IMS2186 is an anti-proliferative and anti-angiogenic agent. Apparently IMS2186 blocks the cell cycle at G2 and inhibits the production of PGE2/TNF-α. IMS2186 inhibits cell growth in vitro in tumor cells, non-transformed fibroblasts, and retinal pigment epithelial cells. IMS2186 inhibits angiogenesis (IC50 = 0.1 μM) and cell migration. Intraocular injection of IMS2186 could be a long-lasting effective treatment for CNV (choroidal neovascularization) in AMD (age-related macular degeneration) with a reduction in scarring and related visual loss.