diethyl ({4-[(4-bromo-2-cyanophenyl)carbamoyl]phenyl}methyl)phosphonate

• ChemBase ID: 127779
• Molecular Formular: C19H20BrN2O4P
• Molecular Mass: 451.250861
• Monoisotopic Mass: 450.03440576
• SMILES: Brc1cc(C#N)c(NC(=O)c2ccc(cc2)CP(=O)(OCC)OCC)cc1
• Canonical SMILES: CCOP(=O)(Cc1ccc(cc1)C(=O)Nc1ccc(cc1C#N)Br)OCC
• InChI: InChI=1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23)
• InChIKey: KPRTURMJVWXURQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl ({4-[(4-bromo-2-cyanophenyl)carbamoyl]phenyl}methyl)phosphonate
• IUPAC Traditional name: ibrolipim
• Synonyms: Diethyl 4-[(4-bromo-2-cyanophenyl)carbamoyl]benzylphosphonate; Ibrolipim; OPF 009; NO-1886; Ibrolipim

Database IDs

• CAS Number: 133208-93-2
• MDL Number: MFCD00897807
• PubChem SID: 162222097
• PubChem CID: 131601
• Chemspider ID: 116297
• KEGG ID: D03747
• Wikipedia Title: Ibrolipim

CALCULATED PROPERTIES

• Acid pKa: 9.7559805
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.0247707
• LogD (pH = 7.4): 4.022951
• Log P: 4.0247936
• Molar Refractivity: 109.2541 cm^3
• Polarizability: 41.48232 Å^3
• Polar Surface Area: 88.42 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: off-white to pale yellow powder

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H20BrN2O4P

DETAILS

Sigma Aldrich - N1540

Biochem/physiol Actions
Lipoprotein lipase activator. Overexpression of lipoprotein lipase in transgenic rabbits leads to increased small dense LDL in plasma and promotes atherosclerosis. Long-term administration of NO-1886 protects against the development of experimental atherosclerosis in animals.
Packaging
Packaged under nitrogen