(3-{[1-benzyl-3-(carbamoylmethyl)-2-ethyl-1H-indol-5-yl]oxy}propyl)phosphonic acid

• ChemBase ID: 154952
• Molecular Formular: C22H27N2O5P
• Molecular Mass: 430.433941
• Monoisotopic Mass: 430.1657586
• SMILES: CCc1c(c2cc(ccc2n1Cc1ccccc1)OCCCP(=O)(O)O)CC(=O)N
• Canonical SMILES: CCc1c(CC(=O)N)c2c(n1Cc1ccccc1)ccc(c2)OCCCP(=O)(O)O
• InChI: InChI=1S/C22H27N2O5P/c1-2-20-19(14-22(23)25)18-13-17(29-11-6-12-30(26,27)28)9-10-21(18)24(20)15-16-7-4-3-5-8-16/h3-5,7-10,13H,2,6,11-12,14-15H2,1H3,(H2,23,25)(H2,26,27,28)
• InChIKey: OPWQYOUZRHDKBR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-{[1-benzyl-3-(carbamoylmethyl)-2-ethyl-1H-indol-5-yl]oxy}propyl)phosphonic acid
• IUPAC Traditional name: 3-{[1-benzyl-3-(carbamoylmethyl)-2-ethylindol-5-yl]oxy}propylphosphonic acid
• Synonyms: LY311727

Database IDs

• CAS Number: 164083-84-5
• MDL Number: MFCD00943218
• PubChem SID: 162249090
• PubChem CID: 155922

CALCULATED PROPERTIES

• Acid pKa: 1.8091886
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.21356747
• LogD (pH = 7.4): -0.2822874
• Log P: 2.075504
• Molar Refractivity: 116.1187 cm^3
• Polarizability: 45.737404 Å^3
• Polar Surface Area: 114.78 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥15 mg/mL
• Apperance: white to tan powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H27N2O5P

DETAILS

Sigma Aldrich - L6795

Biochem/physiol Actions
LY311727 is an orally active; potent secretory Phospholipase A2 (sPLA2; Group IIa) inhibitor.