2-{1-[(4-fluorophenyl)methyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid

• ChemBase ID: 155759
• Molecular Formular: C19H18FNO3
• Molecular Mass: 327.3495232
• Monoisotopic Mass: 327.12707166
• SMILES: Cc1c(c2cc(ccc2n1Cc1ccc(cc1)F)OC)CC(=O)O
• Canonical SMILES: COc1ccc2c(c1)c(CC(=O)O)c(n2Cc1ccc(cc1)F)C
• InChI: InChI=1S/C19H18FNO3/c1-12-16(10-19(22)23)17-9-15(24-2)7-8-18(17)21(12)11-13-3-5-14(20)6-4-13/h3-9H,10-11H2,1-2H3,(H,22,23)
• InChIKey: DIGWWZCEDODOMZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{1-[(4-fluorophenyl)methyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid
• IUPAC Traditional name: {1-[(4-fluorophenyl)methyl]-5-methoxy-2-methylindol-3-yl}acetic acid
• Synonyms: 1-(4-Fluorobenzyl)-5-methoxy-2-methylindole-3-acetic acid

Database IDs

• MDL Number: MFCD03452919
• PubChem SID: 24278434; 162249897
• PubChem CID: 3448892

CALCULATED PROPERTIES

• Acid pKa: 4.2090516
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.5323746
• LogD (pH = 7.4): 0.8152201
• Log P: 3.8424973
• Molar Refractivity: 89.7907 cm^3
• Polarizability: 35.002132 Å^3
• Polar Surface Area: 51.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥18 mg/mL
• Apperance: off-white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ABCC1(4363)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H18NFO3

DETAILS

Sigma Aldrich - F2927

Biochem/physiol Actions
Putative inhibitor of multidrug resistance-associated protein 1 (MRP1).
Other Notes
N-benzoyl analog of indomethacin