2-(1-cyclohexanecarbonyl-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid

• ChemBase ID: 155761
• Molecular Formular: C19H23NO4
• Molecular Mass: 329.39022
• Monoisotopic Mass: 329.16270822
• SMILES: Cc1c(c2cc(ccc2n1C(=O)C1CCCCC1)OC)CC(=O)O
• Canonical SMILES: COc1ccc2c(c1)c(CC(=O)O)c(n2C(=O)C1CCCCC1)C
• InChI: InChI=1S/C19H23NO4/c1-12-15(11-18(21)22)16-10-14(24-2)8-9-17(16)20(12)19(23)13-6-4-3-5-7-13/h8-10,13H,3-7,11H2,1-2H3,(H,21,22)
• InChIKey: AWPBTRHQEYHZJD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1-cyclohexanecarbonyl-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid
• IUPAC Traditional name: (1-cyclohexanecarbonyl-5-methoxy-2-methylindol-3-yl)acetic acid
• Synonyms: 1-Benzoyl-5-methoxy-2-methylindole-3-acetic acid

Database IDs

• MDL Number: MFCD03452837
• PubChem SID: 24278255; 162249899
• PubChem CID: 11695602

CALCULATED PROPERTIES

• Acid pKa: 4.2099047
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.8756409
• LogD (pH = 7.4): 0.15826437
• Log P: 3.1849575
• Molar Refractivity: 90.5375 cm^3
• Polarizability: 36.215645 Å^3
• Polar Surface Area: 68.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble38 mg/mL; H2O: slightly soluble <0.17 mg/mL
• Apperance: 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: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C19H17NO4

DETAILS

Sigma Aldrich - B1183

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