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

• ChemBase ID: 156051
• Molecular Formular: C19H18ClNO3
• Molecular Mass: 343.80412
• Monoisotopic Mass: 343.09752112
• SMILES: Cc1c(c2cc(ccc2n1Cc1ccc(cc1)Cl)OC)CC(=O)O
• Canonical SMILES: COc1ccc2c(c1)c(CC(=O)O)c(n2Cc1ccc(cc1)Cl)C
• InChI: InChI=1S/C19H18ClNO3/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: ZCEPWIDYPWMCOY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• MDL Number: MFCD03453282
• PubChem SID: 162250189; 24278299
• PubChem CID: 4059895

CALCULATED PROPERTIES

• Acid pKa: 4.293851
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.0735393
• LogD (pH = 7.4): 1.3363781
• Log P: 4.30384
• Molar Refractivity: 94.3791 cm^3
• Polarizability: 37.210136 Å^3
• Polar Surface Area: 51.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble10 mg/mL; H2O: insoluble

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

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

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C19H18NO3Cl

DETAILS

Sigma Aldrich - C1610

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