3-{1-[(4-chlorophenyl)methyl]-5-fluoro-3-methyl-1H-indol-2-yl}-2,2-dimethylpropanoic acid

• ChemBase ID: 153127
• Molecular Formular: C21H21ClFNO2
• Molecular Mass: 373.8483432
• Monoisotopic Mass: 373.12448482
• SMILES: Cc1c2cc(ccc2n(c1CC(C)(C)C(=O)O)Cc1ccc(cc1)Cl)F
• Canonical SMILES: Clc1ccc(cc1)Cn1c(CC(C(=O)O)(C)C)c(c2c1ccc(c2)F)C
• InChI: InChI=1S/C21H21ClFNO2/c1-13-17-10-16(23)8-9-18(17)24(12-14-4-6-15(22)7-5-14)19(13)11-21(2,3)20(25)26/h4-10H,11-12H2,1-3H3,(H,25,26)
• InChIKey: JLPYLHLUHJOPNL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{1-[(4-chlorophenyl)methyl]-5-fluoro-3-methyl-1H-indol-2-yl}-2,2-dimethylpropanoic acid
• IUPAC Traditional name: 3-{1-[(4-chlorophenyl)methyl]-5-fluoro-3-methylindol-2-yl}-2,2-dimethylpropanoic acid
• Synonyms: 3-[1-(4-Chlorobenzyl)-5-fluoro-3-methyl-indol-2-yl]-2,2-dimethyl propanoic acid; L-655,240

Database IDs

• CAS Number: 103253-15-2
• MDL Number: MFCD04040005
• PubChem SID: 24278524; 162247267
• PubChem CID: 122070

CALCULATED PROPERTIES

• Acid pKa: 4.5174656
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.2014227
• LogD (pH = 7.4): 3.4309313
• Log P: 6.225736
• Molar Refractivity: 101.7318 cm^3
• Polarizability: 39.873837 Å^3
• Polar Surface Area: 42.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble30 mg/mL; H2O: insoluble
• Apperance: off-white solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 36/37/39
• 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 ... TBXA2R(6915)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H21O2NClF

DETAILS

Sigma Aldrich - L9539

Biochem/physiol Actions
Thromboxane A2 receptor antagonist, induces platelet aggregation and contraction of vascular and smooth muscle. Increases PI turnover with elevation of intracellular free Ca2+.