2-{[(2S)-2-butyl-6,7-dichloro-2-cyclopentyl-1-oxo-2,3-dihydro-1H-inden-5-yl]oxy}acetic acid

• ChemBase ID: 155523
• Molecular Formular: C20H24Cl2O4
• Molecular Mass: 399.30816
• Monoisotopic Mass: 398.10516461
• SMILES: CCCC[C@]1(Cc2cc(c(c(c2C1=O)Cl)Cl)OCC(=O)O)C1CCCC1
• Canonical SMILES: CCCC[C@]1(Cc2c(C1=O)c(Cl)c(c(c2)OCC(=O)O)Cl)C1CCCC1
• InChI: InChI=1S/C20H24Cl2O4/c1-2-3-8-20(13-6-4-5-7-13)10-12-9-14(26-11-15(23)24)17(21)18(22)16(12)19(20)25/h9,13H,2-8,10-11H2,1H3,(H,23,24)/t20-/m0/s1
• InChIKey: YAWWQIFONIPBKT-FQEVSTJZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(2S)-2-butyl-6,7-dichloro-2-cyclopentyl-1-oxo-2,3-dihydro-1H-inden-5-yl]oxy}acetic acid
• IUPAC Traditional name: {[(2S)-2-butyl-6,7-dichloro-2-cyclopentyl-1-oxo-3H-inden-5-yl]oxy}acetic acid
• Synonyms: R(+)-Butylindazone; R-(+)-[(2-n-Butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-oxo-1H-inden-5-yl)oxy]acetic acid; R-(+)-DIOA

Database IDs

• CAS Number: 81166-47-4
• MDL Number: MFCD00069261
• PubChem SID: 24277830; 162249661
• PubChem CID: 10386195

CALCULATED PROPERTIES

• Acid pKa: 3.0295932
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.5191321
• LogD (pH = 7.4): 2.483691
• Log P: 5.9546633
• Molar Refractivity: 101.311 cm^3
• Polarizability: 39.763493 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: insoluble; 0.1 M NaOH: soluble; DMSO: >20 mg/mL; ethanol: soluble; H2O: insoluble <0.11 mg/mL
• Apperance: white solid
• Optical Rotation: [α]27/D +18.1°, c = 0.7 in methanol(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H24Cl2O4

DETAILS

Sigma Aldrich - D129

Biochem/physiol Actions
Potent [K+,Cl-]-cotransport inhibitor that shows no side effects on the bumetanimide-sensitive [Na+,K+,Cl-]-cotransport system.