4-(3-{[(2-cyclopentyl-6,7-dimethyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy]methyl}phenyl)benzoic acid

• ChemBase ID: 154915
• Molecular Formular: C30H30O4
• Molecular Mass: 454.5568
• Monoisotopic Mass: 454.21440944
• SMILES: Cc1c(c2c(cc1OCc1cccc(c1)c1ccc(cc1)C(=O)O)CC(C2=O)C1CCCC1)C
• Canonical SMILES: Cc1c(OCc2cccc(c2)c2ccc(cc2)C(=O)O)cc2c(c1C)C(=O)C(C2)C1CCCC1
• InChI: InChI=1S/C30H30O4/c1-18-19(2)28-25(15-26(29(28)31)22-7-3-4-8-22)16-27(18)34-17-20-6-5-9-24(14-20)21-10-12-23(13-11-21)30(32)33/h5-6,9-14,16,22,26H,3-4,7-8,15,17H2,1-2H3,(H,32,33)
• InChIKey: KMKBEESNZAPKMP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(3-{[(2-cyclopentyl-6,7-dimethyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy]methyl}phenyl)benzoic acid
• IUPAC Traditional name: biphenylindanone A
• Synonyms: 3′-[[(2-cyclopentyl-6,7-dimethyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy]methyl]biphenyl-4-carboxylic acid; BINA; Biphenylindanone A; Biphenyl-indanone A

Database IDs

• CAS Number: 866823-73-6
• MDL Number: MFCD19440914
• PubChem SID: 162249053
• PubChem CID: 9868580

CALCULATED PROPERTIES

• Acid pKa: 4.0701714
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 5.9927554
• LogD (pH = 7.4): 4.317545
• Log P: 7.434994
• Molar Refractivity: 134.4002 cm^3
• Polarizability: 52.58587 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥18 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C30H30O4

DETAILS

Sigma Aldrich - B8688

Biochem/physiol Actions
Biphenyl-indanone A (BINA) is a potent selective positive allosteric modulator for the group II metabotropic glutamate receptor subtype mGluR2. In animal studies BINA showed anxiolytic and antipsychotic effects, and blocked the effects produced by the hallucinogenic drug DOB. It decreased cocaine self-administration in rats, with no effect on food self-administration. In recombinant systems, BINA selectively potentiated the response of mGluR2 to glutamate with no effect on the glutamate response of other mGluR receptor subtypes tested.