3-(cyclohexylamino)-2-(phenylmethylidene)-2,3-dihydro-1H-inden-1-one hydrochloride

• ChemBase ID: 154743
• Molecular Formular: C22H24ClNO
• Molecular Mass: 353.88506
• Monoisotopic Mass: 353.15464207
• SMILES: c1ccc(cc1)/C=C\1/C(c2ccccc2C1=O)NC1CCCCC1.Cl
• Canonical SMILES: O=C1c2ccccc2C(/C/1=C/c1ccccc1)NC1CCCCC1.Cl
• InChI: InChI=1S/C22H23NO.ClH/c24-22-19-14-8-7-13-18(19)21(23-17-11-5-2-6-12-17)20(22)15-16-9-3-1-4-10-16;/h1,3-4,7-10,13-15,17,21,23H,2,5-6,11-12H2;1H
• InChIKey: JPATUDRDKCLPTI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(cyclohexylamino)-2-(phenylmethylidene)-2,3-dihydro-1H-inden-1-one hydrochloride
• IUPAC Traditional name: 3-(cyclohexylamino)-2-(phenylmethylidene)-3H-inden-1-one hydrochloride
• Synonyms: (E)-2-benzylidene-3-(cyclohexylamino)-2,3-dihydro-1H-inden-1-one; 3-(cyclohexylamino)-2,3-dihydro-2-(phenylmethylene)-1Hinden-1-one; 2-benzylidene-3-(cyclohexylamino)-1-Indanone hydrochloride; NSC 150117 hydrochloride; (E/Z)-BCI hydrochloride

Database IDs

• CAS Number: 95130-23-7
• MDL Number: MFCD16875416
• PubChem SID: 162248881
• PubChem CID: 20831631

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.0806491
• LogD (pH = 7.4): 3.7250214
• Log P: 4.941068
• Molar Refractivity: 98.6799 cm^3
• Polarizability: 38.35296 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: yellow powder

Safety Information

• Storage Condition: desiccated
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H23NO · HCl

DETAILS

Sigma Aldrich - B4313

Biochem/physiol Actions
BCI is an allosteric inhibitor of Dusp6 that acts within the phosphatase domain to prevent the catalytic stimulation of phosphatase activity induced by ERK2 substrate binding. BCI also hyperactivates FGF signaling, since Dusp6 functions as a feedback regulator of FGF signaling.