N-{4-chloro-2-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]phenyl}-2-hydroxybenzamide

• ChemBase ID: 154542
• Molecular Formular: C22H15ClN2O4
• Molecular Mass: 406.8185
• Monoisotopic Mass: 406.07203465
• SMILES: c1ccc2c(c1)C(=O)N(C2=O)Cc1cc(ccc1NC(=O)c1ccccc1O)Cl
• Canonical SMILES: Clc1ccc(c(c1)CN1C(=O)c2c(C1=O)cccc2)NC(=O)c1ccccc1O
• InChI: InChI=1S/C22H15ClN2O4/c23-14-9-10-18(24-20(27)17-7-3-4-8-19(17)26)13(11-14)12-25-21(28)15-5-1-2-6-16(15)22(25)29/h1-11,26H,12H2,(H,24,27)
• InChIKey: UFOUABRZSDGGAZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{4-chloro-2-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]phenyl}-2-hydroxybenzamide
• IUPAC Traditional name: N-{4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl}-2-hydroxybenzamide
• Synonyms: N-[4-Chloro-2-(phthalimidomethyl)phenyl]salicylamide; N-[4-Chloro-2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}-2-hydroxybenzamide; CPPHA

Database IDs

• CAS Number: 693288-97-0
• MDL Number: MFCD12912405
• PubChem SID: 162248681
• PubChem CID: 9931205

CALCULATED PROPERTIES

• Acid pKa: 7.929238
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.0323353
• LogD (pH = 7.4): 3.9224107
• Log P: 4.0339365
• Molar Refractivity: 111.1433 cm^3
• Polarizability: 40.674038 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: solid

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H410
• GHS Precautionary statements: P273-P501
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H15ClN2O4

DETAILS

Sigma Aldrich - C2247

Biochem/physiol Actions
CPPHA is a selective positive allosteric modulator of mGluR5 receptor. It has no agonist activity alone, but reduces threshold response and shifts dose-response curves to glutamate, quisqualate, and DHPG by 4- to 7-fold to the left in recombinant CHO cells expressing human or rat mGluR5.