N-[(3R)-1-[(4-chlorophenyl)methyl]pyrrolidin-3-yl]-2-{[3-(trifluoromethyl)phenyl]formamido}acetamide hydrochloride

• ChemBase ID: 154928
• Molecular Formular: C21H22Cl2F3N3O2
• Molecular Mass: 476.3194896
• Monoisotopic Mass: 475.10411698
• SMILES: c1cc(cc(c1)C(F)(F)F)C(=O)NCC(=O)N[C@@H]1CCN(C1)Cc1ccc(cc1)Cl.Cl
• Canonical SMILES: O=C(N[C@@H]1CCN(C1)Cc1ccc(cc1)Cl)CNC(=O)c1cccc(c1)C(F)(F)F.Cl
• InChI: InChI=1S/C21H21ClF3N3O2.ClH/c22-17-6-4-14(5-7-17)12-28-9-8-18(13-28)27-19(29)11-26-20(30)15-2-1-3-16(10-15)21(23,24)25;/h1-7,10,18H,8-9,11-13H2,(H,26,30)(H,27,29);1H/t18-;/m1./s1
• InChIKey: PGUQBBISBKGQDC-GMUIIQOCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R)-1-[(4-chlorophenyl)methyl]pyrrolidin-3-yl]-2-{[3-(trifluoromethyl)phenyl]formamido}acetamide hydrochloride
• IUPAC Traditional name: N-[(3R)-1-[(4-chlorophenyl)methyl]pyrrolidin-3-yl]-2-{[3-(trifluoromethyl)phenyl]formamido}acetamide hydrochloride
• Synonyms: N-[2-[[(3R)-1-[(4-chlorophenyl)methyl]-3-pyrrolidinyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide hydrochloride; Teijin compound 1 hydrochloride

Database IDs

• MDL Number: MFCD16618399
• PubChem SID: 162249066
• PubChem CID: 56972239

CALCULATED PROPERTIES

• Acid pKa: 13.139144
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.3407362
• LogD (pH = 7.4): 2.872214
• Log P: 3.1154916
• Molar Refractivity: 108.8134 cm^3
• Polarizability: 40.63059 Å^3
• Polar Surface Area: 61.44 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: white to tan powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H21ClF3N3O2·HCl

DETAILS

Sigma Aldrich - T7330

Biochem/physiol Actions
Teijin compound 1 is CCR2b receptor antagonist. Teijin compound 1 inhibits cell chemotaxis induced by MCP-1. The chemokine receptors CCR2 is G protein-coupled receptors (GPCR), and is mainly expressed in monocytes, immature dendritic cells, activated T-lymphocytes and basophils.