methyl (2S)-2-(naphthalen-1-ylformamido)-3-(4-nitrophenyl)propanoate

• ChemBase ID: 153268
• Molecular Formular: C21H18N2O5
• Molecular Mass: 378.37802
• Monoisotopic Mass: 378.12157169
• SMILES: COC(=O)[C@H](Cc1ccc(cc1)[N+](=O)[O-])NC(=O)c1cccc2c1cccc2
• Canonical SMILES: COC(=O)[C@@H](NC(=O)c1cccc2c1cccc2)Cc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C21H18N2O5/c1-28-21(25)19(13-14-9-11-16(12-10-14)23(26)27)22-20(24)18-8-4-6-15-5-2-3-7-17(15)18/h2-12,19H,13H2,1H3,(H,22,24)/t19-/m0/s1
• InChIKey: VMFGCGRAIBLAFY-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-(naphthalen-1-ylformamido)-3-(4-nitrophenyl)propanoate
• IUPAC Traditional name: methyl (2S)-2-(naphthalen-1-ylformamido)-3-(4-nitrophenyl)propanoate
• Synonyms: L-Phenylalanine, N-(1-naphthalenylcarbonyl)-4-nitro-, methyl ester; SB 328437

Database IDs

• CAS Number: 247580-43-4
• MDL Number: MFCD16618397
• PubChem SID: 162247407
• PubChem CID: 10474776

CALCULATED PROPERTIES

• Acid pKa: 15.415244
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.825991
• LogD (pH = 7.4): 3.8259912
• Log P: 3.8259912
• Molar Refractivity: 103.7746 cm^3
• Polarizability: 40.244514 Å^3
• Polar Surface Area: 101.22 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H18N2O5

DETAILS

Sigma Aldrich - SML0207

Biochem/physiol Actions
SB-328437 is a potent, selective CCR-3 antagonist (IC50 = 1.6 nM). The compound blockes CCR3 agonist-induced calcium mobilization in CCR3 expressing cells with the following IC50 values: eotaxin, 38 nM; eotaxin-2, 35 nM and MCP4, 20 nM.