N-(5-bromo-2-methoxybenzenesulfonyl)-3-[2-(naphthalen-2-ylmethyl)phenyl]prop-2-enamide

• ChemBase ID: 154664
• Molecular Formular: C27H22BrNO4S
• Molecular Mass: 536.43688
• Monoisotopic Mass: 535.04529119
• SMILES: COc1ccc(cc1S(=O)(=O)NC(=O)/C=C\c1ccccc1Cc1ccc2ccccc2c1)Br
• Canonical SMILES: COc1ccc(cc1S(=O)(=O)NC(=O)/C=C\c1ccccc1Cc1ccc2c(c1)cccc2)Br
• InChI: InChI=1S/C27H22BrNO4S/c1-33-25-14-13-24(28)18-26(25)34(31,32)29-27(30)15-12-21-7-3-5-9-23(21)17-19-10-11-20-6-2-4-8-22(20)16-19/h2-16,18H,17H2,1H3,(H,29,30)
• InChIKey: ODTKFNUPVBULRJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(5-bromo-2-methoxybenzenesulfonyl)-3-[2-(naphthalen-2-ylmethyl)phenyl]prop-2-enamide
• IUPAC Traditional name: N-(5-bromo-2-methoxybenzenesulfonyl)-3-[2-(naphthalen-2-ylmethyl)phenyl]prop-2-enamide
• Synonyms: (2E)-N-[(5-bromo-2-methoxyphenyl)sulfonyl]-3-[2-(2-naphthalenylmethyl)phenyl]-2-propenamide; L-798106

Database IDs

• CAS Number: 244101-02-8
• MDL Number: MFCD08272644
• PubChem SID: 162248802
• PubChem CID: 71311930

CALCULATED PROPERTIES

• Acid pKa: 4.296832
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 5.840463
• LogD (pH = 7.4): 5.6793747
• Log P: 6.619669
• Molar Refractivity: 138.4714 cm^3
• Polarizability: 54.657303 Å^3
• Polar Surface Area: 72.47 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

Safety Information

• German water hazard class: 3
• GHS Hazard statements: H413
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C27H22BrNO4S

DETAILS

Sigma Aldrich - L4545

Biochem/physiol Actions
L-798106 was among the first prostanoid receptor EP3-selective antagonists. It has been used in multiple studies to tease out EP3 agonist activity, both in vitro and in vivo. It successfully blocks the actions of sulprostone, an EP3-selective agonist, and it helped show that the vascular contraction effect of PGE2 is due to its prostanoid EP3 agonist activity.1