(2E)-N-{4-[(3-methoxypyrazin-2-yl)sulfamoyl]phenyl}-3-(5-nitrothiophen-2-yl)prop-2-enamide

• ChemBase ID: 175051
• Molecular Formular: C18H15N5O6S2
• Molecular Mass: 461.4716
• Monoisotopic Mass: 461.04637523
• SMILES: c1(nccnc1OC)NS(=O)(=O)c1ccc(cc1)NC(=O)/C=C/c1ccc(s1)[N+](=O)[O-]
• Canonical SMILES: COc1nccnc1NS(=O)(=O)c1ccc(cc1)NC(=O)/C=C/c1ccc(s1)[N+](=O)[O-]
• InChI: InChI=1S/C18H15N5O6S2/c1-29-18-17(19-10-11-20-18)22-31(27,28)14-6-2-12(3-7-14)21-15(24)8-4-13-5-9-16(30-13)23(25)26/h2-11H,1H3,(H,19,22)(H,21,24)/b8-4+
• InChIKey: FNPPHVLYVGMZMZ-XBXARRHUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-N-{4-[(3-methoxypyrazin-2-yl)sulfamoyl]phenyl}-3-(5-nitrothiophen-2-yl)prop-2-enamide
• IUPAC Traditional name: necrosulfonamide
• Synonyms: N-[4-[[(3-Methoxypyrazinyl)amino]sulfonyl]phenyl]-3-(5-nitro-2-thienyl)-2-propenamide; (E)-N-[4-[N-(3-methoxypyrazin-2-yl)sulfamoyl]phenyl]-3-(5-nitrothiophene-2-yl)acrylamide; Necrosulfonamide

Database IDs

• CAS Number: 432531-71-0
• PubChem SID: 164230961
• PubChem CID: 1566236

CALCULATED PROPERTIES

• Acid pKa: 5.704596
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 2.4920127
• LogD (pH = 7.4): 1.7919104
• Log P: 2.672814
• Molar Refractivity: 114.3203 cm^3
• Polarizability: 42.831818 Å^3
• Polar Surface Area: 156.1 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 200-204°C(dec.)

Safety Information

• Storage Condition: Amber Vial, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - N388600

Necrosulfonamide specifically blocks necrosis downstream of receptor-interacting serine-threonine kinase 3 (RIP3) activation. RIP3 is a key signalling molecule in the programmed necrosis (necroptosis) pathway.

REFERENCES

• Sun, L. et al.: Cell, 148, 213 (2012)