(2E)-2-cyano-3-(1-phenyl-1H-indol-3-yl)prop-2-enoic acid

• ChemBase ID: 179379
• Molecular Formular: C18H12N2O2
• Molecular Mass: 288.30008
• Monoisotopic Mass: 288.08987763
• SMILES: c1cccc(c1)n1c2c(c(c1)/C=C(/C(=O)O)\C#N)cccc2
• Canonical SMILES: N#C/C(=C\c1cn(c2c1cccc2)c1ccccc1)/C(=O)O
• InChI: InChI=1S/C18H12N2O2/c19-11-13(18(21)22)10-14-12-20(15-6-2-1-3-7-15)17-9-5-4-8-16(14)17/h1-10,12H,(H,21,22)/b13-10+
• InChIKey: BIZNHCWFGNKBBZ-JLHYYAGUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-2-cyano-3-(1-phenyl-1H-indol-3-yl)prop-2-enoic acid
• IUPAC Traditional name: (2E)-2-cyano-3-(1-phenylindol-3-yl)prop-2-enoic acid
• Synonyms: 2-Cyano-3-(1-phenyl-1H-indol-3-yl)-2-propenoic Acid; UK 5099; PF-06340678; UK-5099

Database IDs

• CAS Number: 56396-35-1
• PubChem SID: 164235289
• PubChem CID: 6438504

CALCULATED PROPERTIES

• Acid pKa: 3.0414708
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.422633
• LogD (pH = 7.4): 0.25920823
• Log P: 3.8574
• Molar Refractivity: 94.1936 cm^3
• Polarizability: 33.39272 Å^3
• Polar Surface Area: 66.02 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: 235-238°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - U700550

Inhibitor of plasma membrane monocarboxylate transporters (MCTs) and the mitochondrial pyruvate carrier (MPC).

REFERENCES

• Wiemer, E.A. et al.: Biochem. J., 312, 479 (1995)
• Hildyard, J.C. et al.: Biochem. J., 374, 607 (1995)
• Hinoi, E. et al.: Mol. Pharmacol., 70, 925 (1995)