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

• ChemBase ID: 154962
• Molecular Formular: C18H12N2O2
• Molecular Mass: 288.30008
• Monoisotopic Mass: 288.08987763
• SMILES: c1ccc(cc1)n1cc(c2c1cccc2)/C=C(/C#N)\C(=O)O
• 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)
• InChIKey: BIZNHCWFGNKBBZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-cyano-3-(1-phenyl-1H-indol-3-yl)prop-2-enoic acid
• IUPAC Traditional name: 2-cyano-3-(1-phenylindol-3-yl)prop-2-enoic acid
• Synonyms: 2-Cyano-3-(1-phenyl-1H-indol-3-yl)-2-propenoic acid; PF-1005023; UK-5099

Database IDs

• CAS Number: 56396-35-1
• MDL Number: MFCD19443867
• PubChem SID: 162249100
• PubChem CID: 20839118

CALCULATED PROPERTIES

• Acid pKa: 3.2414708
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.6125976
• LogD (pH = 7.4): 0.30120504
• 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: >20 mg/mL
• Apperance: yellow to tan 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): C18H12N2O2

DETAILS

Sigma Aldrich - PZ0160

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
UK-5099 is a potent inhibitor of the mitochondrial pyruvate transporter. n rat heart mitochondria, UK-5099 inhibits pyruvate-dependent O2 consumption with an IC50 of 50 nM.