3-phenylprop-2-en-1-yl 2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enoate

• ChemBase ID: 153291
• Molecular Formular: C19H15NO4
• Molecular Mass: 321.3267
• Monoisotopic Mass: 321.10010797
• SMILES: c1ccc(cc1)/C=C/COC(=O)/C(=C\c1ccc(c(c1)O)O)/C#N
• Canonical SMILES: N#C/C(=C/c1ccc(c(c1)O)O)/C(=O)OC/C=C/c1ccccc1
• InChI: InChI=1S/C19H15NO4/c20-13-16(11-15-8-9-17(21)18(22)12-15)19(23)24-10-4-7-14-5-2-1-3-6-14/h1-9,11-12,21-22H,10H2
• InChIKey: XGHYFEJMJXGPGN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-phenylprop-2-en-1-yl 2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enoate
• IUPAC Traditional name: 3-phenylprop-2-en-1-yl 2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enoate
• Synonyms: CDC; Cinnamyl-3,4-dihydroxy-α-cyanocinnamate

Database IDs

• CAS Number: 132465-11-3
• MDL Number: MFCD00210839
• PubChem SID: 162247430
• PubChem CID: 9905190

CALCULATED PROPERTIES

• Acid pKa: 8.4131975
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.053904
• LogD (pH = 7.4): 4.014503
• Log P: 4.0544305
• Molar Refractivity: 91.7756 cm^3
• Polarizability: 34.28951 Å^3
• Polar Surface Area: 90.55 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥15 mg/mL
• Apperance: light yellow to yellow powder

Safety Information

• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H15NO4

DETAILS

Sigma Aldrich - SML0105

Biochem/physiol Actions
Cinnamyl-3,4-dihydroxy-α-cyanocinnamate (CDC) is a potent and direct inhibitor of 5-LO (5-Lipoxygenase) that reduces 5-LO activity in cell-free assays. CDC also inhibits 12-LO and 15-LO