(2S)-2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]pentanedioic acid

• ChemBase ID: 167797
• Molecular Formular: C14H15NO7
• Molecular Mass: 309.2714
• Monoisotopic Mass: 309.08485183
• SMILES: c1(c(ccc(c1)/C=C/C(=O)N[C@@H](CCC(=O)O)C(=O)O)O)O
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C14H15NO7/c16-10-4-1-8(7-11(10)17)2-5-12(18)15-9(14(21)22)3-6-13(19)20/h1-2,4-5,7,9,16-17H,3,6H2,(H,15,18)(H,19,20)(H,21,22)/b5-2+/t9-/m0/s1
• InChIKey: PRCRWIWEDONYKC-MAHOQKISSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]pentanedioic acid
• IUPAC Traditional name: (2S)-2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]pentanedioic acid
• Synonyms: N-[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]-L-glutamic Acid; N-[3',4'-Dihydroxy-(E)-cinnamoyl]-L-glutamic Acid

Database IDs

• CAS Number: 860295-23-4
• PubChem SID: 162261930
• PubChem CID: 26496524

CALCULATED PROPERTIES

• Acid pKa: 3.1962912
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -3.0615435
• LogD (pH = 7.4): -5.943246
• Log P: 0.6392859
• Molar Refractivity: 75.1095 cm^3
• Polarizability: 28.52582 Å^3
• Polar Surface Area: 144.16 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D452480

It was identified in the antioxidant polyphenolic fraction of cocoa (Theobroma cacao L.). As a naturally occurring caffeoyl conjugate, it represents an interesting antiradical/antioxidant compound.

REFERENCES

• Azizah, A., et al.: Food Chem., 64, 199 (1999)
• Mao, T., et al.: J. Med. Food, 5, 17 (1999)
• Park, J., et al.: J. Agric. Food Chem., 53, 8135 (1999)
• Zhu, Q., et al.: Clin. Develop. Immunol., 12, 27 (1999)