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

• ChemBase ID: 167798
• Molecular Formular: C18H17NO7
• Molecular Mass: 359.33008
• Monoisotopic Mass: 359.10050189
• SMILES: c1(c(ccc(c1)/C=C/C(=O)N[C@@H](Cc1ccc(c(c1)O)O)C(=O)O)O)O
• Canonical SMILES: O=C(N[C@H](C(=O)O)Cc1ccc(c(c1)O)O)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/b6-3+/t12-/m0/s1
• InChIKey: GPZFXSWMDFBRGS-UXONFWTHSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 53755-02-5
• PubChem SID: 162261931
• PubChem CID: 6506968

CALCULATED PROPERTIES

• Acid pKa: 3.2233875
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -0.21545269
• LogD (pH = 7.4): -1.4119526
• Log P: 2.0416324
• Molar Refractivity: 92.8999 cm^3
• Polarizability: 35.035614 Å^3
• Polar Surface Area: 147.32 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 108-112°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D452500

It was identified in the antioxidant polyphenolic fraction of cocoa (Theobroma cacao L.). As a naturally occurring caffeoyl conjugate, Clovamide 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)