(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)(1,2,3-13C3)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

• ChemBase ID: 164300
• Molecular Formular: C16H18O9
• Molecular Mass: 357.28668451
• Monoisotopic Mass: 357.10514667
• SMILES: C1[C@H]([C@H]([C@@H](C[C@]1(O)C(=O)O)O[13C](=O)/[13CH]=[13CH]/c1cc(c(cc1)O)O)O)O
• Canonical SMILES: O=[13C](O[C@@H]1C[C@@](O)(C[C@H]([C@H]1O)O)C(=O)O)/[13CH]=[13CH]/c1ccc(c(c1)O)O
• InChI: InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1/i2+1,4+1,13+1
• InChIKey: CWVRJTMFETXNAD-VKWJYGAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)(1,2,3-^1^3C₃)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• IUPAC Traditional name: (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)(1,2,3-^1^3C₃)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• Synonyms: (1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-(propenyl-13C3)]oxy]-1,4,5-trihydroxycyclohexanecarboxylic Acid; 3-(3,4-Dihydroxycinnamoyl)quinic Acid-13C3; 3-Caffeoylquinic Acid-13C3; 3-O-(3,4-Dihydroxycinnamoyl)-D-quinic Acid-13C3; 3-O-Caffeoylquinic Acid-13C3; Heriguard-13C3; NSC 407296-13C3; NSC 70861-13C3; [1S-(1α,3β,4α,5α)]-3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-(propenyl-13C3)]oxy]-1,4,5-trihydroxycyclohexanecarboxylic Acid; Chlorogenic Acid-13C3

Database IDs

• PubChem SID: 162258435
• PubChem CID: 71314735

CALCULATED PROPERTIES

• Acid pKa: 3.3338532
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -2.4192955
• LogD (pH = 7.4): -3.6938899
• Log P: -0.26852977
• Molar Refractivity: 83.2347 cm^3
• Polarizability: 32.441044 Å^3
• Polar Surface Area: 164.75 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C366542

A labelled analog of an important intermediate in lignin biosynthesis. It is an antioxidant and an inhibitor of the tumor promoting activity of phorbol ester. It has protective effect against streptozotocin-nicotinamide generated oxidative stress induced

REFERENCES

• Karthikesan, K. et al.: J. Func. Foods, 2, 134 (2010)
• Lincoln, W.M. et al.: Clin. Exp. Phamacol. Physiol., 27, 152 (2010)
• Gamborg, O.L. et al.: Can. J. Biochem., 45, 1451 (2010)