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COCONUT Compound

2-Coumaroylquinic acid

CNP0215883.1 · C16H18O8 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

Name2-Coumaroylquinic acid
IUPAC Name(1~{S},3~{R},4~{R},5~{R})-1,3,4-trihydroxy-5-[(~{E})-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexanecarboxylic acid
COCONUT IDCNP0215883.1
CAS1899-30-5, 5746-55-4
InChIKeyBMRSEYFENKXDIS-OTCYKTEZSA-N
InChIInChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14-,16+/m1/s1
SMILESO=C(/C=C/C1=CC=C(O)C=C1)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](O)[C@H]1O

Properties

Molecular FormulaC16H18O8
Molecular Weight338.31
Exact Mass338.10017
Log P (ALogP)-0.35
TPSA144.52
H-Bond Donors / Acceptors5 / 7
Rotatable Bonds4
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.37
NP-likeness2.15

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassPhenylpropanoids (C6-C3)
NP ClassCinnamic acids and derivatives
Chemical SuperclassOrganic oxygen compounds
Chemical ClassOrganooxygen compounds
Chemical SubclassAlcohols and polyols

Reported in GR-MAPs Plants

Daucus carota as “Daucus carota” in COCONUT

References (24)

  1. 10.1002/PCA.1259
  2. 10.1002/PRAC.19923340405
  3. 10.1002/RCM.3166
  4. 10.1007/S11418-007-0139-6
  5. 10.1016/0031-9422(83)83029-5
  6. 10.1016/J.BMCL.2007.10.046
  7. 10.1016/J.FCT.2012.04.034
  8. 10.1016/J.FOODCHEM.2009.04.098
  9. 10.1016/J.PHYTOCHEM.2006.11.026
  10. 10.1016/J.PHYTOCHEM.2008.03.003
  11. 10.1016/J.PHYTOCHEM.2013.04.005
  12. 10.1016/J.PHYTOCHEM.2013.07.003
  13. 10.1016/J.POSTHARVBIO.2018.05.012
  14. 10.1016/J.TALANTA.2012.11.012
  15. 10.1016/J.TET.2006.09.020
  16. 10.1016/S0031-9422(00)00143-6
  17. 10.1016/S0031-9422(00)80722-0
  18. 10.1016/S0031-9422(00)81102-4
  19. 10.1016/S0031-9422(00)95107-0
  20. 10.1016/S0031-9422(02)00055-9
  21. 10.1016/j.phytochem.2013.04.005
  22. 10.1016/j.phytochem.2013.07.003
  23. 10.1021/JF0734727
  24. 10.1021/JF900625R

Data from COCONUT (COlleCtion of Open Natural prodUcTs), released under CC0. Chandrasekhar V. et al. COCONUT 2.0: a comprehensive overhaul and curation of the collection of open natural products database. Nucleic Acids Research (2024), doi:10.1093/nar/gkae1063. COCONUT release 2026-10.