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COCONUT Compound

Cynarine

CNP0220934.2 · C25H24O12 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

NameCynarine
IUPAC Name(1~{R},3~{R},4~{S},5~{R})-1,3-bis[[(~{E})-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxy-cyclohexanecarboxylic acid
COCONUT IDCNP0220934.2
CAS30964-13-7, 212891-05-9, 1884-23-7
InChIKeyYDDUMTOHNYZQPO-RVXRWRFUSA-N
InChIInChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
SMILESO=C(/C=C/C1=CC=C(O)C(O)=C1)O[C@@H]1C[C@@](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)(C(=O)O)C[C@@H](O)[C@@H]1O

Properties

Molecular FormulaC25H24O12
Molecular Weight516.46
Exact Mass516.12678
Log P (ALogP)1.03
TPSA211.28
H-Bond Donors / Acceptors7 / 11
Rotatable Bonds7
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.16
NP-likeness1.67

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

Centella asiatica as “Centella asiatica” in COCONUT
Matricaria chamomilla as “Chamomilla recutita; Matricaria chamomilla” in COCONUT
Artemisia annua as “Artemisia annua” in COCONUT
Foeniculum vulgare as “Foeniculum vulgare” in COCONUT

References (37)

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  3. 10.1007/BF02490607
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  8. 10.1016/J.FOODRES.2017.06.052
  9. 10.1016/J.INDCROP.2012.12.022
  10. 10.1016/J.PHYMED.2007.01.010
  11. 10.1016/J.PHYTOCHEM.2013.07.003
  12. 10.1016/S0021-9673(01)92486-0
  13. 10.1016/S0031-9422(00)81260-1
  14. 10.1016/S0031-9422(98)00084-3
  15. 10.1016/S0305-1978(02)00029-7
  16. 10.1016/S0731-7085(00)00264-8
  17. 10.1016/S0944-7113(96)80041-9
  18. 10.1016/j.phytochem.2013.07.003
  19. 10.1021/JF001331Y
  20. 10.1021/JF011439T
  21. 10.1021/JF030813H
  22. 10.1021/JF061687V
  23. 10.1021/acs.jnatprod.6b01026
  24. 10.1021/jf500926v
  25. 10.1021/np50052a004
  26. 10.1055/S-2002-32561
  27. 10.1055/S-2002-34417
  28. 10.1055/S-2006-960413
  29. 10.1055/S-2008-1034316
  30. 10.1080/09637486.2017.1418845
  31. 10.1080/10286020903482810
  32. 10.1080/13880200500408491
  33. 10.1081/JLC-200028369
  34. 10.1211/0022357011776009
  35. 10.1248/BPB.30.935
  36. 10.1248/CPB.49.915
  37. 10.4268/CJCMM20142423

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.