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COCONUT Compound

Secoisolariciresinol

CNP0283362.3 · C20H26O6 · View on COCONUT ↗

2D Structure

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Identifiers

NameSecoisolariciresinol
IUPAC Name(2~{R},3~{R})-2,3-bis[(4-hydroxy-3-methoxy-phenyl)methyl]butane-1,4-diol
COCONUT IDCNP0283362.3
CAS29388-59-8
InChIKeyPUETUDUXMCLALY-HOTGVXAUSA-N
InChIInChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1
SMILESCOC1=CC(C[C@@H](CO)[C@H](CO)CC2=CC=C(O)C(OC)=C2)=CC=C1O

Properties

Molecular FormulaC20H26O6
Molecular Weight362.42
Exact Mass362.17294
Log P (ALogP)2.12
TPSA99.38
H-Bond Donors / Acceptors4 / 6
Rotatable Bonds9
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.55
NP-likeness0.77

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassLignans
NP ClassDibenzylbutane lignans
Chemical SuperclassLignans, neolignans and related compounds
Chemical ClassDibenzylbutane lignans
Chemical SubclassDibenzylbutane lignans

Reported in GR-MAPs Plants

Ocimum basilicum as “Ocimum basilicum” in COCONUT
Foeniculum vulgare as “Foeniculum vulgare” in COCONUT
Daucus carota as “Daucus carota” in COCONUT
Origanum vulgare as “Origanum vulgare” in COCONUT
Solanum lycopersicum as “Solanum lycopersicum” in COCONUT

References (69)

  1. 10.1002/CHIN.200844208
  2. 10.1002/HLCA.200590212
  3. 10.1002/hlca.200590212
  4. 10.1007/S00425-011-1492-Y
  5. 10.1016/0031-9422(92)80374-N
  6. 10.1016/0031-9422(93)85117-A
  7. 10.1016/J.BMC.2003.09.010
  8. 10.1016/J.BMC.2008.06.032
  9. 10.1016/J.BMCL.2011.02.104
  10. 10.1016/J.FOODCHEM.2009.03.002
  11. 10.1016/J.FOODCHEM.2012.03.133
  12. 10.1016/J.PHYTOCHEM.2005.04.026
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  15. 10.1016/S0031-9422(00)00126-6
  16. 10.1016/S0031-9422(00)89347-4
  17. 10.1016/S0031-9422(00)90485-0
  18. 10.1016/S0031-9422(01)00429-0
  19. 10.1016/S0308-8146(03)00222-X
  20. 10.1016/j.bmc.2008.06.032
  21. 10.1016/j.bmcl.2011.02.104
  22. 10.1016/s0031-9422(00)89347-4
  23. 10.1021/JF034644C
  24. 10.1021/JF051488W
  25. 10.1021/JF800476R
  26. 10.1021/NP000307B
  27. 10.1021/NP0301083
  28. 10.1021/NP040219H
  29. 10.1021/NP050001A
  30. 10.1021/NP058022S
  31. 10.1021/NP058036Y
  32. 10.1021/NP100665J
  33. 10.1021/NP2002918
  34. 10.1021/NP8004166
  35. 10.1021/NP8006342
  36. 10.1021/NP9006298
  37. 10.1021/jf034644c
  38. 10.1021/np000307b
  39. 10.1021/np020235j
  40. 10.1021/np058036y

Showing 40 of 69. See all references on COCONUT.

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.