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COCONUT Compound

(+)-lyoniresinol

CNP0153696.1 · C22H28O8 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

Name(+)-lyoniresinol
IUPAC Name(2~{R},3~{R},4~{S})-4-(4-hydroxy-3,5-dimethoxy-phenyl)-2,3-bis(hydroxymethyl)-5,7-dimethoxy-tetralin-6-ol
COCONUT IDCNP0153696.1
CAS14464-90-5
InChIKeyZDVZKBOFCHOPLM-SUNYJGFJSA-N
InChIInChI=1S/C22H28O8/c1-27-15-7-12(8-16(28-2)20(15)25)18-14(10-24)13(9-23)5-11-6-17(29-3)21(26)22(30-4)19(11)18/h6-8,13-14,18,23-26H,5,9-10H2,1-4H3/t13-,14-,18+/m0/s1
SMILESCOC1=CC([C@H]2C3=C(OC)C(O)=C(OC)C=C3C[C@@H](CO)[C@@H]2CO)=CC(OC)=C1O

Properties

Molecular FormulaC22H28O8
Molecular Weight420.46
Exact Mass420.17842
Log P (ALogP)2.04
TPSA117.84
H-Bond Donors / Acceptors4 / 8
Rotatable Bonds7
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.54
NP-likeness1.69

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassLignans
NP ClassArylnaphthalene and aryltetralin lignans
Chemical SuperclassLignans, neolignans and related compounds
Chemical ClassAryltetralin lignans
Chemical Subclass9,9p-dihydroxyaryltetralin lignans

Reported in GR-MAPs Plants

Vitex negundo as “Vitex negundo” in COCONUT

References (27)

  1. 10.1002/CHIN.200407160
  2. 10.1002/PTR.2443
  3. 10.1016/0031-9422(88)83069-3
  4. 10.1016/J.BMCL.2011.02.104
  5. 10.1016/J.PHYMED.2004.09.001
  6. 10.1016/S0031-9422(02)00018-3
  7. 10.1016/S0031-9422(03)00422-9
  8. 10.1016/S0031-9422(96)00645-0
  9. 10.1016/S0031-9422(96)00879-5
  10. 10.1016/j.bmcl.2011.02.104
  11. 10.1016/j.bse.2014.04.016
  12. 10.1021/NP0301543
  13. 10.1021/NP200117Y
  14. 10.1021/NP2001896
  15. 10.1021/NP50066A025
  16. 10.1021/np0301543
  17. 10.1021/np200117y
  18. 10.1021/np2001896
  19. 10.1055/S-2008-1034318
  20. 10.1248/BPB.23.1328
  21. 10.1248/CPB.49.785
  22. 10.1248/CPB.51.1051
  23. 10.1248/CPB.53.641
  24. 10.1248/CPB.57.487
  25. 10.1248/YAKUSHI1947.116.12_911
  26. 10.3390/11121009
  27. 10.3390/MOLECULES13081923

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.