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COCONUT Compound

etoposide

CNP0292234.1 · C29H32O13 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

Nameetoposide
IUPAC Name(5~{S},5~{a}~{R},8~{a}~{R},9~{R})-5-[[(2~{R},4~{a}~{R},6~{R},7~{R},8~{R},8~{a}~{S})-7,8-dihydroxy-2-methyl-4,4~{a},6,7,8,8~{a}-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5~{a},6,8~{a},9-tetrahydro-5~{H}-isobenzofuro[5,6-f][1,3]benzodioxol-8-one
COCONUT IDCNP0292234.1
CAS33419-42-0, Etoposide - CAS 33419-42-0, 121471-01-0
InChIKeyVJJPUSNTGOMMGY-MRVIYFEKSA-N
InChIInChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1
SMILESCOC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O

Properties

Molecular FormulaC29H32O13
Molecular Weight588.56
Exact Mass588.18429
Log P (ALogP)1.34
TPSA160.83
H-Bond Donors / Acceptors3 / 13
Rotatable Bonds5
Lipinski's Rule of 5 Violations2
QED Drug-likeness0.43
NP-likeness1.89

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassLignans
NP ClassArylnaphthalene and aryltetralin lignans
Chemical SuperclassLignans, neolignans and related compounds
Chemical ClassLignan lactones
Chemical SubclassPodophyllotoxins

Reported in GR-MAPs Plants

Chrysopogon zizanioides as “Vetiveria zizanioides” in COCONUT
Withania somnifera as “Withania somnifera” in COCONUT
Glycyrrhiza glabra as “Glycyrrhiza glabra” in COCONUT

References (40)

  1. 10.1016/j.bmcl.2016.03.023
  2. 10.1016/j.bmcl.2019.06.003
  3. 10.1021/ACS.JNATPROD.5B00600
  4. 10.1021/ACS.JNATPROD.6B00783
  5. 10.1021/ACS.JNATPROD.7B00190
  6. 10.1021/ACS.JNATPROD.8B00024
  7. 10.1021/ACS.JNATPROD.8B00823
  8. 10.1021/ACS.JNATPROD.9B00142
  9. 10.1021/ACS.JNATPROD.9B00416
  10. 10.1021/NP50079A015
  11. 10.1021/acs.jnatprod.0c00108
  12. 10.1021/acs.jnatprod.5b00492
  13. 10.1021/acs.jnatprod.5b00600
  14. 10.1021/acs.jnatprod.5b00743
  15. 10.1021/acs.jnatprod.5b00954
  16. 10.1021/acs.jnatprod.5b01013
  17. 10.1021/acs.jnatprod.5b01053
  18. 10.1021/acs.jnatprod.6b00140
  19. 10.1021/acs.jnatprod.6b00773
  20. 10.1021/acs.jnatprod.6b00783
  21. 10.1021/acs.jnatprod.6b00941
  22. 10.1021/acs.jnatprod.6b00981
  23. 10.1021/acs.jnatprod.6b01051
  24. 10.1021/acs.jnatprod.7b00190
  25. 10.1021/acs.jnatprod.7b00410
  26. 10.1021/acs.jnatprod.7b00554
  27. 10.1021/acs.jnatprod.8b00024
  28. 10.1021/acs.jnatprod.8b00121
  29. 10.1021/acs.jnatprod.8b00430
  30. 10.1021/acs.jnatprod.8b00665
  31. 10.1021/acs.jnatprod.8b00823
  32. 10.1021/acs.jnatprod.9b00142
  33. 10.1021/acs.jnatprod.9b00416
  34. 10.1021/acs.jnatprod.9b00678
  35. 10.1021/acs.jnatprod.9b00918
  36. 10.1021/np060022k
  37. 10.1021/np3006887
  38. 10.1021/np4008415
  39. 10.1021/np500736b
  40. 10.1021/np50079a015

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.