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COCONUT Compound

ISODIOSPYRIN

CNP0265954.0 · C22H14O6 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

NameISODIOSPYRIN
IUPAC Name5-hydroxy-6-(4-hydroxy-2-methyl-5,8-dioxo-1-naphthyl)-7-methyl-naphthalene-1,4-dione
COCONUT IDCNP0265954.0
CAS20175-84-2, 89475-33-2
InChIKeyOEEOHKZVBKYMBA-UHFFFAOYSA-N
InChIInChI=1S/C22H14O6/c1-9-7-11-12(23)3-4-13(24)19(11)22(28)18(9)17-10(2)8-16(27)20-14(25)5-6-15(26)21(17)20/h3-8,27-28H,1-2H3
SMILESCC1=CC2=C(C(=O)C=CC2=O)C(O)=C1C1=C(C)C=C(O)C2=C1C(=O)C=CC2=O

Properties

Molecular FormulaC22H14O6
Molecular Weight374.35
Exact Mass374.07904
Log P (ALogP)3.25
TPSA108.74
H-Bond Donors / Acceptors2 / 6
Rotatable Bonds1
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.79
NP-likeness1.32

Classification

NP PathwayPolyketides
NP SuperclassNaphthalenes
NP ClassNaphthoquinones
Chemical SuperclassBenzenoids
Chemical ClassNaphthalenes
Chemical SubclassNaphthoquinones

Reported in GR-MAPs Plants

Nepeta cataria as “Nepeta cataria” in COCONUT

References (31)

  1. 10.1002/(SICI)1099-1573(199805)12:3<155::AID-PTR214>3.0.CO;2-1
  2. 10.1002/(SICI)1099-1573(200003)14:2<112::AID-PTR488>3.0.CO;2-T
  3. 10.1002/CBDV.201000310
  4. 10.1002/CHIN.200640213
  5. 10.1016/0031-9422(81)83034-8
  6. 10.1016/0165-1218(83)90182-9
  7. 10.1016/0378-8741(88)90006-2
  8. 10.1016/J.PHYTOCHEM.2004.03.011
  9. 10.1016/J.SAJB.2005.09.009
  10. 10.1016/S0021-9673(01)87659-7
  11. 10.1016/S0031-9422(00)80490-2
  12. 10.1016/S0031-9422(00)82610-2
  13. 10.1016/S0031-9422(00)83757-7
  14. 10.1016/S0031-9422(00)83864-9
  15. 10.1016/S0031-9422(00)84643-9
  16. 10.1016/S0031-9422(00)97787-2
  17. 10.1016/S0031-9422(97)00398-1
  18. 10.1016/S0031-9422(97)01020-0
  19. 10.1016/j.sajb.2005.09.009
  20. 10.1021/JF60218A018
  21. 10.1039/J39680002279
  22. 10.1055/S-2006-957464
  23. 10.1055/S-2006-957703
  24. 10.1055/S-2006-962783
  25. 10.1055/S-2007-969969
  26. 10.1055/s-2006-957703
  27. 10.1080/10286020500478815
  28. 10.1248/CPB.19.2308
  29. 10.1248/CPB.19.2314
  30. 10.1248/CPB.20.2029
  31. 10.1248/CPB.57.532

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.