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COCONUT Compound

Obacunone

CNP0233253.5 · C26H30O7 · View on COCONUT ↗

2D Structure

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Identifiers

NameObacunone
IUPAC Name(1~{R},2~{R},4~{S},7~{S},8~{S},11~{R},12~{R},18~{R})-7-(3-furyl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icos-13-ene-5,15,20-trione
COCONUT IDCNP0233253.5
InChIKeyMAYJEFRPIKEYBL-OASIGRBWSA-N
InChIInChI=1S/C26H30O7/c1-22(2)16-12-17(27)25(5)15(23(16,3)9-7-18(28)32-22)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)33-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3/t15-,16+,19+,20-,23-,24+,25+,26-/m1/s1
SMILESCC1(C)OC(=O)C=C[C@]2(C)[C@H]3CC[C@@]4(C)[C@H](C5=COC=C5)OC(=O)[C@H]5O[C@]54[C@]3(C)C(=O)C[C@@H]12

Properties

Molecular FormulaC26H30O7
Molecular Weight454.52
Exact Mass454.19915
Log P (ALogP)3.92
TPSA95.34
H-Bond Donors / Acceptors0 / 7
Rotatable Bonds1
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.47
NP-likeness3.23

Classification

NP PathwayTerpenoids
NP SuperclassTriterpenoids
NP ClassLimonoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassTriterpenoids

Reported in GR-MAPs Plants

Salvia officinalis as “Salvia officinalis” in COCONUT

References (45)

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  2. 10.1002/JSSC.201400012
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  4. 10.1016/0021-9673(93)80266-B
  5. 10.1016/0031-9422(82)85227-8
  6. 10.1016/0031-9422(88)84129-3
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  8. 10.1016/0305-1978(95)00109-3
  9. 10.1016/J.BMCL.2013.04.064
  10. 10.1016/J.JPBA.2019.03.056
  11. 10.1016/S0031-9422(00)81459-4
  12. 10.1016/S0031-9422(00)84692-0
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  14. 10.1016/S0031-9422(00)97551-4
  15. 10.1016/S0031-9422(96)00589-4
  16. 10.1016/S0031-9422(97)00541-4
  17. 10.1016/S0031-9422(97)00542-6
  18. 10.1016/S0031-9422(98)00519-6
  19. 10.1016/S0031-9422(99)00096-5
  20. 10.1016/j.bmcl.2013.04.064
  21. 10.1021/JF00088A003
  22. 10.1021/JF60231A016
  23. 10.1021/NP070588O
  24. 10.1021/NP50019A002
  25. 10.1021/NP50064A040
  26. 10.1021/NP970201P
  27. 10.1021/np070588o
  28. 10.1039/CT9119901993
  29. 10.1055/S-0029-1243113
  30. 10.1080/00387019608007063
  31. 10.1111/J.1365-2621.1995.TB04574.X
  32. 10.1248/CPB.36.4453
  33. 10.1248/CPB.38.2332
  34. 10.1248/CPB.49.649
  35. 10.1248/CPB.56.102
  36. 10.1248/YAKUSHI1881.1927.550_1035
  37. 10.1248/YAKUSHI1881.55.10_1153
  38. 10.1248/YAKUSHI1947.105.8_742
  39. 10.1271/BBB1961.53.2635
  40. 10.1515/ZNC-2003-3-403

Showing 40 of 45. 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.