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COCONUT Compound

LOLIOLIDE

CNP0245641.2 · C11H16O3 · View on COCONUT ↗

2D Structure

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Identifiers

NameLOLIOLIDE
IUPAC Name(6~{S},7~{a}~{R})-6-hydroxy-4,4,7~{a}-trimethyl-6,7-dihydro-5~{H}-benzofuran-2-one
COCONUT IDCNP0245641.2
CAS5989-02-6
InChIKeyXEVQXKKKAVVSMW-WRWORJQWSA-N
InChIInChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11+/m0/s1
SMILESCC1(C)C[C@H](O)C[C@@]2(C)OC(=O)C=C12

Properties

Molecular FormulaC11H16O3
Molecular Weight196.25
Exact Mass196.10994
Log P (ALogP)1.41
TPSA46.53
H-Bond Donors / Acceptors1 / 3
Rotatable Bonds0
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.60
NP-likeness2.98

Classification

NP PathwayTerpenoids
NP SuperclassApocarotenoids
NP ClassApocarotenoids (β-)
Chemical SuperclassOrganoheterocyclic compounds
Chemical ClassDihydrofurans
Chemical SubclassFuranones

Reported in GR-MAPs Plants

Bacopa monnieri as “Bacopa monnieri” in COCONUT
Nicotiana tabacum as “Nicotiana tabacum” in COCONUT

References (134)

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  2. 10.1002/HLCA.200790012
  3. 10.1002/JCCS.199100050
  4. 10.1002/JCCS.199500076
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  12. 10.1007/S10600-007-0133-Y
  13. 10.1007/S10600-009-9361-7
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  16. 10.1016/0031-9422(73)85133-7
  17. 10.1016/0031-9422(88)80289-9
  18. 10.1016/0031-9422(90)83040-8
  19. 10.1016/0031-9422(90)85113-T
  20. 10.1016/0031-9422(90)85370-U
  21. 10.1016/0031-9422(91)84211-A
  22. 10.1016/0031-9422(91)85043-Y
  23. 10.1016/0031-9422(92)80390-Z
  24. 10.1016/0031-9422(92)80452-K
  25. 10.1016/0031-9422(92)83321-O
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  27. 10.1016/0031-9422(93)85294-2
  28. 10.1016/0031-9422(93)85349-V
  29. 10.1016/0031-9422(94)00688-P
  30. 10.1016/0031-9422(94)85042-9
  31. 10.1016/0031-9422(95)00091-K
  32. 10.1016/0031-9422(95)00790-3
  33. 10.1016/0031-9422(95)00942-6
  34. 10.1016/0031-9422(96)00020-9
  35. 10.1016/0031-9422(96)82943-8
  36. 10.1016/J.BMC.2008.09.021
  37. 10.1016/J.BSE.2007.08.016
  38. 10.1016/J.BSE.2015.01.015
  39. 10.1016/J.BSE.2015.09.007
  40. 10.1016/J.FITOTE.2010.07.011

Showing 40 of 134. 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.