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COCONUT Compound

Marrubiin

CNP0107084.1 · C20H28O4 · View on COCONUT ↗

2D Structure

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Identifiers

NameMarrubiin
IUPAC Name(1~{R},4~{S},8~{S},9~{R},10~{R},12~{R})-9-[2-(3-furyl)ethyl]-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-3-one
COCONUT IDCNP0107084.1
CAS465-92-9
InChIKeyHQLLRHCTVDVUJB-OBHOOXMTSA-N
InChIInChI=1S/C20H28O4/c1-13-11-15-16-18(2,17(21)24-15)7-4-8-19(16,3)20(13,22)9-5-14-6-10-23-12-14/h6,10,12-13,15-16,22H,4-5,7-9,11H2,1-3H3/t13-,15-,16+,18+,19+,20-/m1/s1
SMILESC[C@@H]1C[C@H]2OC(=O)[C@@]3(C)CCC[C@@](C)([C@@H]23)[C@@]1(O)CCC1=COC=C1

Properties

Molecular FormulaC20H28O4
Molecular Weight332.44
Exact Mass332.19876
Log P (ALogP)3.72
TPSA59.67
H-Bond Donors / Acceptors1 / 4
Rotatable Bonds3
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.86
NP-likeness3.20

Classification

NP PathwayTerpenoids
NP SuperclassDiterpenoids
NP ClassLabdane diterpenoids
Chemical SuperclassOrganoheterocyclic compounds
Chemical ClassLactones
Chemical SubclassGamma butyrolactones

Reported in GR-MAPs Plants

Nepeta cataria as “Nepeta cataria” in COCONUT

References (25)

  1. 10.1002/9780470744307.gat218
  2. 10.1002/JPS.2600530810
  3. 10.1002/JPS.3080190307
  4. 10.1002/MRC.1136
  5. 10.1002/biuz.19840140514
  6. 10.1007/BF00569805
  7. 10.1007/BF01373788
  8. 10.1016/0021-9673(92)85036-S
  9. 10.1016/J.FARMAC.2005.01.003
  10. 10.1016/J.JEP.2006.05.023
  11. 10.1016/J.JEP.2011.08.041
  12. 10.1016/J.PHYMED.2011.12.008
  13. 10.1016/J.PHYTOCHEM.2005.02.029
  14. 10.1016/S0305-1978(01)00148-X
  15. 10.1016/S0944-7113(00)80082-3
  16. 10.1016/S0944-7113(98)80005-6
  17. 10.1016/j.jep.2006.05.023
  18. 10.1016/j.jep.2011.08.041
  19. 10.1039/JR9390000587
  20. 10.1042/BJ3260449
  21. 10.1055/S-2003-37042
  22. 10.1055/S-2006-957451
  23. 10.1055/s-2003-37042
  24. 10.1111/J.2042-7158.2011.01321.X
  25. 10.1248/CPB.48.1234

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.