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COCONUT Compound

vitexilactone

CNP0139265.1 · C22H34O5 · View on COCONUT ↗

2D Structure

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Identifiers

Namevitexilactone
IUPAC Name[(1~{R},3~{R},4~{R},4~{a}~{S},8~{a}~{S})-4-hydroxy-3,4~{a},8,8-tetramethyl-4-[2-(5-oxo-2~{H}-furan-3-yl)ethyl]decalin-1-yl] acetate
COCONUT IDCNP0139265.1
CAS61263-49-8
InChIKeyFBWWXAGANVJTLU-HEXLTJKYSA-N
InChIInChI=1S/C22H34O5/c1-14-11-17(27-15(2)23)19-20(3,4)8-6-9-21(19,5)22(14,25)10-7-16-12-18(24)26-13-16/h12,14,17,19,25H,6-11,13H2,1-5H3/t14-,17-,19+,21+,22-/m1/s1
SMILESCC(=O)O[C@@H]1C[C@@H](C)[C@](O)(CCC2=CC(=O)OC2)[C@@]2(C)CCCC(C)(C)[C@H]12

Properties

Molecular FormulaC22H34O5
Molecular Weight378.51
Exact Mass378.24062
Log P (ALogP)3.79
TPSA72.83
H-Bond Donors / Acceptors1 / 5
Rotatable Bonds4
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.75
NP-likeness3.54

Classification

NP PathwayTerpenoids
NP SuperclassDiterpenoids
NP ClassLabdane diterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassTerpene lactones

Reported in GR-MAPs Plants

Vitex negundo as “Vitex negundo var. cannabifolia” in COCONUT

References (17)

  1. 10.1002/PTR.2021
  2. 10.1002/ptr.2021
  3. 10.1016/J.BMCL.2013.08.004
  4. 10.1016/S0031-9422(99)00181-8
  5. 10.1016/S0944-7113(00)80058-6
  6. 10.1016/j.bmcl.2013.08.004
  7. 10.1021/NP0105331
  8. 10.1021/NP9902946
  9. 10.1021/np0105331
  10. 10.1021/np300679x
  11. 10.1055/S-2000-8535
  12. 10.1080/10286020310001617165
  13. 10.1248/CPB.24.1668
  14. 10.1248/CPB.34.4829
  15. 10.1248/CPB.49.82
  16. 10.1248/CPB.52.1492
  17. 10.1248/CPB.59.392

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.