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COCONUT Compound

alpha-Toxicarol

CNP0306395.1 · C23H22O7 · View on COCONUT ↗

2D Structure

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Identifiers

Namealpha-Toxicarol
IUPAC Name(1~{S},14~{S})-11-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3,5,9,11,15(20),16,18-heptaen-13-one
COCONUT IDCNP0306395.1
CAS82-09-7
InChIKeyJLTNCZQNGBLBGO-MOPGFXCFSA-N
InChIInChI=1S/C23H22O7/c1-23(2)6-5-11-15(30-23)8-13(24)20-21(25)19-12-7-16(26-3)17(27-4)9-14(12)28-10-18(19)29-22(11)20/h5-9,18-19,24H,10H2,1-4H3/t18-,19+/m1/s1
SMILESCOC1=CC2=C(C=C1OC)[C@@H]1C(=O)C3=C(O)C=C4OC(C)(C)C=CC4=C3O[C@@H]1CO2

Properties

Molecular FormulaC23H22O7
Molecular Weight410.42
Exact Mass410.13655
Log P (ALogP)3.71
TPSA83.45
H-Bond Donors / Acceptors1 / 7
Rotatable Bonds2
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.81
NP-likeness2.60

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassIsoflavonoids
NP ClassIsoflavanones
Chemical SuperclassPhenylpropanoids and polyketides
Chemical ClassIsoflavonoids
Chemical SubclassRotenoids

Reported in GR-MAPs Plants

Tephrosia purpurea as “Tephrosia purpurea” in COCONUT

References (19)

  1. 10.1002/RECL.19390580304
  2. 10.1016/0031-9422(85)80019-4
  3. 10.1016/0031-9422(89)80308-5
  4. 10.1016/J.PHYTOCHEM.2005.02.005
  5. 10.1016/S0031-9422(00)80597-X
  6. 10.1016/S0031-9422(97)00405-6
  7. 10.1016/S0031-9422(97)80029-5
  8. 10.1016/j.phytochem.2012.02.025
  9. 10.1021/NP010126P
  10. 10.1021/NP0302100
  11. 10.1021/NP030554Q
  12. 10.1021/acs.jnatprod.6b00809
  13. 10.1021/np010126p
  14. 10.1039/JR9400001178
  15. 10.1055/S-2004-815447
  16. 10.1073/PNAS.95.7.3380
  17. 10.1139/V07-120
  18. 10.1248/CPB.56.835
  19. 10.1515/ZNC-2002-7-805

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.