|
Menu

COCONUT Compound

12a-Hydroxyrotenone

CNP0205624.3 · C23H22O7 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

Name12a-Hydroxyrotenone
IUPAC Name(1~{R},6~{R},13~{R})-13-hydroxy-6-isopropenyl-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
COCONUT IDCNP0205624.3
InChIKeyJFVKWCYZKMUTLH-AYPBNUJASA-N
InChIInChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1
SMILESC=C(C)[C@H]1CC2=C(C=CC3=C2O[C@@H]2COC4=CC(OC)=C(OC)C=C4[C@]2(O)C3=O)O1

Properties

Molecular FormulaC23H22O7
Molecular Weight410.42
Exact Mass410.13655
Log P (ALogP)2.81
TPSA83.45
H-Bond Donors / Acceptors1 / 7
Rotatable Bonds3
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.78
NP-likeness2.18

Classification

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

Reported in GR-MAPs Plants

Tephrosia purpurea as “Tephrosia Purpurea” in COCONUT

References (32)

  1. 10.1002/(SICI)1521-4168(19980901)21:9<513::AID-JHRC513>3.0.CO,2-F
  2. 10.1002/(SICI)1521-4168(19980901)21:9<513::AID-JHRC513>3.0.CO;2-F
  3. 10.1002/(sici)1521-4168(19980901)21:9<513::aid-jhrc513>3.0.co;2-f
  4. 10.1002/PTR.889
  5. 10.1016/0031-9422(80)87050-6
  6. 10.1016/0031-9422(82)80103-9
  7. 10.1016/0031-9422(89)80308-5
  8. 10.1016/0031-9422(90)85212-X
  9. 10.1016/0031-9422(96)00134-3
  10. 10.1016/S0031-9422(00)90838-0
  11. 10.1016/S0031-9422(82)85084-X
  12. 10.1016/j.bmc.2006.09.024
  13. 10.1021/JF981188X
  14. 10.1021/NP010126P
  15. 10.1021/NP0303815
  16. 10.1021/NP0303815.S001
  17. 10.1021/NP100430R
  18. 10.1021/NP100763P
  19. 10.1021/NP50051A002
  20. 10.1021/NP50055A035
  21. 10.1021/np010126p
  22. 10.1021/np0303815
  23. 10.1021/np100430r
  24. 10.1021/np100763p
  25. 10.1021/np400567c
  26. 10.1055/S-2005-864182
  27. 10.1073/PNAS.95.7.3380
  28. 10.1093/CHROMSCI/38.4.174
  29. 10.1139/V07-120
  30. 10.1248/CPB.50.534
  31. 10.1248/CPB.54.1530
  32. 10.3987/COM-92-6288

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.