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COCONUT Compound

Lutein 5,6-epoxide

CNP0224108.1 · C40H56O3 · View on COCONUT ↗

2D Structure

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Identifiers

NameLutein 5,6-epoxide
IUPAC Name(1~{R},3~{S},6~{S})-6-[(1~{E},3~{E},5~{E},7~{E},9~{E},11~{E},13~{E},15~{E},17~{E})-18-[(1~{R},4~{R})-4-hydroxy-2,6,6-trimethyl-cyclohex-2-en-1-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
COCONUT IDCNP0224108.1
CAS28368-08-3
InChIKeyDYUUPIKEWLHQGQ-FJOIUHRLSA-N
InChIInChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-25,34-36,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35-,36-,39+,40-/m0/s1
SMILESCC1=C[C@H](O)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C

Properties

Molecular FormulaC40H56O3
Molecular Weight584.89
Exact Mass584.42295
Log P (ALogP)9.61
TPSA52.99
H-Bond Donors / Acceptors2 / 3
Rotatable Bonds10
Lipinski's Rule of 5 Violations2
QED Drug-likeness0.15
NP-likeness2.36

Classification

NP PathwayTerpenoids
NP SuperclassCarotenoids (C40)
NP ClassCarotenoids (C40, β-ε)
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassTetraterpenoids

Reported in GR-MAPs Plants

Oryza sativa as “Oryza Sativa” in COCONUT

References (34)

  1. 10.1002/HLCA.19470300508
  2. 10.1002/HLCA.19470300643
  3. 10.1002/HLCA.19760590440
  4. 10.1002/JMS.1794
  5. 10.1002/fedr.19911020518
  6. 10.1002/fedr.19921030316
  7. 10.1007/BF00597870
  8. 10.1007/BF00598698
  9. 10.1007/BF00607557
  10. 10.1007/bf02862326
  11. 10.1016/0305-0491(84)90180-9
  12. 10.1016/0305-1978(75)90058-7
  13. 10.1016/0305-1978(85)90030-4
  14. 10.1016/0305-1978(85)90064-X
  15. 10.1016/0305-1978(87)90002-0
  16. 10.1016/0305-1978(87)90003-2
  17. 10.1016/0305-1978(88)90082-8
  18. 10.1016/J.PHYTOCHEM.2006.02.002
  19. 10.1016/S0031-9422(00)80801-8
  20. 10.1016/S0031-9422(00)83753-X
  21. 10.1016/S0031-9422(00)94529-1
  22. 10.1016/j.phytochem.2006.02.002
  23. 10.1021/JF00011A003
  24. 10.1021/JF00059A016
  25. 10.1021/JF980823W
  26. 10.1023/a:1008173807143
  27. 10.1038/hortres.2015.36
  28. 10.1086/332998
  29. 10.1093/treephys/27.10.1407
  30. 10.1104/pp.91.1.190
  31. 10.1111/J.1365-2621.1989.TB04709.X
  32. 10.1111/J.1365-2621.2001.TB15182.X
  33. 10.1515/BCHM2.1958.310.1.50
  34. 10.1515/znb-1969-0724

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.