|
Menu

COCONUT Compound

8-Prenylnaringenin

CNP0273317.1 · C20H20O5 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

Name8-Prenylnaringenin
IUPAC Name(2~{S})-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chroman-4-one
COCONUT IDCNP0273317.1
CAS53846-50-7
InChIKeyLPEPZZAVFJPLNZ-SFHVURJKSA-N
InChIInChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3/t18-/m0/s1
SMILESCC(C)=CCC1=C(O)C=C(O)C2=C1O[C@H](C1=CC=C(O)C=C1)CC2=O

Properties

Molecular FormulaC20H20O5
Molecular Weight340.38
Exact Mass340.13107
Log P (ALogP)4.02
TPSA86.99
H-Bond Donors / Acceptors3 / 5
Rotatable Bonds3
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.73
NP-likeness2.20

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassFlavonoids
NP ClassFlavanones
Chemical SuperclassPhenylpropanoids and polyketides
Chemical ClassFlavonoids
Chemical SubclassFlavans

Reported in GR-MAPs Plants

Azadirachta indica as “Azadirachta indica” in COCONUT
Glycyrrhiza glabra as “Glycyrrhiza glabra” in COCONUT

References (40)

  1. 10.1002/PTR.2286
  2. 10.1002/cbdv.201300266
  3. 10.1007/BF02490811
  4. 10.1007/S11095-006-9902-8
  5. 10.1016/0031-9422(88)80041-4
  6. 10.1016/0031-9422(89)80041-X
  7. 10.1016/0031-9422(94)00971-U
  8. 10.1016/J.JEP.2008.01.011
  9. 10.1016/J.JEP.2009.06.018
  10. 10.1016/J.JSBMB.2005.04.038
  11. 10.1016/J.JSBMB.2006.11.026
  12. 10.1016/J.PHYTOCHEM.2004.05.009
  13. 10.1016/J.PHYTOCHEM.2009.05.007
  14. 10.1016/S0031-9422(00)00005-4
  15. 10.1016/S0031-9422(00)80458-6
  16. 10.1016/S0031-9422(00)81081-X
  17. 10.1016/S0031-9422(00)81244-3
  18. 10.1016/S0031-9422(00)84740-8
  19. 10.1016/S0031-9422(02)00378-3
  20. 10.1016/S0031-9422(02)00671-4
  21. 10.1016/S0031-9422(96)00744-3
  22. 10.1016/S0031-9422(97)00474-3
  23. 10.1016/S0040-4020(02)00296-X
  24. 10.1016/j.bmcl.2018.09.003
  25. 10.1016/s0305-1978(97)00062-8
  26. 10.1021/JF034666Z
  27. 10.1021/JF050448P
  28. 10.1021/NP000406P
  29. 10.1021/NP049783I
  30. 10.1021/NP50102A033
  31. 10.1021/acs.jnatprod.5b01052
  32. 10.1021/acs.jnatprod.7b01070
  33. 10.1021/np100797y
  34. 10.1124/dmd.32.2.272
  35. 10.1177/1934578X1000501210
  36. 10.1210/JC.84.6.2249
  37. 10.1248/CPB.26.3863
  38. 10.1248/CPB.36.2220
  39. 10.1248/CPB.51.1147
  40. 10.2903/j.efsa.2012.2663

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.