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COCONUT Compound

berberine

CNP0108877.0 · [C20H18NO4]+ · View on COCONUT ↗

2D Structure

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Identifiers

Nameberberine
IUPAC Name16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaene
COCONUT IDCNP0108877.0
CAS2086-83-1, 633-65-8
InChIKeyYBHILYKTIRIUTE-UHFFFAOYSA-N
InChIInChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
SMILESCOC1=CC=C2C=C3C4=CC5=C(C=C4CC[N+]3=CC2=C1OC)OCO5

Properties

Molecular Formula[C20H18NO4]+
Molecular Weight336.37
Exact Mass336.12303
Log P (ALogP)3.10
TPSA40.80
H-Bond Donors / Acceptors0 / 4
Rotatable Bonds2
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.67
NP-likeness1.30

Classification

NP PathwayAlkaloids
NP SuperclassTyrosine alkaloids
NP ClassIsoquinoline alkaloids
Chemical SuperclassAlkaloids and derivatives
Chemical ClassProtoberberine alkaloids and derivatives
Chemical SubclassProtoberberine alkaloids and derivatives

Reported in GR-MAPs Plants

Papaver somniferum as “Papaver somniferum” in COCONUT
Tinospora cordifolia as “Tinospora cordifolia” in COCONUT

References (273)

  1. 10.1002/(SICI)1099-1573(199703)11:2<155::AID-PTR48>3.0.CO;2-9
  2. 10.1002/(SICI)1099-1573(1998)12:1+<S86::AID-PTR259>3.0.CO;2-C
  3. 10.1002/(SICI)1099-1573(199812)12:8<589::AID-PTR347>3.0.CO;2-I
  4. 10.1002/9780470514344.CH14
  5. 10.1002/9780470744307.gat218
  6. 10.1002/JCCS.199700053
  7. 10.1002/JCCS.200400068
  8. 10.1002/JPS.1035
  9. 10.1002/JPS.2600530707
  10. 10.1002/JPS.2600830327
  11. 10.1002/JSSC.200800055
  12. 10.1002/MC.20690
  13. 10.1002/PCA.2800020204
  14. 10.1002/PCA.2800050508
  15. 10.1002/PTR.1108
  16. 10.1002/PTR.1256
  17. 10.1002/PTR.2399
  18. 10.1002/PTR.2438
  19. 10.1002/PTR.2650070406
  20. 10.1002/biuz.19840140514
  21. 10.1002/food.19880321030
  22. 10.1002/fsn3.3317
  23. 10.1002/jssc.200900690
  24. 10.1007/978-1-4614-0560-3_5
  25. 10.1007/BF00233776
  26. 10.1007/BF00241937
  27. 10.1007/BF00269306
  28. 10.1007/BF00269721
  29. 10.1007/BF00272535
  30. 10.1007/BF00272964
  31. 10.1007/BF00398618
  32. 10.1007/BF00564847
  33. 10.1007/BF00564927
  34. 10.1007/BF00565723
  35. 10.1007/BF00565767
  36. 10.1007/BF00568218
  37. 10.1007/BF00568555
  38. 10.1007/BF00574232
  39. 10.1007/BF00574736
  40. 10.1007/BF00574758

Showing 40 of 273. See all references on COCONUT.

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.