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COCONUT Compound

Coclaurine

CNP0183208.2 · C17H19NO3 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

NameCoclaurine
IUPAC Name(1~{S})-1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
COCONUT IDCNP0183208.2
CAS486-39-5
InChIKeyLVVKXRQZSRUVPY-HNNXBMFYSA-N
InChIInChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3/t15-/m0/s1
SMILESCOC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O)C=C1)NCC2

Properties

Molecular FormulaC17H19NO3
Molecular Weight285.34
Exact Mass285.13649
Log P (ALogP)2.54
TPSA61.72
H-Bond Donors / Acceptors3 / 4
Rotatable Bonds3
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.81
NP-likeness1.36

Classification

NP PathwayAlkaloids
NP SuperclassTyrosine alkaloids
NP ClassIsoquinoline alkaloids
Chemical SuperclassOrganoheterocyclic compounds
Chemical ClassIsoquinolines and derivatives
Chemical SubclassBenzylisoquinolines

Reported in GR-MAPs Plants

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

References (47)

  1. 10.1007/BF00565157
  2. 10.1007/BF00575052
  3. 10.1007/BF00576235
  4. 10.1007/BF00579424
  5. 10.1007/BF02857740
  6. 10.1007/BF02911058
  7. 10.1007/S10600-011-9921-5
  8. 10.1007/S12272-009-1111-7
  9. 10.1016/0031-9422(83)80048-X
  10. 10.1016/0031-9422(90)85344-F
  11. 10.1016/0040-4020(80)88040-9
  12. 10.1016/J.PHYTOCHEM.2003.12.010
  13. 10.1016/J.PHYTOCHEM.2004.03.017
  14. 10.1016/J.PHYTOCHEM.2006.07.011
  15. 10.1016/S0031-9422(98)00745-6
  16. 10.1016/S0031-9422(99)00230-7
  17. 10.1016/S0305-1978(02)00024-8
  18. 10.1021/NP000061A
  19. 10.1021/NP000373D
  20. 10.1021/NP010035S
  21. 10.1021/NP0105578
  22. 10.1021/NP050082A
  23. 10.1021/NP200700F
  24. 10.1021/NP50004A007
  25. 10.1021/NP50014A005
  26. 10.1021/NP50033A010
  27. 10.1021/NP50064A031
  28. 10.1021/NP50101A020
  29. 10.1021/NP960037Q
  30. 10.1021/NP960195H
  31. 10.1021/NP960371M
  32. 10.1021/np50124a001
  33. 10.1055/S-0028-1097904
  34. 10.1055/S-2007-969081
  35. 10.1055/S-2007-969493
  36. 10.1071/CH9810195
  37. 10.1071/ch9671729
  38. 10.1071/ch9810195
  39. 10.1074/JBC.M106405200
  40. 10.1074/JBC.M116.747261

Showing 40 of 47. 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.