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COCONUT Compound

Yohimbine

CNP0305326.1 · C21H26N2O3 · View on COCONUT ↗

2D Structure

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Identifiers

NameYohimbine
IUPAC Namemethyl (1~{S},15~{R},18~{S},19~{R},20~{S})-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
COCONUT IDCNP0305326.1
CAS146-48-5, 103834-06-6
InChIKeyBLGXFZZNTVWLAY-SCYLSFHTSA-N
InChIInChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1
SMILESCOC(=O)[C@@H]1[C@H]2C[C@H]3C4=C(CCN3C[C@@H]2CC[C@@H]1O)C1=CC=CC=C1N4

Properties

Molecular FormulaC21H26N2O3
Molecular Weight354.45
Exact Mass354.19434
Log P (ALogP)2.65
TPSA65.56
H-Bond Donors / Acceptors2 / 4
Rotatable Bonds1
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.77
NP-likeness1.17

Classification

NP PathwayAlkaloids
NP SuperclassTryptophan alkaloids
NP ClassYohimbine-like alkaloids
Chemical SuperclassAlkaloids and derivatives
Chemical ClassCorynanthean-type alkaloids
Chemical SubclassCorynanthean-type alkaloids

Reported in GR-MAPs Plants

Catharanthus roseus as “Catharanthus roseus” in COCONUT
Rauvolfia serpentina as “Rauvolfia Serpentina; Rauwolfia serpentina” in COCONUT

References (54)

  1. 10.1002/CHIN.198107333
  2. 10.1002/HLCA.19590420331
  3. 10.1002/HLCA.19670500129
  4. 10.1002/HLCA.19800630714
  5. 10.1002/HLCA.19810640615
  6. 10.1002/JPS.2600521126
  7. 10.1002/JPS.2600531238
  8. 10.1002/JPS.2600570629
  9. 10.1002/PCA.567
  10. 10.1002/PCA.699
  11. 10.1002/PTR.2650040203
  12. 10.1002/RCM.8037
  13. 10.1002/RECL.19640830206
  14. 10.1007/BF00267656
  15. 10.1007/BF02151532
  16. 10.1007/S13659-011-0023-7
  17. 10.1016/0031-9422(75)85309-X
  18. 10.1016/0031-9422(88)83053-X
  19. 10.1016/0031-9422(91)80111-D
  20. 10.1016/0031-9422(91)84183-S
  21. 10.1016/0031-9422(92)80356-J
  22. 10.1016/0031-9422(92)83311-L
  23. 10.1016/0378-8741(81)90022-2
  24. 10.1016/0378-8741(84)90046-1
  25. 10.1016/0378-8741(84)90099-0
  26. 10.1016/J.EJMECH.2020.112960
  27. 10.1016/S0021-9673(01)88452-1
  28. 10.1016/S0031-9422(00)80165-X
  29. 10.1016/S0031-9422(00)90527-2
  30. 10.1016/S0031-9422(97)00302-6
  31. 10.1016/S0040-4020(01)88602-6
  32. 10.1017/S0022149X00033812
  33. 10.1017/s0022149x00033812
  34. 10.1021/NP50009A016
  35. 10.1021/NP50017A004
  36. 10.1021/NP50029A018
  37. 10.1021/NP50053A016
  38. 10.1021/np058007n
  39. 10.1055/S-0028-1097468
  40. 10.1055/S-0028-1097576

Showing 40 of 54. 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.