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COCONUT Compound

Pubescine

CNP0228098.1 · C22H26N2O4 · View on COCONUT ↗

2D Structure

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Identifiers

NamePubescine
IUPAC Namemethyl (1~{S},15~{S},16~{S},20~{S})-6-methoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
COCONUT IDCNP0228098.1
CAS482-96-2
InChIKeyKXEMQEGRZWUKJS-RURTYGRKSA-N
InChIInChI=1S/C22H26N2O4/c1-12-17-10-24-7-6-15-14-5-4-13(26-2)8-19(14)23-21(15)20(24)9-16(17)18(11-28-12)22(25)27-3/h4-5,8,11-12,16-17,20,23H,6-7,9-10H2,1-3H3/t12-,16-,17-,20-/m0/s1
SMILESCOC(=O)C1=CO[C@@H](C)[C@@H]2CN3CCC4=C(NC5=CC(OC)=CC=C45)[C@@H]3C[C@H]12

Properties

Molecular FormulaC22H26N2O4
Molecular Weight382.46
Exact Mass382.18926
Log P (ALogP)3.19
TPSA63.79
H-Bond Donors / Acceptors1 / 5
Rotatable Bonds2
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.81
NP-likeness1.31

Classification

NP PathwayAlkaloids
NP SuperclassPseudoalkaloids
NP ClassSteroidal alkaloids
Chemical SuperclassAlkaloids and derivatives
Chemical ClassYohimbine alkaloids
Chemical SubclassYohimbine alkaloids

Reported in GR-MAPs Plants

Rauvolfia serpentina as “Rauvolfia serpentina” in COCONUT

References (20)

  1. 10.1002/JPS.2600510307
  2. 10.1002/biuz.19840140514
  3. 10.1002/food.19880321030
  4. 10.1007/BF00568358
  5. 10.1007/BF00597732
  6. 10.1007/BF00597827
  7. 10.1007/SPRINGERREFERENCE_37170
  8. 10.1016/0031-9422(72)80065-7
  9. 10.1016/0031-9422(80)85167-3
  10. 10.1016/0031-9422(91)83682-B
  11. 10.1016/0031-9422(94)00638-A
  12. 10.1016/S0031-9422(00)89757-5
  13. 10.1016/S0040-4039(01)87704-2
  14. 10.1021/NP50014A009
  15. 10.1021/NP50029A018
  16. 10.1021/NP50065A030
  17. 10.1021/np50014a009
  18. 10.1080/10575639708043638
  19. 10.1093/JAOAC/66.4.867
  20. 10.1135/CCCC19622981

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.