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COCONUT Compound

Serpentine (alkaloid)

CNP0180904.3 · C21H20N2O3 · View on COCONUT ↗

2D Structure

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Identifiers

NameSerpentine (alkaloid)
IUPAC Namemethyl (15~{R},16~{S},20~{S})-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1,3,5,7,9,11,18-heptaene-19-carboxylate
COCONUT IDCNP0180904.3
CAS131-07-7
InChIKeyWYTGDNHDOZPMIW-VBNZEHGJSA-N
InChIInChI=1S/C21H20N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-8,11-12,15-16H,9-10H2,1-2H3/t12-,15-,16+/m0/s1
SMILESCOC(=O)C1=CO[C@@H](C)[C@H]2CN3C=CC4=C5C=CC=CC5=NC4=C3C[C@H]12

Properties

Molecular FormulaC21H20N2O3
Molecular Weight348.40
Exact Mass348.14739
Log P (ALogP)3.41
TPSA53.35
H-Bond Donors / Acceptors0 / 5
Rotatable Bonds1
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.63
NP-likeness1.12

Classification

NP PathwayAlkaloids
NP SuperclassTryptophan alkaloids
NP ClassCorynanthe type
Chemical SuperclassOrganoheterocyclic compounds
Chemical ClassIndoles and derivatives
Chemical SubclassPyridoindoles

Reported in GR-MAPs Plants

Catharanthus roseus as “Catharanthus roseus” in COCONUT
Mucuna pruriens as “Mucuna pruriens” in COCONUT
Rauvolfia serpentina as “Rauvolfia serpentina” in COCONUT
Solanum lycopersicum as “Solanum lycopersicum” in COCONUT

References (38)

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  10. 10.1007/BF00267656
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  12. 10.1007/BF00607562
  13. 10.1007/BF00629934
  14. 10.1007/S11627-001-0013-2
  15. 10.1016/0141-0229(88)90045-2
  16. 10.1016/0168-1656(91)90260-3
  17. 10.1016/0378-8741(84)90046-1
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  20. 10.1016/S0031-9422(00)94768-X
  21. 10.1016/S0031-9422(02)00372-2
  22. 10.1016/S0031-9422(97)00302-6
  23. 10.1016/S0099-9598(08)60080-2
  24. 10.1016/S0141-0229(01)00309-X
  25. 10.1055/S-0028-1097468
  26. 10.1055/S-2006-959439
  27. 10.1055/S-2006-962741
  28. 10.1055/S-2007-969097
  29. 10.1055/S-2007-969782
  30. 10.1055/S-2007-969971
  31. 10.1055/S-2007-971482
  32. 10.1080/10575639708043638
  33. 10.1093/CHROMSCI/28.4.173
  34. 10.1093/JAOAC/66.4.867
  35. 10.1248/CPB.7.713
  36. 10.2174/0929867043455846
  37. 10.5586/ASBP.2001.033
  38. 10.7124/BC.000291

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.