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COCONUT Compound

Alstonine

CNP0593697.1 · C21H20N2O3 · View on COCONUT ↗

2D Structure

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Identifiers

NameAlstonine
IUPAC Namemethyl (15~{S},16~{S},20~{S})-16-methyl-17-oxa-13-azonia-3-azanidapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1,4,6,8,10,12,18-heptaene-19-carboxylate
COCONUT IDCNP0593697.1
InChIKeyWYTGDNHDOZPMIW-RCBQFDQVSA-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]2C[N+]3=CC=C4C(=C3C[C@H]12)[N-]C1=CC=CC=C14

Properties

Molecular FormulaC21H20N2O3
Molecular Weight348.40
Exact Mass348.14739
Log P (ALogP)2.50
TPSA53.51
H-Bond Donors / Acceptors0 / 3
Rotatable Bonds1
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.50
NP-likeness1.41

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
Rauvolfia serpentina as “Rauvolfia serpentina” in COCONUT

References (13)

  1. 10.1002/JPS.3030460815
  2. 10.1007/BF00267656
  3. 10.1007/BF00607562
  4. 10.1007/S11101-006-9047-8
  5. 10.1016/0378-8741(81)90022-2
  6. 10.1016/S0021-9673(00)90403-5
  7. 10.1016/S0099-9598(08)60080-2
  8. 10.1021/JO01200A015
  9. 10.1039/JR9340000287
  10. 10.1055/S-2007-969925
  11. 10.1071/CH9702489
  12. 10.2174/0929867043455846
  13. 10.3987/R-1981-10-1727

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.