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COCONUT Compound

Vinburnine

CNP0280464.1 · C19H22N2O · View on COCONUT ↗

2D Structure

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Identifiers

NameVinburnine
IUPAC Name(15~{S},19~{S})-15-ethyl-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraen-17-one
COCONUT IDCNP0280464.1
CAS4880-88-0, 2580-88-3
InChIKeyWYJAPUKIYAZSEM-MOPGFXCFSA-N
InChIInChI=1S/C19H22N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,18H,2,5,8-12H2,1H3/t18-,19+/m1/s1
SMILESCC[C@@]12CCCN3CCC4=C([C@@H]31)N(C(=O)C2)C1=CC=CC=C41

Properties

Molecular FormulaC19H22N2O
Molecular Weight294.40
Exact Mass294.17321
Log P (ALogP)3.77
TPSA25.24
H-Bond Donors / Acceptors0 / 3
Rotatable Bonds1
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.80
NP-likeness0.89

Classification

NP PathwayAlkaloids
NP SuperclassTryptophan alkaloids
NP ClassAspidosperma type
Chemical SuperclassAlkaloids and derivatives
Chemical ClassEburnan-type alkaloids
Chemical SubclassEburnan-type alkaloids

Reported in GR-MAPs Plants

Rauvolfia serpentina as “Rauvolfia serpentina” in COCONUT

References (12)

  1. 10.1002/9780470744307.gat218
  2. 10.1002/JPS.2600620206
  3. 10.1002/PCA.2800020206
  4. 10.1002/PCA.567
  5. 10.1002/biuz.19840140514
  6. 10.1002/food.19880321030
  7. 10.1007/S10600-020-03102-2
  8. 10.1016/S0031-9422(96)00496-7
  9. 10.1021/ACS.JNATPROD.6B00011
  10. 10.1021/NP400214Y
  11. 10.1039/D2RA01791A
  12. 10.21608/BFSA.1995.69674

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.