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COCONUT Compound

Stemmadenine

CNP0203725.2 · C21H26N2O3 · View on COCONUT ↗

2D Structure

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Identifiers

NameStemmadenine
IUPAC Namemethyl (1~{R},2~{S},16~{E})-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0^{3,11}.0^{5,10}]octadeca-3(11),5,7,9-tetraene-2-carboxylate
COCONUT IDCNP0203725.2
InChIKeyMBXJCHZRHROMQA-YVDMJPQFSA-N
InChIInChI=1S/C21H26N2O3/c1-3-14-12-23-10-8-16-15-6-4-5-7-18(15)22-19(16)21(13-24,20(25)26-2)17(14)9-11-23/h3-7,17,22,24H,8-13H2,1-2H3/b14-3-/t17-,21+/m1/s1
SMILESC/C=C1/CN2CCC3=C(NC4=CC=CC=C34)[C@@](CO)(C(=O)OC)[C@@H]1CC2

Properties

Molecular FormulaC21H26N2O3
Molecular Weight354.45
Exact Mass354.19434
Log P (ALogP)2.40
TPSA65.56
H-Bond Donors / Acceptors2 / 4
Rotatable Bonds2
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.64
NP-likeness1.69

Classification

NP PathwayAlkaloids
NP SuperclassTryptophan alkaloids
NP ClassAspidosperma type
Chemical SuperclassAlkaloids and derivatives
Chemical ClassStrychnos alkaloids
Chemical SubclassStrychnos alkaloids

Reported in GR-MAPs Plants

Rauvolfia serpentina as “Rauvolfia serpentina” in COCONUT

References (9)

  1. 10.1002/MRC.1039
  2. 10.1002/PCA.567
  3. 10.1016/0031-9422(88)80456-4
  4. 10.1016/S0031-9422(00)83130-1
  5. 10.1016/S0031-9422(96)00645-0
  6. 10.1021/NP50055A036
  7. 10.1021/np50055a036
  8. 10.1055/S-2007-969804
  9. 10.1080/10575639508044076

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.