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COCONUT Compound

(1~{S},2~{R},3~{S},5~{R},6~{S},8~{R},9~{S},10~{S},13~{S},16~{R},17~{R},18~{S})-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-one

CNP0191058.3 · C25H39NO7 · View on COCONUT ↗

2D Structure

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Identifiers

IUPAC Name(1~{S},2~{R},3~{S},5~{R},6~{S},8~{R},9~{S},10~{S},13~{S},16~{R},17~{R},18~{S})-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-one
COCONUT IDCNP0191058.3
InChIKeyMWOQLGAENOKSHS-HNUYGTDJSA-N
InChIInChI=1S/C25H39NO7/c1-6-26-11-22(12-30-2)8-7-16(32-4)24-14-9-13-15(31-3)10-23(28,17(14)18(13)27)25(29,21(24)26)20(33-5)19(22)24/h13-17,19-21,28-29H,6-12H2,1-5H3/t13-,14-,15+,16-,17-,19-,20+,21+,22+,23-,24+,25-/m1/s1
SMILESCCN1C[C@]2(COC)CC[C@@H](OC)[C@@]34[C@@H]5C[C@H]6C(=O)[C@@H]5[C@](O)(C[C@@H]6OC)[C@@](O)([C@@H](OC)[C@H]23)[C@@H]14

Properties

Molecular FormulaC25H39NO7
Molecular Weight465.59
Exact Mass465.27265
Log P (ALogP)0.48
TPSA97.69
H-Bond Donors / Acceptors2 / 8
Rotatable Bonds6
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.58
NP-likeness3.38

Classification

NP PathwayAlkaloids
NP SuperclassPseudoalkaloids
NP ClassTerpenoid alkaloids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassDiterpenoids

Reported in GR-MAPs Plants

Mucuna pruriens as “Mucuna pruriens” in COCONUT

References (3)

  1. 10.1007/BF00565884
  2. 10.1021/NP800439A
  3. 10.1139/V66-001

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.