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COCONUT Compound

Ajugalactone

CNP0382209.2 · C29H40O8 · View on COCONUT ↗

2D Structure

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Identifiers

NameAjugalactone
IUPAC Name(2~{S},3~{R},5~{R},9~{R},10~{R},13~{R},14~{R},17~{S})-17-[(1~{R})-1-[(2~{R})-4-ethyl-5-methyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxy-ethyl]-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,11,15,16,17-decahydrocyclopenta[a]phenanthrene-6,12-dione
COCONUT IDCNP0382209.2
CAS42975-12-2
InChIKeyLLPOMLNTBDOEOC-LYUHEGIFSA-N
InChIInChI=1S/C29H40O8/c1-6-15-9-24(37-25(34)14(15)2)28(5,35)22-7-8-29(36)17-10-19(30)18-11-20(31)21(32)13-26(18,3)16(17)12-23(33)27(22,29)4/h10,16,18,20-22,24,31-32,35-36H,6-9,11-13H2,1-5H3/t16-,18-,20+,21-,22-,24+,26+,27-,28+,29+/m0/s1
SMILESCCC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@H]2CC[C@@]3(O)C4=CC(=O)[C@@H]5C[C@@H](O)[C@@H](O)C[C@]5(C)[C@H]4CC(=O)[C@]23C)C1

Properties

Molecular FormulaC29H40O8
Molecular Weight516.63
Exact Mass516.27232
Log P (ALogP)2.16
TPSA141.36
H-Bond Donors / Acceptors4 / 8
Rotatable Bonds3
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.42
NP-likeness3.51

Classification

NP PathwayTerpenoids
NP SuperclassSteroids
NP ClassEcdysteroids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassSteroids and steroid derivatives
Chemical SubclassSteroid lactones

Reported in GR-MAPs Plants

Ajuga chamaepitys as “Ajuga chamaepitys” in COCONUT

References (15)

  1. 10.1002/CHIN.200550175
  2. 10.1007/BF00573570
  3. 10.1007/BF00574363
  4. 10.1007/BF01134622
  5. 10.1016/0031-9422(92)83112-C
  6. 10.1016/0040-4020(95)00767-3
  7. 10.1016/0040-4020(96)00536-4
  8. 10.1016/S0021-9673(01)88168-1
  9. 10.1016/S0021-9673(01)89391-2
  10. 10.1016/S0031-9422(00)84101-1
  11. 10.1016/S0031-9422(00)94988-4
  12. 10.1016/S0031-9422(00)97527-7
  13. 10.1246/CL.1982.1313
  14. 10.1248/CPB.53.836
  15. 10.1248/CPB.59.1065

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.