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COCONUT Compound

Azadirone

CNP0244664.2 · C28H36O4 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

NameAzadirone
IUPAC Name[(5~{R},7~{R},8~{R},9~{R},10~{R},13~{S},17~{R})-17-(3-furyl)-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate
COCONUT IDCNP0244664.2
CAS25279-67-8
InChIKeyXXIKKMLIDXLAIK-RFKFVWFBSA-N
InChIInChI=1S/C28H36O4/c1-17(29)32-24-15-22-25(2,3)23(30)10-13-27(22,5)21-9-12-26(4)19(18-11-14-31-16-18)7-8-20(26)28(21,24)6/h8,10-11,13-14,16,19,21-22,24H,7,9,12,15H2,1-6H3/t19-,21+,22-,24+,26-,27+,28-/m0/s1
SMILESCC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@]3(C)C(=CC[C@H]3C3=COC=C3)[C@@]21C

Properties

Molecular FormulaC28H36O4
Molecular Weight436.59
Exact Mass436.26136
Log P (ALogP)6.24
TPSA56.51
H-Bond Donors / Acceptors0 / 4
Rotatable Bonds2
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.41
NP-likeness3.49

Classification

NP PathwayTerpenoids
NP SuperclassTriterpenoids
NP ClassLimonoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassSteroids and steroid derivatives
Chemical SubclassOxosteroids

Reported in GR-MAPs Plants

Azadirachta indica as “Azadirachta indica” in COCONUT

References (12)

  1. 10.1002/CHIN.200746148
  2. 10.1016/0031-9422(90)87113-9
  3. 10.1016/S0031-9422(00)90423-0
  4. 10.1016/S0031-9422(97)00378-6
  5. 10.1016/j.jep.2015.08.039
  6. 10.1021/NP100325Q
  7. 10.1021/NP50079A012
  8. 10.1021/NP50081A005
  9. 10.1039/P19750001758
  10. 10.1248/CPB.55.1442
  11. 10.1515/ZNB-1986-0720
  12. 10.3987/REV-98-SR(H)5

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.