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COCONUT Compound

14-Deoxy-11-oxoandrographolide

CNP0295287.2 · C20H28O5 · View on COCONUT ↗

2D Structure

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Identifiers

Name14-Deoxy-11-oxoandrographolide
IUPAC Name4-[2-[(1~{R},4~{a}~{S},5~{R},6~{R},8~{a}~{R})-6-hydroxy-5-(hydroxymethyl)-5,8~{a}-dimethyl-2-methylene-decalin-1-yl]-2-oxo-ethyl]-2~{H}-furan-5-one
COCONUT IDCNP0295287.2
CAS42895-57-8
InChIKeyWZHWNAKOQGIEEB-NDLGOLERSA-N
InChIInChI=1S/C20H28O5/c1-12-4-5-15-19(2,8-6-16(23)20(15,3)11-21)17(12)14(22)10-13-7-9-25-18(13)24/h7,15-17,21,23H,1,4-6,8-11H2,2-3H3/t15-,16+,17-,19+,20-/m0/s1
SMILESC=C1CC[C@H]2[C@@](C)(CC[C@@H](O)[C@@]2(C)CO)[C@@H]1C(=O)CC1=CCOC1=O

Properties

Molecular FormulaC20H28O5
Molecular Weight348.44
Exact Mass348.19367
Log P (ALogP)2.17
TPSA83.83
H-Bond Donors / Acceptors2 / 5
Rotatable Bonds4
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.60
NP-likeness3.02

Classification

NP PathwayTerpenoids
NP SuperclassDiterpenoids
NP ClassLabdane diterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassTerpene lactones

Reported in GR-MAPs Plants

Andrographis paniculata as “Andrographis paniculata” in COCONUT

References (4)

  1. 10.1002/CHIN.201029197
  2. 10.1021/NP050160U
  3. 10.1039/P19730001247
  4. 10.3390/MOLECULES191118332

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.