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COCONUT Compound

4-[(2~{S},3~{a}~{R},5~{a}~{S},6~{R},7~{R},9~{a}~{R},9~{b}~{S})-7-hydroxy-6-(hydroxymethyl)-3~{a},6,9~{a}-trimethyl-2,4,5,5~{a},7,8,9,9~{b}-octahydro-1~{H}-benzo[e]benzofuran-2-yl]-2~{H}-furan-5-one

CNP0229241.3 · C20H30O5 · View on COCONUT ↗

2D Structure

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Identifiers

IUPAC Name4-[(2~{S},3~{a}~{R},5~{a}~{S},6~{R},7~{R},9~{a}~{R},9~{b}~{S})-7-hydroxy-6-(hydroxymethyl)-3~{a},6,9~{a}-trimethyl-2,4,5,5~{a},7,8,9,9~{b}-octahydro-1~{H}-benzo[e]benzofuran-2-yl]-2~{H}-furan-5-one
COCONUT IDCNP0229241.3
InChIKeyQTYVPMSAPQBXMM-PWSXLVATSA-N
InChIInChI=1S/C20H30O5/c1-18-7-5-16(22)19(2,11-21)14(18)4-8-20(3)15(18)10-13(25-20)12-6-9-24-17(12)23/h6,13-16,21-22H,4-5,7-11H2,1-3H3/t13-,14-,15-,16+,18+,19-,20+/m0/s1
SMILESC[C@]1(CO)[C@H]2CC[C@@]3(C)O[C@H](C4=CCOC4=O)C[C@H]3[C@]2(C)CC[C@H]1O

Properties

Molecular FormulaC20H30O5
Molecular Weight350.46
Exact Mass350.20932
Log P (ALogP)2.20
TPSA75.99
H-Bond Donors / Acceptors2 / 5
Rotatable Bonds2
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.75
NP-likeness3.32

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 (2)

  1. 10.1002/HLCA.201100236
  2. 10.1021/NP050211N

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.