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COCONUT Compound

4-[2-[(1S,2R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]ethyl]-2H-furan-5-one

CNP0367759.1 · C20H30O5 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

Name4-[2-[(1S,2R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]ethyl]-2H-furan-5-one
IUPAC Name4-[2-[(1~{S},2~{R},4~{a}~{S},5~{R},6~{R},8~{a}~{R})-6-hydroxy-5-(hydroxymethyl)-5,8~{a}-dimethyl-spiro[decalin-2,2'-oxirane]-1-yl]ethyl]-2~{H}-furan-5-one
COCONUT IDCNP0367759.1
InChIKeyYQZCSRAURNLCEK-WZLKLWACSA-N
InChIInChI=1S/C20H30O5/c1-18-8-6-16(22)19(2,11-21)14(18)5-9-20(12-25-20)15(18)4-3-13-7-10-24-17(13)23/h7,14-16,21-22H,3-6,8-12H2,1-2H3/t14-,15-,16+,18+,19-,20-/m0/s1
SMILESC[C@]1(CO)[C@H]2CC[C@]3(CO3)[C@@H](CCC3=CCOC3=O)[C@]2(C)CC[C@H]1O

Properties

Molecular FormulaC20H30O5
Molecular Weight350.46
Exact Mass350.20932
Log P (ALogP)2.20
TPSA79.29
H-Bond Donors / Acceptors2 / 5
Rotatable Bonds4
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.60
NP-likeness3.59

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. 10.1021/NP050160U
  2. 10.1021/np050160u

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.