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COCONUT Compound
(3E,4S)-3-{2-[(2aR,4aS,5R,8aS,8bR)-4a,8b-dimethyl-6-methylidene-decahydro-1H-naphtho[2,1-b]oxet-5-yl]ethylidene}-4-hydroxyoxolan-2-one
CNP0300061.1 · C20H28O4 · View on COCONUT ↗
2D Structure
Identifiers
| Name | (3E,4S)-3-{2-[(2aR,4aS,5R,8aS,8bR)-4a,8b-dimethyl-6-methylidene-decahydro-1H-naphtho[2,1-b]oxet-5-yl]ethylidene}-4-hydroxyoxolan-2-one |
|---|---|
| IUPAC Name | (3~{E},4~{S})-3-[2-[(2~{a}~{R},4~{a}~{S},5~{R},8~{a}~{S},8~{b}~{R})-4~{a},8~{b}-dimethyl-6-methylene-1,2~{a},3,4,5,7,8,8~{a}-octahydronaphtho[2,1-b]oxet-5-yl]ethylidene]-4-hydroxy-tetrahydrofuran-2-one |
| COCONUT ID | CNP0300061.1 |
| InChIKey | NSMZHQPCABSPEV-OTESTREVSA-N |
| InChI | InChI=1S/C20H28O4/c1-12-4-7-16-19(2,9-8-17-20(16,3)11-24-17)14(12)6-5-13-15(21)10-23-18(13)22/h5,14-17,21H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1 |
| SMILES | C=C1CC[C@@H]2[C@]3(C)CO[C@@H]3CC[C@@]2(C)[C@@H]1C/C=C1/C(=O)OC[C@H]1O |
Properties
| Molecular Formula | C20H28O4 |
|---|---|
| Molecular Weight | 332.44 |
| Exact Mass | 332.19876 |
| Log P (ALogP) | 3.01 |
| TPSA | 55.76 |
| H-Bond Donors / Acceptors | 1 / 4 |
| Rotatable Bonds | 2 |
| Lipinski's Rule of 5 Violations | 0 |
| QED Drug-likeness | 0.48 |
| NP-likeness | 3.54 |
Classification
| NP Pathway | Terpenoids |
|---|---|
| NP Superclass | Diterpenoids |
| NP Class | Labdane diterpenoids |
| Chemical Superclass | Organoheterocyclic compounds |
| Chemical Class | Lactones |
| Chemical Subclass | Gamma butyrolactones |
Reported in GR-MAPs Plants
| Andrographis paniculata | as “Andrographis paniculata” in COCONUT |
|---|
References (1)
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.