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COCONUT Compound
4-[(~{E})-2-[(1~{S},3~{R},4~{a}~{S},5~{R},6~{R},8~{a}~{R})-3,6-dihydroxy-5-(hydroxymethyl)-5,8~{a}-dimethyl-2-methylene-decalin-1-yl]vinyl]-2~{H}-furan-5-one
CNP0396334.1 · C20H28O5 · View on COCONUT ↗
2D Structure
Identifiers
| IUPAC Name | 4-[(~{E})-2-[(1~{S},3~{R},4~{a}~{S},5~{R},6~{R},8~{a}~{R})-3,6-dihydroxy-5-(hydroxymethyl)-5,8~{a}-dimethyl-2-methylene-decalin-1-yl]vinyl]-2~{H}-furan-5-one |
|---|---|
| COCONUT ID | CNP0396334.1 |
| InChIKey | GVULAPZJWRQNHX-KSWNFVJPSA-N |
| InChI | InChI=1S/C20H28O5/c1-12-14(5-4-13-7-9-25-18(13)24)19(2)8-6-17(23)20(3,11-21)16(19)10-15(12)22/h4-5,7,14-17,21-23H,1,6,8-11H2,2-3H3/b5-4+/t14-,15-,16+,17-,19+,20+/m1/s1 |
| SMILES | C=C1[C@H](O)C[C@@H]2[C@](C)(CO)[C@H](O)CC[C@@]2(C)[C@@H]1/C=C/C1=CCOC1=O |
Properties
| Molecular Formula | C20H28O5 |
|---|---|
| Molecular Weight | 348.44 |
| Exact Mass | 348.19367 |
| Log P (ALogP) | 1.74 |
| TPSA | 86.99 |
| H-Bond Donors / Acceptors | 3 / 5 |
| Rotatable Bonds | 3 |
| Lipinski's Rule of 5 Violations | 0 |
| QED Drug-likeness | 0.53 |
| NP-likeness | 3.71 |
Classification
| NP Pathway | Terpenoids |
|---|---|
| NP Superclass | Diterpenoids |
| NP Class | Labdane diterpenoids |
| Chemical Superclass | Lipids and lipid-like molecules |
| Chemical Class | Prenol lipids |
| Chemical Subclass | Terpene lactones |
Reported in GR-MAPs Plants
| Andrographis paniculata | as “Andrographis paniculata” in COCONUT |
|---|
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.