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COCONUT Compound
[(1~{S},3~{R},5~{R},6~{a}~{S},7~{R},8~{R},10~{S},10~{a}~{S})-1,3-diacetoxy-10-hydroxy-7,8-dimethyl-7-[(2~{E})-3-methylpenta-2,4-dienyl]-1,3,5,6,6~{a},8,9,10-octahydrobenzo[d]isobenzofuran-5-yl] 2-methylpropanoate
CNP0165942.4 · C28H40O8 · View on COCONUT ↗
2D Structure
Identifiers
| IUPAC Name | [(1~{S},3~{R},5~{R},6~{a}~{S},7~{R},8~{R},10~{S},10~{a}~{S})-1,3-diacetoxy-10-hydroxy-7,8-dimethyl-7-[(2~{E})-3-methylpenta-2,4-dienyl]-1,3,5,6,6~{a},8,9,10-octahydrobenzo[d]isobenzofuran-5-yl] 2-methylpropanoate |
|---|---|
| COCONUT ID | CNP0165942.4 |
| InChIKey | PASSAFHUDJPXAL-BTPFWLCYSA-N |
| InChI | InChI=1S/C28H40O8/c1-9-16(4)10-11-27(8)17(5)12-23(31)28-21(13-20(14-22(27)28)35-24(32)15(2)3)25(33-18(6)29)36-26(28)34-19(7)30/h9-10,13,15,17,20,22-23,25-26,31H,1,11-12,14H2,2-8H3/b16-10+/t17-,20+,22+,23+,25+,26-,27-,28-/m1/s1 |
| SMILES | C=C/C(C)=C/C[C@]1(C)[C@H](C)C[C@H](O)[C@@]23C(=C[C@H](OC(=O)C(C)C)C[C@@H]12)[C@@H](OC(C)=O)O[C@H]3OC(C)=O |
Properties
| Molecular Formula | C28H40O8 |
|---|---|
| Molecular Weight | 504.62 |
| Exact Mass | 504.27232 |
| Log P (ALogP) | 4.22 |
| TPSA | 108.36 |
| H-Bond Donors / Acceptors | 1 / 8 |
| Rotatable Bonds | 7 |
| Lipinski's Rule of 5 Violations | 1 |
| QED Drug-likeness | 0.24 |
| NP-likeness | 3.52 |
Classification
| NP Pathway | Terpenoids |
|---|---|
| NP Superclass | Diterpenoids |
| NP Class | Colensane and Clerodane diterpenoids |
| Chemical Superclass | Lipids and lipid-like molecules |
| Chemical Class | Prenol lipids |
| Chemical Subclass | Diterpenoids |
Reported in GR-MAPs Plants
| Cymbopogon flexuosus | as “Cymbopogon flexuosus” 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.