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COCONUT Compound
[(2~{R},4~{R},4~{a}~{R},4~{b}~{S},5~{R},6~{S},7~{S},8~{a}~{S},10~{R},10~{a}~{R})-10-acetoxy-5-benzoyloxy-6,7,10~{a}-trihydroxy-2,4~{b},8,8-tetramethyl-1-oxo-2-vinyl-4,4~{a},5,6,7,8~{a},9,10-octahydro-3~{H}-phenanthren-4-yl] benzoate
CNP0288187.2 · C36H42O10 · View on COCONUT ↗
2D Structure
Identifiers
| Name | [(2~{R},4~{R},4~{a}~{R},4~{b}~{S},5~{R},6~{S},7~{S},8~{a}~{S},10~{R},10~{a}~{R})-10-acetoxy-5-benzoyloxy-6,7,10~{a}-trihydroxy-2,4~{b},8,8-tetramethyl-1-oxo-2-vinyl-4,4~{a},5,6,7,8~{a},9,10-octahydro-3~{H}-phenanthren-4-yl] benzoate |
|---|---|
| IUPAC Name | [(2~{R},4~{R},4~{a}~{R},4~{b}~{S},5~{R},6~{S},7~{S},8~{a}~{S},10~{R},10~{a}~{R})-10-acetoxy-5-benzoyloxy-6,7,10~{a}-trihydroxy-2,4~{b},8,8-tetramethyl-1-oxo-2-vinyl-4,4~{a},5,6,7,8~{a},9,10-octahydro-3~{H}-phenanthren-4-yl] benzoate |
| COCONUT ID | CNP0288187.2 |
| InChIKey | XZOHHNDEJRVJSL-RVGVOMRMSA-N |
| InChI | InChI=1S/C36H42O10/c1-7-34(5)19-23(45-30(40)21-14-10-8-11-15-21)27-35(6)24(18-25(44-20(2)37)36(27,43)32(34)42)33(3,4)28(39)26(38)29(35)46-31(41)22-16-12-9-13-17-22/h7-17,23-29,38-39,43H,1,18-19H2,2-6H3/t23-,24+,25-,26+,27+,28-,29+,34+,35+,36+/m1/s1 |
| SMILES | C=C[C@@]1(C)C[C@@H](OC(=O)C2=CC=CC=C2)[C@@H]2[C@](O)(C1=O)[C@H](OC(C)=O)C[C@H]1C(C)(C)[C@H](O)[C@H](O)[C@H](OC(=O)C3=CC=CC=C3)[C@]21C |
Properties
| Molecular Formula | C36H42O10 |
|---|---|
| Molecular Weight | 634.72 |
| Exact Mass | 634.27780 |
| Log P (ALogP) | 3.67 |
| TPSA | 156.66 |
| H-Bond Donors / Acceptors | 3 / 10 |
| Rotatable Bonds | 6 |
| Lipinski's Rule of 5 Violations | 1 |
| QED Drug-likeness | 0.24 |
| NP-likeness | 2.30 |
Classification
| NP Pathway | Terpenoids |
|---|---|
| NP Superclass | Diterpenoids |
| NP Class | Pimarane and Isopimarane diterpenoids |
| Chemical Superclass | Lipids and lipid-like molecules |
| Chemical Class | Prenol lipids |
| Chemical Subclass | Diterpenoids |
Reported in GR-MAPs Plants
| Oryza sativa | as “Oryza sativa” 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.