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COCONUT Compound
(2~{S})-2-[(1~{S})-2-[(1~{S},4~{a}~{R},5~{S},6~{R},8~{a}~{S})-6-hydroxy-5-(hydroxymethyl)-5,8~{a}-dimethyl-2-methylene-decalin-1-yl]-1-(4-oxo-3-furyl)ethyl]-4-[(~{E})-2-[(1~{S},4~{a}~{S},5~{R},6~{R},8~{a}~{S})-6-hydroxy-5-(hydroxymethyl)-5,8~{a}-dimethyl-2-methylene-decalin-1-yl]vinyl]-2~{H}-furan-5-one
CNP0426847.1 · C40H56O8 · View on COCONUT ↗
2D Structure
Identifiers
| IUPAC Name | (2~{S})-2-[(1~{S})-2-[(1~{S},4~{a}~{R},5~{S},6~{R},8~{a}~{S})-6-hydroxy-5-(hydroxymethyl)-5,8~{a}-dimethyl-2-methylene-decalin-1-yl]-1-(4-oxo-3-furyl)ethyl]-4-[(~{E})-2-[(1~{S},4~{a}~{S},5~{R},6~{R},8~{a}~{S})-6-hydroxy-5-(hydroxymethyl)-5,8~{a}-dimethyl-2-methylene-decalin-1-yl]vinyl]-2~{H}-furan-5-one |
|---|---|
| COCONUT ID | CNP0426847.1 |
| InChIKey | ZNDWLHZGUVYXSN-BWPBBXJDSA-N |
| InChI | InChI=1S/C40H56O8/c1-23-7-11-32-37(3,15-13-34(44)39(32,5)21-41)28(23)10-9-25-17-31(48-36(25)46)26(27-19-47-20-30(27)43)18-29-24(2)8-12-33-38(29,4)16-14-35(45)40(33,6)22-42/h9-10,17,19,26,28-29,31-35,41-42,44-45H,1-2,7-8,11-16,18,20-22H2,3-6H3/b10-9+/t26-,28-,29-,31-,32-,33+,34+,35+,37+,38-,39-,40+/m0/s1 |
| SMILES | C=C1CC[C@@H]2[C@](C)(CO)[C@H](O)CC[C@]2(C)[C@H]1/C=C/C1=C[C@@H]([C@@H](C[C@H]2C(=C)CC[C@H]3[C@@](C)(CO)[C@H](O)CC[C@]32C)C2=COCC2=O)OC1=O |
Properties
| Molecular Formula | C40H56O8 |
|---|---|
| Molecular Weight | 664.88 |
| Exact Mass | 664.39752 |
| Log P (ALogP) | 5.37 |
| TPSA | 133.52 |
| H-Bond Donors / Acceptors | 4 / 8 |
| Rotatable Bonds | 8 |
| Lipinski's Rule of 5 Violations | 2 |
| QED Drug-likeness | 0.20 |
| NP-likeness | 2.14 |
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 |
|---|
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.