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COCONUT Compound
[(1~{R},2~{S},3~{R},4~{a}~{R},5~{S},6~{R},8~{S},8~{a}~{R})-5-[(3~{a}~{S},5~{S},6~{a}~{S})-3~{a},4,5,6~{a}-tetrahydrofuro[2,3-b]furan-5-yl]-8-acetoxy-8~{a}-(acetoxymethyl)-3-hydroxy-5,6-dimethyl-spiro[decalin-1,2'-oxirane]-2-yl] (2~{R},3~{S})-3-acetoxy-2-methyl-butanoate
CNP0210520.2 · C31H44O12 · View on COCONUT ↗
2D Structure
Identifiers
| IUPAC Name | [(1~{R},2~{S},3~{R},4~{a}~{R},5~{S},6~{R},8~{S},8~{a}~{R})-5-[(3~{a}~{S},5~{S},6~{a}~{S})-3~{a},4,5,6~{a}-tetrahydrofuro[2,3-b]furan-5-yl]-8-acetoxy-8~{a}-(acetoxymethyl)-3-hydroxy-5,6-dimethyl-spiro[decalin-1,2'-oxirane]-2-yl] (2~{R},3~{S})-3-acetoxy-2-methyl-butanoate |
|---|---|
| COCONUT ID | CNP0210520.2 |
| InChIKey | SVYZIDAZJUAUJN-WZCVCQNVSA-N |
| InChI | InChI=1S/C31H44O12/c1-15-10-25(41-20(6)34)30(13-38-18(4)32)23(29(15,7)24-11-21-8-9-37-28(21)42-24)12-22(35)26(31(30)14-39-31)43-27(36)16(2)17(3)40-19(5)33/h8-9,15-17,21-26,28,35H,10-14H2,1-7H3/t15-,16-,17+,21-,22-,23-,24+,25+,26+,28+,29+,30+,31-/m1/s1 |
| SMILES | CC(=O)OC[C@@]12[C@@H](OC(C)=O)C[C@@H](C)[C@](C)([C@@H]3C[C@H]4C=CO[C@H]4O3)[C@H]1C[C@@H](O)[C@H](OC(=O)[C@H](C)[C@H](C)OC(C)=O)[C@]21CO1 |
Properties
| Molecular Formula | C31H44O12 |
|---|---|
| Molecular Weight | 608.68 |
| Exact Mass | 608.28328 |
| Log P (ALogP) | 2.44 |
| TPSA | 156.42 |
| H-Bond Donors / Acceptors | 1 / 12 |
| Rotatable Bonds | 8 |
| Lipinski's Rule of 5 Violations | 2 |
| QED Drug-likeness | 0.24 |
| NP-likeness | 3.23 |
Classification
| NP Pathway | Terpenoids |
|---|---|
| NP Superclass | Diterpenoids |
| NP Class | Colensane and Clerodane diterpenoids |
| Chemical Superclass | Organic acids and derivatives |
| Chemical Class | Carboxylic acids and derivatives |
| Chemical Subclass | Tetracarboxylic acids and derivatives |
Reported in GR-MAPs Plants
| Ajuga chamaepitys | as “Ajuga chamaepitys” 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.