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COCONUT Compound
orthosiphol R
CNP0162117.1 · C38H44O12 · View on COCONUT ↗
2D Structure
Identifiers
| Name | orthosiphol R |
|---|---|
| IUPAC Name | [(2~{S},3~{S},4~{S},4~{a}~{S},4~{b}~{S},5~{R},6~{S},7~{S},8~{a}~{S},10~{R},10~{a}~{R})-7,10-diacetoxy-5-benzoyloxy-3,6,10~{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 | CNP0162117.1 |
| InChIKey | UVLMOXBOUWFDIG-PQEFSWHNSA-N |
| InChI | InChI=1S/C38H44O12/c1-8-36(6)29(42)27(49-32(43)22-15-11-9-12-16-22)28-37(7)24(19-25(47-20(2)39)38(28,46)34(36)45)35(4,5)30(48-21(3)40)26(41)31(37)50-33(44)23-17-13-10-14-18-23/h8-18,24-31,41-42,46H,1,19H2,2-7H3/t24-,25+,26-,27-,28+,29+,30+,31-,36-,37-,38-/m0/s1 |
| SMILES | C=C[C@]1(C)C(=O)[C@]2(O)[C@H](OC(C)=O)C[C@H]3C(C)(C)[C@H](OC(C)=O)[C@H](O)[C@H](OC(=O)C4=CC=CC=C4)[C@]3(C)[C@H]2[C@H](OC(=O)C2=CC=CC=C2)[C@H]1O |
Properties
| Molecular Formula | C38H44O12 |
|---|---|
| Molecular Weight | 692.76 |
| Exact Mass | 692.28328 |
| Log P (ALogP) | 3.21 |
| TPSA | 182.96 |
| H-Bond Donors / Acceptors | 3 / 12 |
| Rotatable Bonds | 7 |
| Lipinski's Rule of 5 Violations | 2 |
| QED Drug-likeness | 0.22 |
| NP-likeness | 2.14 |
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 |
|---|
References (2)
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.