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COCONUT Compound
9-[2-carboxy-5-[(2~{S},3~{R},4~{S},5~{R},6~{R})-4,5-dihydroxy-6-(hydroxymethyl)-3-oxalooxy-tetrahydropyran-2-yl]oxy-4-hydroxy-10-oxo-9~{H}-anthracen-9-yl]-4-hydroxy-10-oxo-5-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-9~{H}-anthracene-2-carboxylic acid
CNP0076205.1 · C44H38O23 · View on COCONUT ↗
2D Structure
Identifiers
| IUPAC Name | 9-[2-carboxy-5-[(2~{S},3~{R},4~{S},5~{R},6~{R})-4,5-dihydroxy-6-(hydroxymethyl)-3-oxalooxy-tetrahydropyran-2-yl]oxy-4-hydroxy-10-oxo-9~{H}-anthracen-9-yl]-4-hydroxy-10-oxo-5-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-9~{H}-anthracene-2-carboxylic acid |
|---|---|
| COCONUT ID | CNP0076205.1 |
| InChIKey | WCXZMEMQOKTKSI-GCIQHGODSA-N |
| InChI | InChI=1S/C44H38O23/c45-11-23-31(49)35(53)37(55)43(65-23)63-21-5-1-3-15-25(17-7-13(39(56)57)9-19(47)27(17)33(51)29(15)21)26-16-4-2-6-22(30(16)34(52)28-18(26)8-14(40(58)59)10-20(28)48)64-44-38(67-42(62)41(60)61)36(54)32(50)24(12-46)66-44/h1-10,23-26,31-32,35-38,43-50,53-55H,11-12H2,(H,56,57)(H,58,59)(H,60,61)/t23-,24-,25?,26?,31+,32+,35+,36+,37-,38-,43-,44-/m1/s1 |
| SMILES | O=C(O)C(=O)O[C@H]1[C@H](OC2=CC=CC3=C2C(=O)C2=C(O)C=C(C(=O)O)C=C2C3C2C3=CC(C(=O)O)=CC(O)=C3C(=O)C3=C(O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)C=CC=C32)O[C@H](CO)[C@H](O)[C@@H]1O |
Properties
| Molecular Formula | C44H38O23 |
|---|---|
| Molecular Weight | 934.77 |
| Exact Mass | 934.18039 |
| Log P (ALogP) | -1.46 |
| TPSA | 391.33 |
| H-Bond Donors / Acceptors | 12 / 20 |
| Rotatable Bonds | 10 |
| Lipinski's Rule of 5 Violations | 3 |
| QED Drug-likeness | 0.06 |
| NP-likeness | 1.22 |
Classification
| NP Pathway | Polyketides |
|---|---|
| NP Superclass | Polycyclic aromatic polyketides |
| NP Class | Anthraquinones and anthrones |
| Chemical Superclass | Benzenoids |
| Chemical Class | Anthracenes |
| Chemical Subclass | Anthracenecarboxylic acids and derivatives |
Reported in GR-MAPs Plants
| Cassia angustifolia | as “Senna alexandrina” 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.