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COCONUT Compound
Chebulinic acid
CNP0157329.5 · C41H32O27 · View on COCONUT ↗
2D Structure
Identifiers
| Name | Chebulinic acid |
|---|---|
| IUPAC Name | 2-[(5~{S},7~{R},11~{S},12~{S},13~{S},21~{S})-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis[(3,4,5-trihydroxybenzoyl)oxy]-7-[(3,4,5-trihydroxybenzoyl)oxymethyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1^{4,8}.0^{16,20}]henicosa-1(19),16(20),17-trien-11-yl]acetic acid |
| COCONUT ID | CNP0157329.5 |
| InChIKey | YGVHOSGNOYKRIH-NJMLMDEQSA-N |
| InChI | InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22+,24-,30-,31?,33-,34?,41-/m0/s1 |
| SMILES | O=C(O)C[C@@H]1C(=O)OC2[C@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)C(OC(=O)C3=CC(O)=C(O)C4=C3[C@H]1[C@H](O)C(=O)O4)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)O[C@@H]2COC(=O)C1=CC(O)=C(O)C(O)=C1 |
Properties
| Molecular Formula | C41H32O27 |
|---|---|
| Molecular Weight | 956.68 |
| Exact Mass | 956.11310 |
| Log P (ALogP) | 0.02 |
| TPSA | 447.09 |
| H-Bond Donors / Acceptors | 13 / 26 |
| Rotatable Bonds | 9 |
| Lipinski's Rule of 5 Violations | 3 |
| QED Drug-likeness | 0.05 |
| NP-likeness | 1.30 |
Classification
| NP Pathway | Shikimates and Phenylpropanoids |
|---|---|
| NP Superclass | Phenolic acids (C6-C1) |
| NP Class | Gallotannins |
| Chemical Superclass | Phenylpropanoids and polyketides |
| Chemical Class | Tannins |
| Chemical Subclass | Hydrolyzable tannins |
Reported in GR-MAPs Plants
| Terminalia chebula | as “Terminalia chebula” in COCONUT |
|---|---|
| Terminalia bellirica | as “Terminalia bellirica” in COCONUT |
| Emblica officinalis | as “Phyllanthus emblica” 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.