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COCONUT Compound
chebulanin
CNP0195185.3 · C27H24O19 · View on COCONUT ↗
2D Structure
Identifiers
| Name | chebulanin |
|---|---|
| IUPAC Name | 2-[(4~{R},5~{S},7~{R},8~{S},13~{S},21~{S})-13,17,18,21-tetrahydroxy-7-(hydroxymethyl)-2,10,14-trioxo-5-(3,4,5-trihydroxybenzoyl)oxy-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 | CNP0195185.3 |
| InChIKey | HPQIRFXIDGVWBA-KEDMNDIKSA-N |
| InChI | InChI=1S/C27H24O19/c28-5-12-20-19(37)22(27(42-12)46-23(38)6-1-9(29)16(34)10(30)2-6)45-24(39)7-3-11(31)17(35)21-15(7)14(18(36)26(41)44-21)8(4-13(32)33)25(40)43-20/h1-3,8,12,14,18-20,22,27-31,34-37H,4-5H2,(H,32,33)/t8?,12-,14?,18+,19+,20-,22-,27+/m1/s1 |
| SMILES | O=C(O)CC1C(=O)O[C@H]2[C@H](O)[C@@H](OC(=O)C3=CC(O)=C(O)C4=C3C1[C@H](O)C(=O)O4)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)O[C@@H]2CO |
Properties
| Molecular Formula | C27H24O19 |
|---|---|
| Molecular Weight | 652.47 |
| Exact Mass | 652.09118 |
| Log P (ALogP) | -1.95 |
| TPSA | 313.57 |
| H-Bond Donors / Acceptors | 9 / 18 |
| Rotatable Bonds | 5 |
| Lipinski's Rule of 5 Violations | 3 |
| QED Drug-likeness | 0.07 |
| NP-likeness | 2.07 |
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 |
|---|---|
| Emblica officinalis | as “Phyllanthus emblica” 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.