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COCONUT Compound
(2~{S},3~{S},4~{S},5~{R},6~{R})-6-[(3~{R},4~{S},5~{R},6~{S})-6-[(2~{R},3~{R},4~{S},5~{R},6~{R})-2-[[(2~{R},3~{R},4~{S},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{R},8~{a}~{R},11~{S},12~{a}~{S},14~{a}~{R},14~{b}~{R})-8~{a}-carboxy-2,8-dihydroxy-4,11-bis(hydroxymethyl)-4,6~{a},6~{b},11,14~{b}-pentamethyl-1,2,3,4~{a},5,6,7,8,9,10,12,12~{a},14,14~{a}-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]oxy-4-hydroxy-5-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
CNP0253152.1 · C53H84O27 · View on COCONUT ↗
2D Structure
Identifiers
| IUPAC Name | (2~{S},3~{S},4~{S},5~{R},6~{R})-6-[(3~{R},4~{S},5~{R},6~{S})-6-[(2~{R},3~{R},4~{S},5~{R},6~{R})-2-[[(2~{R},3~{R},4~{S},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{R},8~{a}~{R},11~{S},12~{a}~{S},14~{a}~{R},14~{b}~{R})-8~{a}-carboxy-2,8-dihydroxy-4,11-bis(hydroxymethyl)-4,6~{a},6~{b},11,14~{b}-pentamethyl-1,2,3,4~{a},5,6,7,8,9,10,12,12~{a},14,14~{a}-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]oxy-4-hydroxy-5-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid |
|---|---|
| COCONUT ID | CNP0253152.1 |
| InChIKey | QLVCEQYJOLNGAT-HTBNDGEZSA-N |
| InChI | InChI=1S/C53H84O27/c1-48(18-56)10-11-53(47(71)72)21(12-48)20-6-7-27-49(2)13-22(58)41(50(3,19-57)26(49)8-9-51(27,4)52(20,5)14-28(53)59)80-45-37(68)38(30(61)24(16-55)75-45)77-46-40(79-43-35(66)32(63)29(60)23(15-54)74-43)31(62)25(17-73-46)76-44-36(67)33(64)34(65)39(78-44)42(69)70/h6,21-41,43-46,54-68H,7-19H2,1-5H3,(H,69,70)(H,71,72)/t21-,22+,23+,24+,25+,26+,27+,28+,29+,30+,31-,32-,33-,34-,35+,36+,37+,38-,39-,40+,41-,43-,44+,45-,46-,48-,49-,50+,51+,52+,53+/m0/s1 |
| SMILES | C[C@]1(CO)CC[C@]2(C(=O)O)[C@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@@H]7OC[C@@H](O[C@@H]8O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)[C@](C)(CO)[C@@H]5CC[C@]43C)[C@@H]2C1 |
Properties
| Molecular Formula | C53H84O27 |
|---|---|
| Molecular Weight | 1153.23 |
| Exact Mass | 1152.52000 |
| Log P (ALogP) | -4.85 |
| TPSA | 451.89 |
| H-Bond Donors / Acceptors | 17 / 25 |
| Rotatable Bonds | 14 |
| Lipinski's Rule of 5 Violations | 3 |
| QED Drug-likeness | 0.06 |
| NP-likeness | 2.26 |
Classification
| NP Pathway | Terpenoids |
|---|---|
| NP Superclass | Triterpenoids |
| NP Class | Oleanane triterpenoids |
| Chemical Superclass | Lipids and lipid-like molecules |
| Chemical Class | Steroids and steroid derivatives |
| Chemical Subclass | Hydroxysteroids |
Reported in GR-MAPs Plants
| Cassia angustifolia | as “Senna alexandrina” 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.