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COCONUT Compound

5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2~{S},3~{R},4~{R},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]-8-[(2~{R},3~{S},4~{R},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]chromen-4-one

CNP0217099.9 · C26H28O14 · View on COCONUT ↗

2D Structure

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Identifiers

IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2~{S},3~{R},4~{R},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]-8-[(2~{R},3~{S},4~{R},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]chromen-4-one
COCONUT IDCNP0217099.9
InChIKeyMMDUKUSNQNWVET-OCQIDDQGSA-N
InChIInChI=1S/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)15-19(33)14-10(29)5-12(8-1-3-9(28)4-2-8)39-24(14)16(20(15)34)25-22(36)17(31)11(30)7-38-25/h1-5,11,13,17-18,21-23,25-28,30-37H,6-7H2/t11-,13-,17-,18-,21+,22+,23-,25-,26+/m1/s1
SMILESO=C1C=C(C2=CC=C(O)C=C2)OC2=C([C@H]3OC[C@@H](O)[C@@H](O)[C@@H]3O)C(O)=C([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(O)=C12

Properties

Molecular FormulaC26H28O14
Molecular Weight564.50
Exact Mass564.14791
Log P (ALogP)-1.75
TPSA250.97
H-Bond Donors / Acceptors10 / 14
Rotatable Bonds4
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.17
NP-likeness1.96

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassFlavonoids
NP ClassFlavones
Chemical SuperclassPhenylpropanoids and polyketides
Chemical ClassFlavonoids
Chemical SubclassFlavonoid glycosides

Reported in GR-MAPs Plants

Glycyrrhiza glabra as “Glycyrrhiza glabra” in COCONUT
Oryza sativa as “Oryza sativa” in COCONUT

References (9)

  1. 10.1016/0031-9422(82)83197-X
  2. 10.1016/J.PHYTOCHEM.2006.10.013
  3. 10.1016/S0031-9422(00)83183-0
  4. 10.1016/S0031-9422(01)00306-5
  5. 10.1016/S0031-9422(01)00415-0
  6. 10.1016/S0031-9422(03)00282-6
  7. 10.1016/S0031-9422(97)00956-4
  8. 10.1021/NP800691K
  9. 10.1248/CPB.51.1204

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.