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COCONUT Compound

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-4H-chromen-4-one

CNP0388516.5 · C20H18O11 · View on COCONUT ↗

2D Structure

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Identifiers

Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-4H-chromen-4-one
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2~{R},3~{R},4~{S},5~{S})-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-chromen-4-one
COCONUT IDCNP0388516.5
InChIKeyPZZRDJXEMZMZFD-JNEVDQRJSA-N
InChIInChI=1S/C20H18O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17,20-26,28H,6H2/t12-,15-,17+,20+/m0/s1
SMILESO=C1C(O[C@H]2OC[C@H](O)[C@H](O)[C@H]2O)=C(C2=CC=C(O)C(O)=C2)OC2=CC(O)=CC(O)=C12

Properties

Molecular FormulaC20H18O11
Molecular Weight434.35
Exact Mass434.08491
Log P (ALogP)0.10
TPSA190.28
H-Bond Donors / Acceptors7 / 11
Rotatable Bonds3
Lipinski's Rule of 5 Violations2
QED Drug-likeness0.28
NP-likeness2.04

Classification

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

Reported in GR-MAPs Plants

Foeniculum vulgare as “Foeniculum vulgare” in COCONUT

References (15)

  1. 10.1002/ARDP.2503240811
  2. 10.1002/JCCS.199900034
  3. 10.1007/BF00577214
  4. 10.1007/BF00598324
  5. 10.1007/BF00598597
  6. 10.1016/0031-9422(88)80645-9
  7. 10.1016/J.PHYTOCHEM.2006.03.004
  8. 10.1016/S0031-9422(00)83511-6
  9. 10.1016/S0031-9422(00)91077-X
  10. 10.1016/S0031-9422(97)00370-1
  11. 10.1016/S0367-326X(00)00252-5
  12. 10.1016/s0367-326x(00)00252-5
  13. 10.1021/NP040024+
  14. 10.1021/NP200646E
  15. 10.1055/S-2002-20053

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.