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COCONUT Compound

5-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one

CNP0182333.1 · C27H30O15 · View on COCONUT ↗

2D Structure

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Identifiers

Name5-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
IUPAC Name5-hydroxy-2-(4-hydroxyphenyl)-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-7-[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
COCONUT IDCNP0182333.1
CAS2392-95-2
InChIKeyJYXSWDCPHRTYGU-RVCYDTIBSA-N
InChIInChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(38-9)39-12-6-13(30)16-14(7-12)40-24(10-2-4-11(29)5-3-10)25(19(16)33)42-27-23(37)21(35)18(32)15(8-28)41-27/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26-,27-/m0/s1
SMILESC[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=C(C4=CC=C(O)C=C4)OC3=C2)[C@H](O)[C@H](O)[C@H]1O

Properties

Molecular FormulaC27H30O15
Molecular Weight594.52
Exact Mass594.15847
Log P (ALogP)-1.74
TPSA249.20
H-Bond Donors / Acceptors9 / 15
Rotatable Bonds6
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.15
NP-likeness1.87

Classification

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

Reported in GR-MAPs Plants

Arabidopsis thaliana as “Arabidopsis thaliana” in COCONUT

References (37)

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  21. 10.1016/j.bmc.2012.12.040
  22. 10.1016/j.phytochem.2005.06.025
  23. 10.1016/j.phytol.2016.08.020
  24. 10.1021/JF9913256
  25. 10.1021/NP0580053
  26. 10.1021/NP200292U
  27. 10.1021/NP800016E
  28. 10.1021/NP990080O
  29. 10.1021/acs.jafc.8b02066
  30. 10.1021/np200292u
  31. 10.1055/S-2006-957620
  32. 10.1080/14786419.2010.537271
  33. 10.1248/CPB.55.1308
  34. 10.1248/CPB.56.1438
  35. 10.1248/CPB.57.1089
  36. 10.1515/ZNC-1990-3-401
  37. 10.3987/COM-08-11385

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.