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COCONUT Compound

3-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

CNP0263713.1 · C27H30O17 · View on COCONUT ↗

2D Structure

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Identifiers

Name3-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
IUPAC Name3-[(2~{S},3~{R},4~{R},5~{S},6~{R})-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one
COCONUT IDCNP0263713.1
InChIKeyUTECWQIXBMWRRR-QXHWVZJPSA-N
InChIInChI=1S/C27H30O17/c28-6-14-17(34)19(36)21(38)26(41-14)43-24-15(7-29)42-27(22(39)20(24)37)44-25-18(35)16-12(33)4-9(30)5-13(16)40-23(25)8-1-2-10(31)11(32)3-8/h1-5,14-15,17,19-22,24,26-34,36-39H,6-7H2/t14-,15-,17-,19+,20-,21-,22-,24-,26+,27+/m1/s1
SMILESO=C1C(O[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)=C(C2=CC=C(O)C(O)=C2)OC2=CC(O)=CC(O)=C12

Properties

Molecular FormulaC27H30O17
Molecular Weight626.52
Exact Mass626.14830
Log P (ALogP)-2.71
TPSA289.66
H-Bond Donors / Acceptors11 / 17
Rotatable Bonds7
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.12
NP-likeness1.98

Classification

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

Reported in GR-MAPs Plants

Hibiscus rosa-sinensis as “Hibiscus rosa-sinensis” in COCONUT
Gossypium hirsutum as “Gossypium hirsutum” in COCONUT

References (6)

  1. 10.1016/0031-9422(81)84073-3
  2. 10.1016/0305-1978(84)90032-2
  3. 10.1016/0305-1978(94)90048-5
  4. 10.1016/S0031-9422(00)97883-X
  5. 10.1021/JF60229A021
  6. 10.1021/NP1000818

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.