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COCONUT Compound

5,7-dihydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-[(2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

CNP0306137.1 · C27H30O15 · View on COCONUT ↗

2D Structure

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Identifiers

Name5,7-dihydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-[(2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
IUPAC Name5,7-dihydroxy-3-(4-hydroxyphenyl)-8-[(2~{S},3~{R},5~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]-6-[(2~{S},4~{R},5~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one
COCONUT IDCNP0306137.1
InChIKeyISNRVVKKHPECQN-UIPWJEGLSA-N
InChIInChI=1S/C27H30O15/c28-5-11-17(32)21(36)23(38)26(41-11)14-19(34)13-16(31)10(8-1-3-9(30)4-2-8)7-40-25(13)15(20(14)35)27-24(39)22(37)18(33)12(6-29)42-27/h1-4,7,11-12,17-18,21-24,26-30,32-39H,5-6H2/t11?,12?,17-,18-,21+,22?,23?,24-,26+,27+/m1/s1
SMILESO=C1C(C2=CC=C(O)C=C2)=COC2=C([C@@H]3OC(CO)[C@@H](O)C(O)[C@H]3O)C(O)=C([C@@H]3OC(CO)[C@@H](O)[C@H](O)C3O)C(O)=C12

Properties

Molecular FormulaC27H30O15
Molecular Weight594.52
Exact Mass594.15847
Log P (ALogP)-2.39
TPSA271.20
H-Bond Donors / Acceptors11 / 15
Rotatable Bonds5
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.15
NP-likeness1.52

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassIsoflavonoids
NP ClassIsoflavones
Chemical SuperclassPhenylpropanoids and polyketides
Chemical ClassIsoflavonoids
Chemical SubclassIsoflavonoid C-glycosides

Reported in GR-MAPs Plants

Andrographis paniculata as “Andrographis paniculata” in COCONUT

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.