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COCONUT Compound

(2~{S},3~{S})-2-(3,4-dihydroxyphenyl)-6-[(~{E})-2-(3,4-dihydroxyphenyl)vinyl]-5'-methyl-spiro[2~{H}-furo[3,2-c]pyran-3,2'-furan]-3',4-dione

CNP0185875.1 · C25H18O9 · View on COCONUT ↗

2D Structure

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Identifiers

IUPAC Name(2~{S},3~{S})-2-(3,4-dihydroxyphenyl)-6-[(~{E})-2-(3,4-dihydroxyphenyl)vinyl]-5'-methyl-spiro[2~{H}-furo[3,2-c]pyran-3,2'-furan]-3',4-dione
COCONUT IDCNP0185875.1
InChIKeyZGKUEJPXTILOCD-YXGSLQHTSA-N
InChIInChI=1S/C25H18O9/c1-12-8-21(30)25(34-12)22-20(33-23(25)14-4-7-17(27)19(29)10-14)11-15(32-24(22)31)5-2-13-3-6-16(26)18(28)9-13/h2-11,23,26-29H,1H3/b5-2+/t23-,25-/m0/s1
SMILESCC1=CC(=O)[C@]2(O1)C1=C(C=C(/C=C/C3=CC=C(O)C(O)=C3)OC1=O)O[C@H]2C1=CC=C(O)C(O)=C1

Properties

Molecular FormulaC25H18O9
Molecular Weight462.41
Exact Mass462.09508
Log P (ALogP)3.46
TPSA146.66
H-Bond Donors / Acceptors4 / 9
Rotatable Bonds3
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.43
NP-likeness1.77

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassStyrylpyrones
NP ClassKavalactones and derivatives
Chemical SuperclassOrganoheterocyclic compounds
Chemical ClassPyrans
Chemical SubclassPyranones and derivatives

Reported in GR-MAPs Plants

Mentha piperita as “Mentha X piperita” in COCONUT
Commiphora wightii as “Commiphora mukul” in COCONUT

References (6)

  1. 10.1007/S11418-008-0260-1
  2. 10.1016/J.BMCL.2010.07.093
  3. 10.1016/S0040-4039(99)01406-9
  4. 10.1021/NP030505D
  5. 10.1021/NP050453N
  6. 10.1038/BJP.2008.136

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.