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COCONUT Compound

(-)-Lyoniresinol 9'-O-glucoside

CNP0210130.2 · C28H38O13 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

Name(-)-Lyoniresinol 9'-O-glucoside
IUPAC Name(2~{R},3~{R},4~{S},5~{S},6~{R})-2-[[(1~{R},2~{S},3~{S})-7-hydroxy-1-(4-hydroxy-3,5-dimethoxy-phenyl)-3-(hydroxymethyl)-6,8-dimethoxy-tetralin-2-yl]methoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
COCONUT IDCNP0210130.2
CAS143236-02-6
InChIKeyPQQRNPDHSJDAGV-UGJKOEBBSA-N
InChIInChI=1S/C28H38O13/c1-36-16-7-13(8-17(37-2)22(16)31)20-15(11-40-28-26(35)25(34)23(32)19(10-30)41-28)14(9-29)5-12-6-18(38-3)24(33)27(39-4)21(12)20/h6-8,14-15,19-20,23,25-26,28-35H,5,9-11H2,1-4H3/t14-,15-,19-,20+,23-,25+,26-,28-/m1/s1
SMILESCOC1=CC([C@@H]2C3=C(OC)C(O)=C(OC)C=C3C[C@H](CO)[C@H]2CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1O

Properties

Molecular FormulaC28H38O13
Molecular Weight582.60
Exact Mass582.23124
Log P (ALogP)-0.14
TPSA196.99
H-Bond Donors / Acceptors7 / 13
Rotatable Bonds10
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.20
NP-likeness1.96

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassLignans
NP ClassArylnaphthalene and aryltetralin lignans
Chemical SuperclassLignans, neolignans and related compounds
Chemical ClassLignan glycosides
Chemical SubclassLignan glycosides

Reported in GR-MAPs Plants

Vitex negundo as “Vitex negundo” in COCONUT

References (12)

  1. 10.1016/J.PHYTOCHEM.2009.07.013
  2. 10.1016/J.PHYTOCHEM.2015.02.020
  3. 10.1016/S0031-9422(01)00306-5
  4. 10.1016/S0031-9422(96)00879-5
  5. 10.1016/S0960-894X(98)00528-9
  6. 10.1016/j.phytochem.2015.02.020
  7. 10.1016/s0031-9422(01)00306-5
  8. 10.1080/10286020.2016.1142975
  9. 10.1080/14786410902819152
  10. 10.1248/CPB.42.1924
  11. 10.1590/S0100-46702006000400008
  12. 10.1590/S0103-50532007000700017

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.