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COCONUT Compound

Homoplantaginin

CNP0199272.1 · C22H22O11 · View on COCONUT ↗

2D Structure

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Identifiers

NameHomoplantaginin
IUPAC Name5-hydroxy-2-(4-hydroxyphenyl)-6-methoxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
COCONUT IDCNP0199272.1
CAS17680-84-1
InChIKeyGCLAFEGUXXHIFT-IWLDQSELSA-N
InChIInChI=1S/C22H22O11/c1-30-21-14(32-22-20(29)19(28)17(26)15(8-23)33-22)7-13-16(18(21)27)11(25)6-12(31-13)9-2-4-10(24)5-3-9/h2-7,15,17,19-20,22-24,26-29H,8H2,1H3/t15-,17-,19+,20-,22-/m1/s1
SMILESCOC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C2OC(C3=CC=C(O)C=C3)=CC(=O)C2=C1O

Properties

Molecular FormulaC22H22O11
Molecular Weight462.41
Exact Mass462.11621
Log P (ALogP)0.06
TPSA179.28
H-Bond Donors / Acceptors6 / 11
Rotatable Bonds5
Lipinski's Rule of 5 Violations2
QED Drug-likeness0.30
NP-likeness1.96

Classification

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

Reported in GR-MAPs Plants

Rosmarinus officinalis as “Rosmarinus officinalis” in COCONUT
Salvia officinalis as “Salvia officinalis” in COCONUT

References (29)

  1. 10.1007/s10600-014-0840-0
  2. 10.1016/0031-9422(88)80043-8
  3. 10.1016/0031-9422(88)87035-3
  4. 10.1016/0031-9422(95)00206-M
  5. 10.1016/0378-8741(85)90026-1
  6. 10.1016/J.CARRES.2010.09.002
  7. 10.1016/J.PHYTOCHEM.2007.04.014
  8. 10.1016/J.PHYTOCHEM.2007.11.014
  9. 10.1016/S0031-9422(00)84935-3
  10. 10.1016/S0031-9422(00)89581-3
  11. 10.1016/S0031-9422(01)00212-6
  12. 10.1016/S0031-9422(02)00218-2
  13. 10.1016/S0305-1978(02)00219-3
  14. 10.1016/j.sajb.2014.06.003
  15. 10.1021/JF040078P
  16. 10.1021/JF980614B
  17. 10.1021/NP040175C
  18. 10.1021/NP500150F
  19. 10.1021/NP50122A015
  20. 10.1021/NP990271R
  21. 10.1021/np500150f
  22. 10.1021/np990271r
  23. 10.1055/S-2007-969135
  24. 10.1055/S-2007-987153
  25. 10.1080/14786410802696247
  26. 10.1086/325089
  27. 10.1248/CPB.55.1635
  28. 10.3390/MOLECULES21111576
  29. 10.4314/ajtcam.v5i1.31251

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.