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COCONUT Compound

Isorhoifolin

CNP0223007.2 · C27H30O14 · View on COCONUT ↗

2D Structure

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Identifiers

NameIsorhoifolin
IUPAC Name5-hydroxy-2-(4-hydroxyphenyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
COCONUT IDCNP0223007.2
CAS552-57-8, 36790-49-5
InChIKeyFKIYLTVJPDLUDL-SLNHTJRHSA-N
InChIInChI=1S/C27H30O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-8,10,18,20-29,31-36H,9H2,1H3/t10-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
SMILESC[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)C=C(C5=CC=C(O)C=C5)OC4=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

Properties

Molecular FormulaC27H30O14
Molecular Weight578.52
Exact Mass578.16356
Log P (ALogP)-1.10
TPSA228.97
H-Bond Donors / Acceptors8 / 14
Rotatable Bonds6
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.17
NP-likeness1.84

Classification

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

Reported in GR-MAPs Plants

Mentha piperita as “Mentha piperita; Mentha X piperita” in COCONUT
Daucus carota as “Daucus carota” in COCONUT
Mentha Arvensis as “Mentha arvensis” in COCONUT

References (35)

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  6. 10.1016/0031-9422(75)85211-3
  7. 10.1016/0031-9422(86)88052-9
  8. 10.1016/0305-1978(94)90062-0
  9. 10.1016/0305-1978(94)90075-2
  10. 10.1016/J.BMCL.2011.03.078
  11. 10.1016/J.BSE.2011.12.023
  12. 10.1016/J.PHYTOCHEM.2010.08.009
  13. 10.1016/S0031-9422(00)00355-1
  14. 10.1016/S0031-9422(00)84593-8
  15. 10.1016/S0031-9422(99)00584-1
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  18. 10.1016/S0378-8741(99)00169-5
  19. 10.1016/S0968-0896(02)00470-4
  20. 10.1016/j.bmcl.2011.03.078
  21. 10.1016/j.bse.2011.12.023
  22. 10.1016/s0044-328x(80)80076-6
  23. 10.1021/JF040214Q
  24. 10.1021/JF048484W
  25. 10.1021/acs.jnatprod.8b00948
  26. 10.1055/S-2006-958024
  27. 10.1080/10826079208016365
  28. 10.1248/BPB.25.256
  29. 10.1248/CPB.52.612
  30. 10.1248/CPB.53.1416
  31. 10.1248/YAKUSHI1947.105.6_542
  32. 10.1515/ZNC-2001-7-808
  33. 10.21608/BFSA.2002.65703
  34. 10.3797/SCIPHARM.AUT-01-09
  35. 10.5772/INTECHOPEN.75648

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.