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COCONUT Compound

Isoacteoside

CNP0288601.3 · C29H36O15 · View on COCONUT ↗

2D Structure

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Identifiers

NameIsoacteoside
IUPAC Name[(2~{R},3~{R},4~{S},5~{R},6~{R})-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]methyl (~{E})-3-(3,4-dihydroxyphenyl)prop-2-enoate
COCONUT IDCNP0288601.3
CAS61303-13-7
InChIKeyFNMHEHXNBNCPCI-QEOJJFGVSA-N
InChIInChI=1S/C29H36O15/c1-13-22(35)24(37)25(38)29(42-13)44-27-23(36)20(12-41-21(34)7-4-14-2-5-16(30)18(32)10-14)43-28(26(27)39)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27-,28+,29-/m0/s1
SMILESC[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OCCC3=CC=C(O)C(O)=C3)O[C@H](COC(=O)/C=C/C3=CC=C(O)C(O)=C3)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O

Properties

Molecular FormulaC29H36O15
Molecular Weight624.59
Exact Mass624.20542
Log P (ALogP)-1.02
TPSA245.29
H-Bond Donors / Acceptors9 / 15
Rotatable Bonds10
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.09
NP-likeness1.70

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassPhenylethanoids (C6-C2)
NP ClassCinnamic acids and derivatives
Chemical SuperclassPhenylpropanoids and polyketides
Chemical ClassCinnamic acids and derivatives
Chemical SubclassHydroxycinnamic acids and derivatives

Reported in GR-MAPs Plants

Callicarpa macrophylla as “Callicarpa macrophylla” in COCONUT
Acorus calamus as “Acorus calamus” in COCONUT

References (65)

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  3. 10.1002/JSSC.201200010
  4. 10.1002/JSSC.201300794
  5. 10.1007/S10600-011-9920-6
  6. 10.1007/S10600-012-0123-6
  7. 10.1007/S11418-006-0043-5
  8. 10.1007/S11418-009-0383-Z
  9. 10.1016/0031-9422(93)85348-U
  10. 10.1016/0031-9422(96)00158-6
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  12. 10.1016/J.BMC.2006.07.018
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  14. 10.1016/J.FITOTE.2011.10.003
  15. 10.1016/J.FITOTE.2011.12.025
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  17. 10.1016/J.JPBA.2019.03.044
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  19. 10.1016/J.PHYTOCHEM.2007.02.002
  20. 10.1016/J.PHYTOCHEM.2008.07.002
  21. 10.1016/J.PHYTOCHEM.2015.02.020
  22. 10.1016/S0031-9422(00)00306-X
  23. 10.1016/S0031-9422(00)95007-6
  24. 10.1016/S0031-9422(00)95234-8
  25. 10.1016/S0031-9422(01)00208-4
  26. 10.1016/S0031-9422(01)00212-6
  27. 10.1016/S0031-9422(01)00306-5
  28. 10.1016/S0031-9422(01)00466-6
  29. 10.1016/S0031-9422(01)00476-9
  30. 10.1016/S0031-9422(98)00538-X
  31. 10.1016/S0031-9422(99)00167-3
  32. 10.1016/j.bmc.2010.01.047
  33. 10.1016/j.fitote.2011.12.025
  34. 10.1021/JF0479867
  35. 10.1021/JF801603S
  36. 10.1021/NP0003591
  37. 10.1021/NP0100845
  38. 10.1021/NP040006S
  39. 10.1021/NP0501233
  40. 10.1021/NP0501233.S001

Showing 40 of 65. See all references on 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.