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COCONUT Compound

Forsythoside B

CNP0249576.1 · C34H44O19 · View on COCONUT ↗

2D Structure

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Identifiers

NameForsythoside B
IUPAC Name[(2~{R},3~{R},4~{R},5~{R},6~{R})-2-[[(2~{R},3~{R},4~{R})-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]oxymethyl]-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-4-[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl] (~{E})-3-(3,4-dihydroxyphenyl)prop-2-enoate
COCONUT IDCNP0249576.1
CAS81525-13-5
InChIKeyJMBINOWGIHWPJI-UNSOMVRXSA-N
InChIInChI=1S/C34H44O19/c1-15-24(41)25(42)26(43)32(50-15)53-29-27(44)31(47-9-8-17-3-6-19(37)21(39)11-17)51-22(12-48-33-30(45)34(46,13-35)14-49-33)28(29)52-23(40)7-4-16-2-5-18(36)20(38)10-16/h2-7,10-11,15,22,24-33,35-39,41-46H,8-9,12-14H2,1H3/b7-4+/t15-,22+,24-,25+,26+,27+,28+,29+,30-,31+,32-,33+,34+/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](CO[C@@H]3OC[C@](O)(CO)[C@H]3O)[C@H]2OC(=O)/C=C/C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O)[C@H]1O

Properties

Molecular FormulaC34H44O19
Molecular Weight756.71
Exact Mass756.24768
Log P (ALogP)-2.55
TPSA304.21
H-Bond Donors / Acceptors11 / 19
Rotatable Bonds13
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.06
NP-likeness1.99

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
Nepeta cataria as “Nepeta cataria” in COCONUT

References (37)

  1. 10.1002/(SICI)1099-1573(200003)14:2<93::AID-PTR558>3.0.CO;2-X
  2. 10.1002/9780470514344.CH14
  3. 10.1002/CHIN.200301194
  4. 10.1002/CHIN.200352191
  5. 10.1002/HLCA.200790007
  6. 10.1002/JSSC.201300268
  7. 10.1002/RCM.2875
  8. 10.1007/S11418-007-0135-X
  9. 10.1007/s11418-012-0658-7
  10. 10.1016/0031-9422(92)80032-A
  11. 10.1016/0031-9422(92)80178-H
  12. 10.1016/0031-9422(92)80194-J
  13. 10.1016/0031-9422(92)83740-P
  14. 10.1016/0031-9422(96)00322-6
  15. 10.1016/J.JEP.2007.11.044
  16. 10.1016/J.PHYTOCHEM.2007.02.002
  17. 10.1016/S0031-9422(00)89516-3
  18. 10.1016/S0031-9422(01)00236-9
  19. 10.1016/S0031-9422(03)00242-5
  20. 10.1016/S0031-9422(96)00446-3
  21. 10.1016/S0031-9422(96)00578-X
  22. 10.1016/S0378-8741(01)00415-9
  23. 10.1016/S0378-8741(99)00019-7
  24. 10.1021/NP060499W
  25. 10.1021/NP50043A037
  26. 10.1021/NP50055A033
  27. 10.1021/NP990092+
  28. 10.1055/S-0031-1282534
  29. 10.1055/S-0031-1300158
  30. 10.1055/S-2004-827200
  31. 10.1055/S-2006-957854
  32. 10.1055/S-2006-960215
  33. 10.1248/BPB.18.1396
  34. 10.1248/CPB.49.1039
  35. 10.1515/ZNC-2001-9-1004
  36. 10.3987/R-1982-02-0261
  37. 10.4268/CJCMM20141019

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.