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COCONUT Compound

Asperuloside

CNP0247031.2 · C18H22O11 · View on COCONUT ↗

2D Structure

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Identifiers

NameAsperuloside
IUPAC Name[(4~{S},7~{S},8~{S},11~{S})-2-oxo-8-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3,9-dioxatricyclo[5.3.1.0^{4,11}]undeca-1(10),5-dien-6-yl]methyl acetate
COCONUT IDCNP0247031.2
CAS14259-45-1
InChIKeyIBIPGYWNOBGEMH-DILZHRMZSA-N
InChIInChI=1S/C18H22O11/c1-6(20)25-4-7-2-9-12-8(16(24)27-9)5-26-17(11(7)12)29-18-15(23)14(22)13(21)10(3-19)28-18/h2,5,9-15,17-19,21-23H,3-4H2,1H3/t9-,10+,11+,12-,13+,14-,15+,17-,18-/m0/s1
SMILESCC(=O)OCC1=C[C@@H]2OC(=O)C3=CO[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H]1[C@@H]32

Properties

Molecular FormulaC18H22O11
Molecular Weight414.36
Exact Mass414.11621
Log P (ALogP)-2.30
TPSA161.21
H-Bond Donors / Acceptors4 / 11
Rotatable Bonds5
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.28
NP-likeness2.86

Classification

NP PathwayTerpenoids
NP SuperclassMonoterpenoids
NP ClassIridoids monoterpenoids
Chemical SuperclassOrganoheterocyclic compounds
Chemical ClassFuropyrans
Chemical SubclassFuropyrans

Reported in GR-MAPs Plants

Plantago ovata as “Plantago ovata” in COCONUT

References (51)

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  2. 10.1002/CHIN.200927180
  3. 10.1002/HLCA.19810640748
  4. 10.1002/HLCA.200900158
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  11. 10.1016/0305-1978(89)90101-4
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  20. 10.1016/S0031-9422(02)00096-1
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  22. 10.1016/S0031-9422(97)01121-7
  23. 10.1016/S0305-1978(01)00135-1
  24. 10.1021/NP000614H
  25. 10.1021/NP010011L
  26. 10.1021/NP0495985
  27. 10.1021/NP0495985.S001
  28. 10.1021/NP050181O
  29. 10.1021/NP060515P
  30. 10.1021/NP070116+
  31. 10.1021/NP0780046
  32. 10.1021/NP50026A002
  33. 10.1021/NP50035A033
  34. 10.1021/OL990811B
  35. 10.1021/acs.jnatprod.6b00484
  36. 10.1039/p19760001789
  37. 10.1055/S-2000-8544
  38. 10.1080/01483918408074076
  39. 10.1081/JLC-100101486
  40. 10.1248/CPB.39.2049

Showing 40 of 51. 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.