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COCONUT Compound

Secoxyloganin

CNP0121282.1 · C17H24O11 · View on COCONUT ↗

2D Structure

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Identifiers

NameSecoxyloganin
IUPAC Name2-[(2~{S},3~{R},4~{S})-5-methoxycarbonyl-2-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-vinyl-3,4-dihydro-2~{H}-pyran-4-yl]acetic acid
COCONUT IDCNP0121282.1
CAS58822-47-2
InChIKeyMQLSOVRLZHTATK-PEYNGXJCSA-N
InChIInChI=1S/C17H24O11/c1-3-7-8(4-11(19)20)9(15(24)25-2)6-26-16(7)28-17-14(23)13(22)12(21)10(5-18)27-17/h3,6-8,10,12-14,16-18,21-23H,1,4-5H2,2H3,(H,19,20)/t7-,8+,10-,12-,13+,14-,16+,17+/m1/s1
SMILESC=C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)O

Properties

Molecular FormulaC17H24O11
Molecular Weight404.37
Exact Mass404.13186
Log P (ALogP)-1.89
TPSA172.21
H-Bond Donors / Acceptors5 / 10
Rotatable Bonds7
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.24
NP-likeness2.57

Classification

NP PathwayTerpenoids
NP SuperclassMonoterpenoids
NP ClassSecoiridoid monoterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassMonoterpenoids

Reported in GR-MAPs Plants

Catharanthus roseus as “Catharanthus roseus” in COCONUT
Rauvolfia serpentina as “Rauwolfia serpentina” in COCONUT

References (38)

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  22. 10.1021/NP058062W
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  25. 10.1055/S-2006-961403
  26. 10.1076/PHBI.34.4.255.13230
  27. 10.1080/14786419.2012.761616
  28. 10.1186/S12864-015-1678-Y
  29. 10.1186/s12864-015-1678-y
  30. 10.1248/BPB.34.1330
  31. 10.1248/bpb.34.1330
  32. 10.1371/JOURNAL.PONE.0096214
  33. 10.1515/ZNC-2015-0036
  34. 10.1515/znc-2015-0036
  35. 10.2174/1871520614666140804153936
  36. 10.3390/MOLECULES21091157
  37. 10.3390/molecules21091157
  38. 10.3987/COM-09-11886

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.