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COCONUT Compound

(1S,2R,5S,8S,9S,12S,13R,14S,15R,19S,22S,23S,26S,27R)-12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0^{1,17}.0^{2,14}.0^{4,13}.0^{5,9}.0^{19,27}.0^{22,26}]heptacos-3-ene-7,24-dione

CNP0350754.5 · C30H40O6 · View on COCONUT ↗

2D Structure

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Identifiers

Name(1S,2R,5S,8S,9S,12S,13R,14S,15R,19S,22S,23S,26S,27R)-12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0^{1,17}.0^{2,14}.0^{4,13}.0^{5,9}.0^{19,27}.0^{22,26}]heptacos-3-ene-7,24-dione
IUPAC Name(1~{S},2~{R},5~{S},8~{S},9~{S},12~{S},13~{R},14~{S},15~{R},19~{S},22~{S},23~{S},26~{S},27~{R})-12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0^{1,17}.0^{2,14}.0^{4,13}.0^{5,9}.0^{19,27}.0^{22,26}]heptacos-3-ene-7,24-dione
COCONUT IDCNP0350754.5
InChIKeyXDKZYFZYOVAAKJ-GWOGGCNCSA-N
InChIInChI=1S/C30H40O6/c1-12-15-7-9-27(4,33)21-18(22(15)34-25(12)31)14(3)20-19(21)17-11-29(6)30(20)23(17)28(5,36-29)10-8-16-13(2)26(32)35-24(16)30/h12-13,15-17,19-24,33H,7-11H2,1-6H3/t12-,13-,15-,16-,17+,19-,20-,21-,22-,23-,24-,27-,28-,29?,30-/m0/s1
SMILESCC1=C2[C@H]3OC(=O)[C@@H](C)[C@@H]3CC[C@](C)(O)[C@@H]2[C@H]2[C@H]3CC4(C)O[C@@]5(C)CC[C@H]6[C@H](C)C(=O)O[C@@H]6[C@@]4([C@@H]35)[C@@H]12

Properties

Molecular FormulaC30H40O6
Molecular Weight496.64
Exact Mass496.28249
Log P (ALogP)4.04
TPSA82.06
H-Bond Donors / Acceptors1 / 6
Rotatable Bonds0
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.40
NP-likeness2.86

Classification

NP PathwayTerpenoids
NP SuperclassSesquiterpenoids
NP ClassGuaiane sesquiterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassSesterterpenoids

Reported in GR-MAPs Plants

Artemisia annua as “Artemisia annua; Artemisia annua L.” in COCONUT

References (7)

  1. 10.1002/biuz.19840140514
  2. 10.1002/food.19880321030
  3. 10.1016/0031-9422(79)80167-3
  4. 10.1016/S0031-9422(00)83172-6
  5. 10.1016/S0031-9422(98)00762-6
  6. 10.1021/NP000005+
  7. 10.1080/10575630290004260

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.