|
Menu

COCONUT Compound

(22E,24S)-5alpha,8alpha-epidioxy-24-methylcholesta-6,22-dien-3beta-ol

CNP0249383.7 · C28H44O3 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

Name(22E,24S)-5alpha,8alpha-epidioxy-24-methylcholesta-6,22-dien-3beta-ol
IUPAC Name(1~{S},2~{R},5~{R},6~{R},9~{R},10~{R},13~{S},15~{S})-6,10-dimethyl-5-[(~{E},1~{R},4~{S})-1,4,5-trimethylhex-2-enyl]-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadec-18-en-13-ol
COCONUT IDCNP0249383.7
InChIKeyVXOZCESVZIRHCJ-LBMRXTFASA-N
InChIInChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+/t19-,20-,21+,22-,23-,24-,25-,26-,27-,28+/m1/s1
SMILESCC(C)[C@H](C)/C=C/[C@@H](C)[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@]23C=C[C@]2(C[C@@H](O)CC[C@]12C)OO3

Properties

Molecular FormulaC28H44O3
Molecular Weight428.66
Exact Mass428.32905
Log P (ALogP)6.47
TPSA38.69
H-Bond Donors / Acceptors1 / 3
Rotatable Bonds4
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.41
NP-likeness3.36

Classification

NP PathwayTerpenoids
NP SuperclassSteroids
NP ClassCholestane steroids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassSteroids and steroid derivatives
Chemical SubclassErgostane steroids

Reported in GR-MAPs Plants

Foeniculum vulgare as “Foeniculum vulgare” in COCONUT

References (9)

  1. 10.1016/0031-9422(83)85062-6
  2. 10.1016/J.BMCL.2010.05.061
  3. 10.1016/J.PHYTOCHEM.2007.03.029
  4. 10.1016/J.STEROIDS.2008.09.007
  5. 10.1016/S0031-9422(00)97583-6
  6. 10.1021/NP100566V
  7. 10.1021/np100566v
  8. 10.1139/V92-286
  9. 10.1248/CPB.50.1603

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.