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COCONUT Compound

27-Hydroxywithanone

CNP0122501.1 · C28H38O7 · View on COCONUT ↗

2D Structure

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Identifiers

Name27-Hydroxywithanone
IUPAC Name(1~{S},2~{S},4~{S},5~{R},10~{R},11~{S},14~{S},15~{S},18~{S})-5,15-dihydroxy-15-[(1~{R})-1-[(2~{R})-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10,14-dimethyl-3-oxapentacyclo[9.7.0.0^{2,4}.0^{5,10}.0^{14,18}]octadec-7-en-9-one
COCONUT IDCNP0122501.1
CAS871949-32-5
InChIKeyXOKCBESGXYESDY-LGZUTLPBSA-N
InChIInChI=1S/C28H38O7/c1-14-12-19(34-24(31)16(14)13-29)15(2)27(32)11-8-17-21-18(7-10-25(17,27)3)26(4)20(30)6-5-9-28(26,33)23-22(21)35-23/h5-6,15,17-19,21-23,29,32-33H,7-13H2,1-4H3/t15-,17+,18+,19-,21+,22+,23+,25+,26+,27+,28+/m1/s1
SMILESCC1=C(CO)C(=O)O[C@@H]([C@@H](C)[C@@]2(O)CC[C@H]3[C@@H]4[C@@H]5O[C@@H]5[C@@]5(O)CC=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1

Properties

Molecular FormulaC28H38O7
Molecular Weight486.61
Exact Mass486.26175
Log P (ALogP)2.47
TPSA116.59
H-Bond Donors / Acceptors3 / 7
Rotatable Bonds3
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.41
NP-likeness3.55

Classification

NP PathwayTerpenoids
NP SuperclassSteroids
NP ClassErgostane steroids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassSteroids and steroid derivatives
Chemical SubclassSteroid lactones

Reported in GR-MAPs Plants

Withania somnifera as “Withania somnifera” in COCONUT

References (6)

  1. 10.1007/S10870-011-0047-1
  2. 10.1016/J.LFS.2007.01.029
  3. 10.1016/J.PHYTOCHEM.2005.10.001
  4. 10.1016/J.PHYTOCHEM.2006.07.014
  5. 10.1016/J.PHYTOCHEM.2010.04.001
  6. 10.1021/acs.jnatprod.8b00665

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.