LIPID MAPS

Structure Database (LMSD)

Download as... MDLMOL SDF CSV TSV PNG SVG

Systematic Name

3β-hydroxy-stigmast-5-en-7-one

Synonyms

LM ID

LMST01040169

Formula

C₂₉H₄₈O₂

Exact Mass

Calculate m/z

428.365431

Sum Composition

ST 29:2;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

7-Ketositosterol is a phytosterol and phytosterol oxidation product (POP).^1,2 It is a thermal oxidation product of sitosterol (24α-ethyl cholesterol).² 7-Ketositosterol inhibits the proliferation of HL-60 acute myeloid leukemia (AML) cells (IC50 = 45.6 µM).³

This information has been provided by Cayman Chemical

References

1. McDonald, K., Langenbahn, H.J., Miller, J.D., et al. Phytosterol oxidation products from coffee silverskin. J. Food Sci. 87(2), 728-737 (2022).

2. Oyama, M., Tokiwano, T., Ota, H., et al. β-sitosterol oxides from the dried stem of salix gilgiana inhibit the proliferation of HL-60 leukemic cells. Curr. Bioact. Compd. 16(3), 329-334 (2020).

3. Yu, J.-D., Chen, M.-X., Wu, H., et al. Phytochemical and chemotaxonomic study on Pholidota pallida lindl. Biochem. Syst. Ecol. 97, 104290 (2021).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Fucus evanescens (#87147)

Phaeophyceae (#2870)

Marine Sterols,
Nat Prod Rep, 1991

DOI: 10.1039/NP9910800465

String Representations

InChiKey (Click to copy)

ICFXJOAKQGDRCT-ZIHMWMKCSA-N

InChi (Click to copy)

InChI=1S/C29H48O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-27-25(13-15-29(23,24)6)28(5)14-12-22(30)16-21(28)17-26(27)31/h17-20,22-25,27,30H,7-16H2,1-6H3/t19-,20-,22+,23-,24+,25+,27+,28+,29-/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CC[C@@H](CC)C(C)C)CC[C@@]4([H])[C@]3([H])C(=O)C=C2C[C@@H](O)C1