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Structure Database (LMSD)

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Common Name

Cholestenone

Systematic Name

cholest-4-en-3-one

Synonyms

Cholestenone (delta 4)

LM ID

LMST01010015

Formula

C₂₇H₄₄O

Exact Mass

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384.339215

Sum Composition

ST 27:2;O

Status

Curated

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Classification

Biological Context

Cholestanone is a cholesterol metabolite that has a keto group in place of the 3-hydroxy group on cholesterol.¹ It decreases TGF-β-induced Smad2 phosphorylation and TGF-β expression and prevents inhibition of DNA synthesis by TGF-β in Mv1Lu cells when used at a concentration of 50 µg/ml.² Increased fecal excretion of cholestenone is correlated with an increased risk of colorectal cancer. Cholestenone reduces serum cholesterol levels in a variety of animal models but is toxic to rats when administered at doses of 700-1,000 mg/kg per day, inducing hypertrophy in and reducing the activity of the adrenal gland.³ It has been used as synthetic intermediate in the synthesis of steroids.⁴

This information has been provided by Cayman Chemical

References

1. Salen, G., Batta, A.K., Tint, G.S., et al. Inverse relationship between plasma cholestanol concentrations and bile acid synthesis in sitosterolemia. J. Lipid Res. 35(10), 1878-1887 (1994).

2. Chen, C.-L., Wu, D.-C., Liu, M.-Y., et al. Cholest-4-en-3-one attenuates TGF-β responsiveness by inducing TGF-β receptors degradation in Mv1Lu cells and colorectal adenocarcinoma cells. J. Recept. Signal Transduct. Res. 37(2), 189-199 (2017).

3. Steinberg, D., Fredrickson, D.S., and Avigan, J. Effects of Δ4-cholestenone in animals and in man. Proc. Soc. Exp. Biol. Med. 97(4), 784-790 (1958).

4. Wu, K., Li, W., Song, J., et al. Production, purification, and identification of cholest-4-en-3-one produced by cholesterol oxidase from Rhodococcus sp. in aqueous/organic biphasic system. Biochem. Insights 8(Suppl 1), 1-8 (2015).

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

Mus musculus (#10090)

Mammalia (#40674)

Subcellular organelle lipidomics in TLR-4-activated macrophages.,
J Lipid Res, 2010

Pubmed ID: 20574076

DOI: 10.1194/jlr.M008748

String Representations

InChiKey (Click to copy)

NYOXRYYXRWJDKP-GYKMGIIDSA-N

InChi (Click to copy)

InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

SMILES (Click to copy)

[C@]12(CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCCC(C)C)CC[C@@]21[H])[H]