LIPID MAPS

Structure Database (LMSD)

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Common Name

5beta-cholestanone

Systematic Name

5β-cholestan-3-one

Synonyms

5beta-Cholestan-3-one
5beta-cholestan-3-one
Coprostan-3-one

LM ID

LMST01010205

Formula

C₂₇H₄₆O

Exact Mass

Calculate m/z

386.354866

Sum Composition

ST 27:1;O

Status

Curated

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Classification

Biological Context

5β-Cholestan-3-one is an oxysterol and active metabolite of cholesterol produced by gut microbiota.^1,2 It induces apoptosis in primary dog gallbladder epithelial cells when used at a concentration of 1.4 mM.¹ Fecal levels of 5β-cholestan-3-one are increased in patients with colon cancer or adenomatous polyps.²

This information has been provided by Cayman Chemical

References

1. Seo, D.W., Choi, H.S., Lee, S.P., et al. Oxysterols from human bile induce apoptosis of canine gallbladder epithelial cells in monolayer culture. Am. J. Physiol. Gastrointest. Liver Physiol. 287(6), G1247-G1256 (2004).

2. Reddy, B.S., and Wynder, E.L. Metabolic epidemiology of colon cancer. Fecal bile acids and neutral sterols in colon cancer patients and patients with adenomatous polyps. Cancer 39(6), 2533-2539 (1977).

String Representations

InChiKey (Click to copy)

PESKGJQREUXSRR-JDIFZLMISA-N

InChi (Click to copy)

InChI=1S/C27H46O/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/h18-20,22-25H,6-17H2,1-5H3/t19-,20-,22+,23-,24+,25+,26+,27-/m1/s1

SMILES (Click to copy)

C1CC(=O)C[C@@]2([H])CC[C@]3([H])[C@@]([H])([C@]21C)CC[C@]1(C)[C@@]([H])([C@H](C)CCCC(C)C)CC[C@]13[H]