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Structure Database (LMSD)

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Common Name

Coprostanol

Systematic Name

5β-cholestan-3β-ol

Synonyms

Coprosterol

LM ID

LMST01010078

Formula

C₂₇H₄₈O

Exact Mass

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388.370515

Sum Composition

ST 27:0;O

Status

Curated

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Classification

Biological Context

Coprostanol is a cholesterol derivative formed in mammals by intestinal microorganisms and is the odorous compound in feces.¹ It is formed via conversion of cholesterol to cholestenone then coprostanone intermediates or by direct reduction of the 5,6 double bond. Coprostanol is commonly used as a marker of sewage contamination in soil and watersheds.^2,3

This information has been provided by Cayman Chemical

References

1. Ren, D., Li, L., Schwabacher, A.W., et al. Mechanism of cholesterol reduction to coprostanol by Eubacterium coprostanoligenes ATCC 51222. Steroids 61(1), 33-40 (1996).

2. von der Lühe, B., Dawson, L.A., Mayes, R.W., et al. Investigation of sterols as potential biomarkers for the detection of pig (S. s. domesticus) decomposition fluid in soils. Forensic Sci. Int. 230(1-3), 68-73 (2013).

3. Nichols, P.D., Leeming, R., Rayner, M.S., et al. Comparison of the abundance of the fecal sterol coprostanol and fecal bacterial groups in inner-shelf waters and sediments near Sydney, Australia. J. Chromatogr. 643(1-2), 189-195 (1993).

String Representations

InChiKey (Click to copy)

QYIXCDOBOSTCEI-NWKZBHTNSA-N

InChi (Click to copy)

InChI=1S/C27H48O/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/h18-25,28H,6-17H2,1-5H3/t19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

SMILES (Click to copy)

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