LIPID MAPS

Structure Database (LMSD)

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Common Name

7alpha-hydroxy-cholesterol(d7)

Systematic Name

cholest-5-en-3β,7α-diol(d7)

Synonyms

LM ID

LMST01010006

Formula

C₂₇H₃₉D₇O₂

Exact Mass

Calculate m/z

409.393718

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

7α-hydroxy Cholesterol-d7 is intended for use as an internal standard for the quantification of 7α-hydroxy cholesterol by GC- or LC-MS. 7α-hydroxy Cholesterol is an oxysterol and a precursor in the biosynthesis of the bile acids cholic acid (CA) and chenodeoxycholic acid (CDCA).^1,2 It is formed via the oxidation of cholesterol by cholesterol 7α-hydroxylase/CYP7A1 in rat liver microsomes.¹ 7α-hydroxy Cholesterol (40 µM) increases levels of the adhesion molecules ICAM-1, VCAM-1, and E-selectin in human umbilical vein endothelial cells (HUVECs).³ It increases secretion of chemokine (C-C motif) ligand 2 (CCL2) and matrix metalloproteinase-9 (MMP-9) in serum-deprived THP-1 cells when used at a concentration of 5 µg/ml.⁴ 7α-hydroxy Cholesterol has been found in macrophages isolated from atherosclerotic lesions in rabbits fed a high-cholesterol diet.⁵

This information has been provided by Cayman Chemical

References

1. Kim, S.M., Kim, B.Y., Son, Y., et al. 7α-Hydroxycholesterol induces inflammation by enhancing production of chemokine (C-C motif) ligand 2. Biochem. Biophys. Res. Commun. 467(4), 879-884 (2015).

2. Mitropoulos, K.A., and Balasubramaniam, S. Cholesterol 7α-hydroxylase in rat liver microsomal preparations. Biochem. J. 128(1), 1-9 (1972).

3. Chiang, J.Y.L. Bile acid metabolism and signaling in liver disease and therapy. Liver Res. 1(1), 3-9 (2017).

4. Lemaire, S., Lizard, G., Monier, S., et al. Different patterns of IL-1β secretion, adhesion molecule expression and apoptosis induction in human endothelial cells treated with 7α-, 7β-hydroxycholesterol, or 7-ketocholesterol. FEBS Lett. 440(3), 434-439 (1998).

5. Hultén, L.M., Lindmark, H., Diczfalusy, U., et al. Oxysterols present in atherosclerotic tissue decrease the expression of lipoprotein lipase messenger RNA in human monocyte-derived macrophages. J. Clin. Invest. 97(2), 461-468 (1996).

References

Comments

Synthetic deuterated standard

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

OYXZMSRRJOYLLO-WCYTWDCFSA-N

InChi (Click to copy)

InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1/i1D3,2D3,17D

SMILES (Click to copy)

[C@]12([C@H](O)C=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCCC(C([2H])([2H])[2H])(C([2H])([2H])[2H])[2H])CC[C@@]21[H])[H]