LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG SVG

Common Name

7alpha-hydroxy-cholesterol

Systematic Name

cholest-5-en-3β,7α-diol

Synonyms

LM ID

LMST01010013

Formula

C₂₇H₄₆O₂

Exact Mass

Calculate m/z

402.349781

Sum Composition

ST 27:1;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

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. 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).

2. 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).

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

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

5. 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).

Reactions

Filter by species:

Click on an edge to display the reaction(s).

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)

OYXZMSRRJOYLLO-RVOWOUOISA-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

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)C)CC[C@@]21[H])[H]