LIPID MAPS

Structure Database (LMSD)

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Common Name

7-dehydrocholesterol

Systematic Name

cholesta-5,7-dien-3β-ol

Synonyms

7-DHC

LM ID

LMST01010069

Formula

C₂₇H₄₄O

Exact Mass

Calculate m/z

384.339215

Sum Composition

ST 27:2;O

Status

Curated

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Classification

Biological Context

7-dehydro Cholesterol (7-DHC) is an immediate precursor of cholesterol.¹ It is reduced to cholesterol by the enzyme 3β-hydroxysterol-Δ7-reductase (DHCR7) in the last step of cholesterol biosynthesis. 7-DHC accumulates in Smith-Lemli-Opitz syndrome (SLOS), a disorder characterized by a mutation in the DHCR7 gene and decreased cholesterol levels in bodily tissues and fluids, as well as microcephaly, intellectual disability, and distinctive dysmorphic features.^1,2 It is highly susceptible to free radical oxidation, giving rise to several oxysterols that may be involved in the pathogenesis of SLOS.¹ 7-DHC levels are increased in brain, liver, and serum in a rat model of SLOS induced by the DHCR7 inhibitor AY 9944 .¹ 7-DHC is a provitamin that is converted to vitamin D3 by ultraviolet-B (UVB) light in a human skin equivalent system and in isolated human skin samples.^3,4

This information has been provided by Cayman Chemical

References

1. Xu, L., Liu, W., Sheflin, L.G., et al. Novel oxysterols observed in tissues and fluids of AY9944-treated rats: A model for Smith-Lemli-Opitz syndrome. J. Lipid Res. 52, 1810-1820 (2011).

2. Lehmann, B., Genehr, T., Knuschke, P., et al. UVB-induced conversion of 7-dehydrocholesterol to 1α,25-dihydroxyvitamin D3 in an in vitro human skin equivalent model. J. Invest. Dermatol. 117(5), 1179-1185 (2001).

3. Chen, T.C., Chimeh, F., Lu, Z., et al. Factors that influence the cutaneous synthesis and dietary sources of vitamin D. Arch. Biochem. Biophys. 460(2), 213-217 (2007).

4. Xu, G., Salen, G., Shefer, S., et al. Reproducing abnormal cholesterol biosynthesis as seen in the Smith-Lemli-Opitz syndrome by inhibiting the conversion of 7-dehydrocholesterol to cholesterol in rats. J. Clin. Invest. 95(1), 76-81 (1995).

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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

String Representations

InChiKey (Click to copy)

UCTLRSWJYQTBFZ-DDPQNLDTSA-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/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1

SMILES (Click to copy)

C12=CC=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]