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Structure Database (LMSD)

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Common Name

8-Dehydrocholesterol

Systematic Name

cholesta-5,8-dien-3β-ol

Synonyms

8-DHC

LM ID

LMST01010242

Formula

C₂₇H₄₄O

Exact Mass

Calculate m/z

384.339216

Sum Composition

ST 27:2;O

Status

Curated

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Classification

Biological Context

8-dehydro Cholesterol (8-DHC) is an isomer of the cholesterol precursor 7-DHC .^1,2,3 It accumulates in tissues and plasma in patients with Smith-Lemli-Opitz syndrome (SLOS), a disorder characterized by a mutation in DHCR7, the gene encoding 3β-hydroxysterol-Δ7-reductase, and decreased cholesterol levels in bodily tissues and fluids, as well as microcephaly, intellectual disability, and distinctive dysmorphic features. 8-DHC levels are increased in serum in a rat model of SLOS induced by the DHCR7 inhibitor AY 9944 .¹

This information has been provided by Cayman Chemical

References

1. Griffiths, W.J., Abdel-Khalik, J., Crick, P.J., et al. Sterols and oxysterols in plasma from Smith-Lemli-Opitz syndrome patients. J. Steroid Biochem. Mol. Biol. 169, 77-87 (2017).

2. Wolf, C., Chevy, F., Pham, J., et al. Changes in serum sterols of rats treated with 7-dehydrocholesterol-Δ7-reductase inhibitors: Comparison to levels in humans with Smith-Lemli-Opitz syndrome. J. Lipid. Res. 37(6), 1325-1333 (1996).

3. Björkhem, I., Starck, L., Andersson, U., et al. Oxysterols in the circulation of patients with the Smith-Lemli-Opitz syndrome: Abnormal levels of 24S- and 27-hydroxycholesterol. J. Lipid Res. 42(3), 366-371 (2001).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Identification of 8-dehydrocholesterol (cholesta-5,8-dien-3 beta-ol) in patients with Smith-Lemli-Opitz syndrome.,
J Lipid Res, 1995

Pubmed ID: 7616117

String Representations

InChiKey (Click to copy)

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

SMILES (Click to copy)

C12CC=C3C[C@@H](O)CC[C@]3(C)C=1CC[C@]1(C)[C@@]([H])([C@]([H])(C)CCCC(C)C)CC[C@@]21[H]