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Structure Database (LMSD)

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Common Name

5alpha,6beta-dihydroxycholestanol

Systematic Name

cholestane-3β,5α,6β-triol

Synonyms

LM ID

LMST01010052

Formula

C₂₇H₄₈O₃

Exact Mass

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420.360346

Sum Composition

ST 27:0;O3

Status

Curated

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Classification

Biological Context

5α,6β-Dihydroxycholestanol is an oxysterol metabolite of cholesterol formed from conversion of cholesterol epoxides by 5,6-epoxysterol hydrolase.^1,2 It inhibits NMDA-mediated calcium influx in HEK293 cells expressing NR1/NR2B NMDA receptors in a concentration-dependent manner. It also binds to voltage-gated sodium (Nav) channels and decreases action potentials in hippocampal neurons in vitro when used at a concentration of 10 µM.² It increases survival of spinal cord motoneurons, cortical neurons, and cerebellar granule neurons in vitro when used at concentrations ranging from 5 to 15 µM.³ 5α,6β-Dihydroxycholestanol is neuroprotective in a rat model of cerebral ischemia when administered at a dose of 12 mg/kg and increases latency to seizure onset and reduces severity of seizures induced by pentylenetetrazole (PTZ) in rats. 5α,6β-Dihydroxycholestanol has been used as a replacement for cholesterol in the study of cholesterol binding proteins.⁴

This information has been provided by Cayman Chemical

References

1. Aringer, L., and Eneroth, P. Formation and metabolism in vitro of 5,6-epoxides of cholesterol and β-sitosterol. J. Lipid Res. 15(4), 389-398 (1974).

2. Tang, L., Yan, M., Leng, T., et al. Cholestane-3β, 5α, 6β-triol suppresses neuronal hyperexcitability via binding to voltage-gated sodium channels. Biochem. Biophys. Res. Commun. 496(1), 95-100 (2018).

3. Hu, H., Zhou, Y., Leng, T., et al. The major cholesterol metabolite cholestane-3β,5α,6β-triol functions as an endogenous neuroprotectant. J. Neurosci. 34(34), 11426-11438 (2014).

4. Sheng, R., Kim, H., Lee, H., et al. Cholesterol selectively activates canonical Wnt signalling over non-canonical Wnt signalling. Nat. Commun. 5:4393, (2014).

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rattus norvegicus (#10116)

Mammalia (#40674)

Formation and metabolism in vitro of 5,6-epoxides of cholesterol and beta-sitosterol.,
J Lipid Res, 1974

Pubmed ID: 4152888

String Representations

InChiKey (Click to copy)

YMMFNKXZULYSOQ-RUXQDQFYSA-N

InChi (Click to copy)

InChI=1S/C27H48O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28-30H,6-16H2,1-5H3/t18-,19+,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])C[C@@H](O)[C@@]2(O)C[C@@H](O)C1