LIPID MAPS

Structure Database (LMSD)

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Common Name

20S-hydroxycholesterol

Systematic Name

cholest-5-en-3β,20S-diol

Synonyms

(20S)-20-Hydroxycholesterol
20beta-Hydroxycholesterol
20(S)-OHC

LM ID

LMST01010201

Formula

C₂₇H₄₆O₂

Exact Mass

Calculate m/z

402.34978

Sum Composition

ST 27:1;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

20(S)-hydroxy Cholesterol is an allosteric agonist of the smoothened (Smo) receptor that activates the hedgehog (Hh) signaling pathway with an EC50 value of approxiately 3 μM in a gene transcription reporter assay using NIH3T3 cells.¹ 20(S)-hydroxy Cholesterol is necessary for normal Hh signaling. It induces Smo accumulation in primary cilia, an early event in signaling, and binds to the extracellular, cysteine-rich domain of Smo.^1,2 20(S)-hydroxy Cholesterol also stimulates osteogenic differentiation of pluripotent bone marrow stromal cells, a process mediated via Hh and Notch signaling.^3,4,5

This information has been provided by Cayman Chemical

References

1. Dwyer, J.R., Sever, N., Carlson, M., et al. Oxysterols are novel activators of the hedgehog signaling pathway in pluripotent mesenchymal cells. J. Biol. Chem. 282(12), 8959-8968 (2007).

2. Nachtergaele, S., Mydock, L.K., Krishnan, K., et al. Oxysterols are allosteric activators of the oncoprotein Smoothened. Nat. Chem. Biol. 8(2), 211-220 (2012).

3. Kha, H.T., Basseri, B., Shouhed, D., et al. Oxysterols regulate differentiation of mesenchymal stem cells: Pro-bone and anti-fat. J. Bone Miner. Metab. 19(5), 830-840 (2004).

4. Kim, W.-K., Meliton, V., Tetradis, S., et al. Osteogenic oxysterol, 20(S)-hydroxycholesterol, induces notch target gene expression in bone marrow stromal cells. J. Bone Miner. Metab. 25(4), 782-795 (2010).

5. Nedelcu, D., Liu, J., Xu, Y., et al. Oxysterol binding to the extracellular domain of smoothened in hedgehog signaling. Nat. Chem. Biol. 9(9), 557-564 (2013).

String Representations

InChiKey (Click to copy)

MCKLJFJEQRYRQT-APGJSSKUSA-N

InChi (Click to copy)

InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27-/m0/s1

SMILES (Click to copy)

C1C[C@H](O)CC2=CC[C@]3([H])[C@@]([H])([C@]21C)CC[C@]1(C)[C@@]([H])([C@@](O)(CCCC(C)C)C)CC[C@]13[H]