Structure Database (LMSD)

Common Name
6alpha-hydroxycholestanol
Systematic Name
cholestan-3β,6α-diol
Synonyms
LM ID
LMST01010135
Formula
C27H48O2
Exact Mass
Calculate m/z
404.365431
Sum Composition
ST 27:0;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Cholesterol and derivatives [ST0101]

Biological Context

6α-hydroxy Cholesterol is an oxysterol that increases superoxide anion production in SK-N-BE cells when used at concentrations of 50 and 100 μM.1

This information has been provided by Cayman Chemical

References

1. Zarrouk, A., Nury, T., Samadi, M., et al. Effects of cholesterol oxides on cell death induction and calcium increase in human neuronal cells (SK-N-BE) and evaluation of the protective effects of docosahexaenoic acid (DHA; C22:6 n-3). Steroids 99(Pt B), 238-247 (2015).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mus musculus (#10090)
Mammalia (#40674)
Subcellular organelle lipidomics in TLR-4-activated macrophages.,
J Lipid Res, 2010
Pubmed ID: 20574076

String Representations

InChiKey (Click to copy)
PMWTYEQRXYIMND-XNZKQLDXSA-N
InChi (Click to copy)
InChI=1S/C27H48O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-16-25(29)24-15-19(28)11-13-27(24,5)23(20)12-14-26(21,22)4/h17-25,28-29H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25+,26-,27-/m1/s1
SMILES (Click to copy)
[C@]12(C[C@H](O)[C@@]3([H])C[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]

Other Databases

CHEBI ID
132620
PubChem CID
6367315
Cayman ID
25715

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 4
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 443.80
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 7.01
Molar Refractivity 121.49

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Updated at
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