Structure Database (LMSD)

Common Name
19-hydroxycholesterol
Systematic Name
Cholest-5-en-3β,19-diol
Synonyms
LM ID
LMST01010274
Formula
C27H46O2
Exact Mass
Calculate m/z
402.349781
Sum Composition
ST 27:1;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

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

Biological Context

19-hydroxy Cholesterol is formed during metabolic oxidation of cholesterol. It has been used as an internal standard for the quantitative determination of sterols by mass spectroscopic analysis.1

This information has been provided by Cayman Chemical

References

1. Yamaga, N., Ogura, Y., Islam, A., et al. Utility of 19-hydroxycholesterol as an internal standard compound for the quantitative determination of sterols using capillary gas chromatograph. Yonago Acta medica 45, 27-33 (2002).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
The effects of cholesterol oxidation products in sickle and normal red blood cell membranes.,
Biochim Biophys Acta, 1992
Pubmed ID: 1543714

String Representations

InChiKey (Click to copy)
YRWIUNJQYGATHV-FTLVODPJSA-N
InChi (Click to copy)
InChI=1S/C27H46O2/c1-18(2)6-5-7-19(3)23-10-11-24-22-9-8-20-16-21(29)12-15-27(20,17-28)25(22)13-14-26(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t19-,21+,22+,23-,24+,25+,26-,27-/m1/s1
SMILES (Click to copy)
C1[C@]2(CO)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCCC(C)C)CC[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1

Other Databases

CHEBI ID
166800
PubChem CID
6453303
Cayman ID
15209

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 441.16
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 6.93
Molar Refractivity 121.47

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Created at
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Updated at
7th Apr 2025