Structure Database (LMSD)

H HO H H O OH H H
Common Name
Cholesterol-5alpha-hydroperoxide
Systematic Name
3β-hydroxy-5α-cholest-6-ene-5-hydroperoxide
Synonyms
  • 5alpha-hydroperoxy-cholest-6-ene-3beta-ol
LM ID
LMST01010278
Formula
C27H46O3
Exact Mass
Calculate m/z
418.344695
Sum Composition
ST 27:1;O3
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

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

String Representations

InChiKey (Click to copy)
CUIXDAUTEMBARD-POBUXQGNSA-N
InChi (Click to copy)
InChI=1S/C27H46O3/c1-18(2)7-6-8-19(3)22-9-10-23-21-12-16-27(30-29)17-20(28)11-15-26(27,5)24(21)13-14-25(22,23)4/h12,16,18-24,28-29H,6-11,13-15,17H2,1-5H3/t19-,20+,21+,22-,23+,24+,25-,26-,27-/m1/s1
SMILES (Click to copy)
[C@]12(C=C[C@@]3(OO)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]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rattus norvegicus (#10116)
Mammalia (#40674)
Cholesterol oxidation in the retina: implications of 7KCh formation in chronic inflammation and age-related macular degeneration.,
J Lipid Res, 2010
Pubmed ID: 20567027

Other Databases

PubChem CID
14017141

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 449.95
Topological Polar Surface Area 49.69
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 7.60
Molar Refractivity 122.82

Admin

Created at
-
Updated at
27th May 2021