Structure Database (LMSD)

HO H O H H H H
Common Name
24-oxocholesterol
Systematic Name
24-oxo-cholest-5-en-3β-ol
Synonyms
  • 24-ketocholesterol
LM ID
LMST01010133
Formula
C27H44O2
Exact Mass
Calculate m/z
400.33413
Sum Composition
ST 27:2;O2
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)
PGLNLCWHYQYRGQ-ZHHJOTBYSA-N
InChi (Click to copy)
InChI=1S/C27H44O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-24,28H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
SMILES (Click to copy)
[C@@]12([H])CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCC(=O)C(C)C)CC[C@@]21[H]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Pelvetia canaliculata (#74467)
Phaeophyceae (#2870)
Isolation of 24-oxocholesterol from the marine brown alga Pelvetia canaliculata (Phaeophyceae).,
Acta Chem Scand, 1970
Pubmed ID: 5487826
Mus musculus (#10090)
Mammalia (#40674)
Targeted lipidomic analysis of oxysterols in the embryonic central nervous system.,
Mol Biosyst, 2009
Pubmed ID: 19381367
Hippospongia (#119430)
Demospongiae (#6042)
Marine Sterols,
Nat Prod Rep, 1991

Other Databases

CHEBI ID
172974
PubChem CID
11036808

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 4
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 438.52
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 6.85
Molar Refractivity 119.95

Admin

Created at
-
Updated at
30th Jul 2021