Structure Database (LMSD)

H O H H H H
Common Name
3-ketocholesterol
Systematic Name
Cholest-5-en-3-one
Synonyms
  • Cholestenone (delta 5)
LM ID
LMST01010248
Formula
C27H44O
Exact Mass
Calculate m/z
384.339215
Sum Composition
ST 27:2;O
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)
GGCLNOIGPMGLDB-GYKMGIIDSA-N
InChi (Click to copy)
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,22-25H,6-8,10-17H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1
SMILES (Click to copy)
[C@]12(CC=C3CC(=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

Reference
Kieslich, K., et al. J. Basic. Microbiol., 25, 461 (1985)
Wakeham, S., et al.: Nature, 342, 787 (1989)
Pollegioni, L., et al.: Eur. J. Biochem., 264, 140 (1999)
Kniemeyer, O., et al.: J. Biol. Chem., 276, 21381 (2001)

Other Databases

CHEBI ID
63906
PubChem CID
9908107
SwissLipids ID
SLM:000000288

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 4
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 429.73
Topological Polar Surface Area 17.07
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 1
logP 7.60
Molar Refractivity 118.05

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Updated at
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