Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H44O |
| Molecular Weight | 384.6377 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC=C(C)C
InChI
InChIKey=AVSXSVCZWQODGV-DPAQBDIFSA-N
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/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
| Molecular Formula | C27H44O |
| Molecular Weight | 384.6377 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Desmosterol is an immediate precursor of cholesterol in the Bloch pathway of sterol synthesis and an abundant membrane lipid in specific cell types. Desmosterol has become of particular interest in the pathogenesis of Alzheimer's disease (AD) because of the report that the activity of the gene coding for the enzyme Δ24-dehydrocholesterol reductase (DHCR24), which metabolizes desmosterol to cholesterol, is selectively reduced in the affected areas of the brain. Any change in the pattern of C27 sterol intermediates in cholesterol synthesis merits investigation with respect to the pathogenesis of AD, since neurosteroids such as progesterone can modulate the tissue levels. The significant elevation of plasma desmosterol levels was revealed in patients with desmosterolosis, a rare disorder of cholesterol biosynthesis, which is caused by mutations in DHCR24. In addition, was shown, that desmosterol can be oxidized by Cytochrome P450 46A1, which is expressed in brain and as a consequence, the formation of that oxysterols in the brain could be related to the Smith-Lemli-Opitz syndrome, desmosterolosis, and other relevant diseases, as well as with signal transduction by lipids.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q15392 Gene ID: 1718.0 Gene Symbol: DHCR24 Target Organism: Homo sapiens (Human) |
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Target ID: Q9Y6A2 Gene ID: 10858.0 Gene Symbol: CYP46A1 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Diagnostic | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Substrate specificity of lecithin:cholesterol acyltransferase. Esterification of desmosterol, b-sitosterol, and cholecalciferol in human plasma. | 1975 Nov |
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| Precise quantitative determination of phytosterols, stanols, and cholesterol metabolites in human serum by capillary gas-liquid chromatography. | 1999 Sep 10 |
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| Comparative behavior of sterols in phosphatidylcholine-sterol monolayer films. | 2001 Apr 2 |
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| Apolipoprotein E phenotype regulates cholesterol absorption in healthy 13-month-old children--The STRIP Study. | 2001 Dec |
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| Quantitative analysis of desmosterol, cholesterol and cholesterol sulfate in semen by high-performance liquid chromatography. | 2001 Nov 23 |
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| Influence of simvastatin, pravastatin, and BM 15.766 on neutral sterols in liver and testis of guinea pigs. | 2002 Apr |
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| Short-term LDL cholesterol-lowering efficacy of plant stanol esters. | 2002 Aug 27 |
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| Effects of calcium and plant sterols on serum lipids in obese Zucker rats on a low-fat diet. | 2002 Mar |
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| Structural features of sterols required to inhibit human sperm capacitation. | 2003 Apr |
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| Decrease in order of human sperm lipids during capacitation. | 2003 Aug |
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| First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol. | 2003 Feb |
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| Identification of farnesoid X receptor beta as a novel mammalian nuclear receptor sensing lanosterol. | 2003 Feb |
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| Late gestational lung hypoplasia in a mouse model of the Smith-Lemli-Opitz syndrome. | 2004 Feb 2 |
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| Reactive oxygen species and sperm cells. | 2004 Mar 23 |
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| A comparison of the behavior of cholesterol and selected derivatives in mixed sterol-phospholipid Langmuir monolayers: a fluorescence microscopy study. | 2005 Jul |
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| Recent insights into the Smith-Lemli-Opitz syndrome. | 2005 Nov |
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| Regulation of hippocampal cholesterol metabolism by apoE and environmental stimulation. | 2005 Nov |
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| Reductions in cholesterol and synaptic markers in association cortex in mood disorders. | 2005 Oct |
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| Analysis of sterols by high-performance liquid chromatography/mass spectrometry combined with chemometrics. | 2006 |
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| Oxysterols suppress inducible nitric oxide synthase expression in lipopolysaccharide-stimulated astrocytes through liver X receptor. | 2006 Feb 6 |
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| Significance of sterol structural specificity. Desmosterol cannot replace cholesterol in lipid rafts. | 2006 Jan 6 |
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| Changes in serum level and metabolism of cholesterol with plant stanol esters in postmenopausal women with and without coronary artery disease. | 2006 Mar-Apr |
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| Serum adipokines are associated with cholesterol metabolism in the metabolic syndrome. | 2007 Aug |
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| Annexin A6-induced alterations in cholesterol transport and caveolin export from the Golgi complex. | 2007 Nov |
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| Atorvastatin in patients with primary biliary cirrhosis and incomplete biochemical response to ursodeoxycholic acid. | 2007 Sep |
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| The distribution of squalene and non-cholesterol sterols in lipoproteins in type 2 diabetes. | 2007 Sep |
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| Homology modelling of human DHCR24 (seladin-1) and analysis of its binding properties through molecular docking and dynamics simulations. | 2008 Aug |
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| Differential effects of cholesterol and its immediate biosynthetic precursors on membrane organization. | 2008 May 20 |
Sample Use Guides
Enzymatic assays with desmosterol were carried out in a 0.5 ml reaction volume containing 1.0 μM P450 46A1, 2.0 μM NADPH-P450 reductase, 100 mM potassium phosphate buffer (pH 7.5), 150 μM L-α-1,2-dilauroyl-sn-glycero-3-phosphocholine, and (unless indicated otherwise) a final substrate concentration of 15 μM. Incubation of desmosterol with P450 46A1 yielded two products: 24S,25-epoxycholesterol and 27-hydroxydesmosterol.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 07:59:48 GMT 2023
by
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on
Sat Dec 16 07:59:48 GMT 2023
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| Record UNII |
ANP93865R8
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| Record Status |
Validated (UNII)
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| Record Version |
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17737
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Desmosterol
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m4197
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