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
C[C@H](CCC=C(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
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) |
|||
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 |
|---|---|---|
| Homology modelling of human DHCR24 (seladin-1) and analysis of its binding properties through molecular docking and dynamics simulations. | 2008-08 |
|
| Cholesterol substitution increases the structural heterogeneity of caveolae. | 2008-05-23 |
|
| Differential effects of cholesterol and its immediate biosynthetic precursors on membrane organization. | 2008-05-20 |
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| SREBP-1c gene polymorphism is associated with increased inhibition of cholesterol-absorption in response to ezetimibe treatment. | 2008-05 |
|
| Increased expression of aquaporin-3 in the epidermis of DHCR24 knockout mice. | 2008-04 |
|
| ATP-binding cassette transporters G1 and G4 mediate cholesterol and desmosterol efflux to HDL and regulate sterol accumulation in the brain. | 2008-04 |
|
| Mutational screening analysis of DHCR24/seladin-1 gene in Italian familial Alzheimer's disease. | 2008-01-05 |
|
| Effects of ezetimibe, simvastatin, atorvastatin, and ezetimibe-statin therapies on non-cholesterol sterols in patients with primary hypercholesterolemia. | 2008-01 |
|
| Moderately elevated plant sterol levels are associated with reduced cardiovascular risk--the LASA study. | 2008-01 |
|
| Annexin A6-induced alterations in cholesterol transport and caveolin export from the Golgi complex. | 2007-11 |
|
| Studies on the cholesterol-free mouse: strong activation of LXR-regulated hepatic genes when replacing cholesterol with desmosterol. | 2007-10 |
|
| Quantifying raft proteins in neonatal mouse brain by 'tube-gel' protein digestion label-free shotgun proteomics. | 2007-09-24 |
|
| Atorvastatin in patients with primary biliary cirrhosis and incomplete biochemical response to ursodeoxycholic acid. | 2007-09 |
|
| The distribution of squalene and non-cholesterol sterols in lipoproteins in type 2 diabetes. | 2007-09 |
|
| Serum adipokines are associated with cholesterol metabolism in the metabolic syndrome. | 2007-08 |
|
| Role of sterol type on lateral pressure profiles of lipid membranes affecting membrane protein functionality: Comparison between cholesterol, desmosterol, 7-dehydrocholesterol and ketosterol. | 2007-08 |
|
| Seasonal and geographical variations of sterol composition in snow crab hepatopancreas and pelagic fish viscera from Eastern Quebec. | 2007-07 |
|
| Loss of apolipoprotein E exacerbates the neonatal lethality of the Smith-Lemli-Opitz syndrome mouse. | 2007-05 |
|
| Separation and determination of diversiform phytosterols in food materials using supercritical carbon dioxide extraction and ultraperformance liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry. | 2007-04-04 |
|
| Assessing the nature of lipid raft membranes. | 2007-02-23 |
|
| [Factors modulating parameters of cholesterol homeostasis in the metabolic syndrome]. | 2007 |
|
| Postprandial behavior of plasma squalene and non-cholesterol sterols in men with varying cholesterol absorption. | 2006-12 |
|
| Endothelial function in hypercholesterolemic subjects: Effects of plant stanol and sterol esters. | 2006-10 |
|
| Sterol intermediates from cholesterol biosynthetic pathway as liver X receptor ligands. | 2006-09-22 |
|
| Simultaneous determination of plasmatic phytosterols and cholesterol precursors using gas chromatography-mass spectrometry (GC-MS) with selective ion monitoring (SIM). | 2006-09-14 |
|
| Cholesterol precursors stabilize ordinary and ceramide-rich ordered lipid domains (lipid rafts) to different degrees. Implications for the Bloch hypothesis and sterol biosynthesis disorders. | 2006-08-04 |
|
| Neuronal differentiation of human mesenchymal stem cells: changes in the expression of the Alzheimer's disease-related gene seladin-1. | 2006-08-01 |
|
| Regulation of cholesterol 25-hydroxylase expression by vitamin D3 metabolites in human prostate stromal cells. | 2006-06-30 |
|
| HPLC method for quantification and characterization of cholesterol and its oxidation products in eggs. | 2006-06 |
|
| DHCR24-knockout embryonic fibroblasts are susceptible to serum withdrawal-induced apoptosis because of dysfunction of caveolae and insulin-Akt-Bad signaling. | 2006-06 |
|
| Phase behavior of lipid monolayers containing DPPC and cholesterol analogs. | 2006-05-01 |
|
| Changes in serum level and metabolism of cholesterol with plant stanol esters in postmenopausal women with and without coronary artery disease. | 2006-04-29 |
|
| DHCR24 gene knockout mice demonstrate lethal dermopathy with differentiation and maturation defects in the epidermis. | 2006-03 |
|
| Studies on the transcriptional regulation of cholesterol 24-hydroxylase (CYP46A1): marked insensitivity toward different regulatory axes. | 2006-02-17 |
|
| Cholesterol absorption and synthesis in pediatric kidney, liver, and heart transplant recipients. | 2006-02-15 |
|
| Oxysterols suppress inducible nitric oxide synthase expression in lipopolysaccharide-stimulated astrocytes through liver X receptor. | 2006-02-06 |
|
| Serum noncholesterol sterols in children with heterozygous familial hypercholesterolemia undergoing pravastatin therapy. | 2006-02 |
|
| Significance of sterol structural specificity. Desmosterol cannot replace cholesterol in lipid rafts. | 2006-01-06 |
|
| Analysis of sterols by high-performance liquid chromatography/mass spectrometry combined with chemometrics. | 2006 |
|
| Sterol profiling of amniotic fluid: a routine method for the detection of distal cholesterol synthesis deficit. | 2005-11 |
|
| Recent insights into the Smith-Lemli-Opitz syndrome. | 2005-11 |
|
| Regulation of hippocampal cholesterol metabolism by apoE and environmental stimulation. | 2005-11 |
|
| Reductions in cholesterol and synaptic markers in association cortex in mood disorders. | 2005-10 |
|
| Diffusion of cholesterol and its precursors in lipid membranes studied by 1H pulsed field gradient magic angle spinning NMR. | 2005-10 |
|
| Comparative aspects of sperm membrane fatty acid composition in silver (Vulpes vulpes) and blue (Alopex lagopus) foxes, and their relationship to cell cryopreservation. | 2005-08 |
|
| A comparison of the behavior of cholesterol and selected derivatives in mixed sterol-phospholipid Langmuir monolayers: a fluorescence microscopy study. | 2005-07 |
|
| Cytochrome P450 17alpha hydroxylase/17,20 lyase (CYP17) function in cholesterol biosynthesis: identification of squalene monooxygenase (epoxidase) activity associated with CYP17 in Leydig cells. | 2005-07 |
|
| Lipid composition of deep-sea hydrothermal vent tubeworm Riftia pachyptila, crabs Munidopsis subsquamosa and Bythograea thermydron, mussels Bathymodiolus sp. and limpets Lepetodrilus spp. | 2005-06 |
|
| Determination of sterols in biological samples by SPME with on-fiber derivatization and GC/FID. | 2005-04 |
|
| Substrate specificity of lecithin:cholesterol acyltransferase. Esterification of desmosterol, b-sitosterol, and cholecalciferol in human plasma. | 1975-11 |
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
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admin
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Edited
Mon Mar 31 21:48:41 GMT 2025
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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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75739-3
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Desmosterol
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| Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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