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 |
|---|---|---|
| Interannual variations in the lipids of the Antarctic pteropods Clione limacina and Clio pyramidata. | 2001 Mar |
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| Acute effects of weight reduction on cholesterol metabolism in obese type 2 diabetes. | 2002 Feb |
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| Heritability of plasma noncholesterol sterols and relationship to DNA sequence polymorphism in ABCG5 and ABCG8. | 2002 Mar |
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| Structural features of sterols required to inhibit human sperm capacitation. | 2003 Apr |
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| Impact of simvastatin, niacin, and/or antioxidants on cholesterol metabolism in CAD patients with low HDL. | 2003 Apr |
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| Serum cholesterol, precursors and metabolites and cognitive performance in an aging population. | 2003 Jan-Feb |
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| Synthesis and absorption markers of cholesterol in serum and lipoproteins during a large dose of statin treatment. | 2003 Nov |
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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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| Insulin resistance is associated with increased cholesterol synthesis and decreased cholesterol absorption in normoglycemic men. | 2004 Mar |
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| Secretion of sterols and the NPC2 protein from primary astrocytes. | 2004 Nov 19 |
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| Sperm membrane fatty acid composition in the Eastern grey kangaroo (Macropus giganteus), koala (Phascolarctos cinereus), and common wombat (Vombatus ursinus) and its relationship to cold shock injury and cryopreservation success. | 2004 Oct |
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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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| Desmosterol may replace cholesterol in lipid membranes. | 2005 Mar |
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| Postprandial behavior of plasma squalene and non-cholesterol sterols in men with varying cholesterol absorption. | 2006 Dec |
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| Studies on the transcriptional regulation of cholesterol 24-hydroxylase (CYP46A1): marked insensitivity toward different regulatory axes. | 2006 Feb 17 |
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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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| Simultaneous determination of plasmatic phytosterols and cholesterol precursors using gas chromatography-mass spectrometry (GC-MS) with selective ion monitoring (SIM). | 2006 Sep 14 |
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| Sterol intermediates from cholesterol biosynthetic pathway as liver X receptor ligands. | 2006 Sep 22 |
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| Studies on the cholesterol-free mouse: strong activation of LXR-regulated hepatic genes when replacing cholesterol with desmosterol. | 2007 Oct |
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| ATP-binding cassette transporters G1 and G4 mediate cholesterol and desmosterol efflux to HDL and regulate sterol accumulation in the brain. | 2008 Apr |
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
admin
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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