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Desmosterol information


Desmosterol
Skeletal formula of desmosterol
Ball-and-stick model of the desmosterol molecule
Names
IUPAC name
Cholesta-5,24-dien-3β-ol
Systematic IUPAC name
(1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-Dimethyl-1-[(2R)-6-methylhept-5-en-2-yl]-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
Identifiers
CAS Number
  • 313-04-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17737 checkY
ChEMBL
  • ChEMBL455876 checkY
ChemSpider
  • 388662 checkY
ECHA InfoCard 100.005.671 Edit this at Wikidata
IUPHAR/BPS
  • 2748
PubChem CID
  • 439577
UNII
  • ANP93865R8 checkY
CompTox Dashboard (EPA)
  • DTXSID10878676 Edit this at Wikidata
InChI
  • 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 checkY
    Key: AVSXSVCZWQODGV-DPAQBDIFSA-N checkY
  • InChI=1/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
    Key: AVSXSVCZWQODGV-DPAQBDIFBV
SMILES
  • O[C@@H]4C/C3=C/C[C@@H]1[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CC\C=C(/C)C)C)[C@@]3(C)CC4
Properties
Chemical formula
 C27H44O
Molar mass 384.64 g/mol
Appearance White powder
Melting point 121.5 °C (250.7 °F; 394.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Desmosterol (Cholesta-5,24-dien-3β-ol) is a lipid present in the membrane of phytoplankton and an intermediate product in cholesterol synthesis in mammal cells.[1] Structurally, desmosterol has a similar backbone to cholesterol, with the exception of an additional double bond in the structure of desmosterol.

The similarity can be seen biologically through the synthesis of cholesterol in the human body, as desmosterol is the immediate precursor to cholesterol in the Bloch pathway.[2] Desmosterol is accumulated in desmosterolosis and undergoes reduction with the catalyst 24-dehydrocholesterol reductase to form cholesterol.[3]

In 2014, desmosterol was named the Molecule of the Year 2012 by the International Society for Molecular and Cell Biology and Biotechnology Protocols and Researches (ISMCBBPR).[4]

Structure of cholesterol and its immediate precursor, desmosterol.
  1. ^ Kamal, Md. Arif; Pal, Antara (September 2023). "Effect of Desmosterol, Lathosterol and Coprostanol on the phase behaviour of phospholipid membranes". Colloids and Surfaces A: Physicochemical and Engineering Aspects. 673: 131489. doi:10.1016/j.colsurfa.2023.131489.
  2. ^ Bloch, Konrad (October 1965). "The Biological Synthesis of Cholesterol". Science. 150 (3692): 19–28. Bibcode:1965Sci...150...19B. doi:10.1126/science.150.3692.19. PMID 5319508.
  3. ^ Keber, Rok; Rozman, Damjana; Horvat, Simon (January 2013). "Sterols in spermatogenesis and sperm maturation". Journal of Lipid Research. 54 (1): 20–33. doi:10.1194/jlr.R032326. PMC 3520525. PMID 23093550.
  4. ^ "Announcing ISMCBBPR's Molecule of the Year 2012". Archived from the original on 2015-09-24. Retrieved 2014-02-22.

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24-dehydrocholesterol reductase (24-DHCR), preventing the formation of cholesterol from desmosterol. Although it primarily acts to inhibit 24-DHCR, the drug also inhibits...

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mass: 384.339216 u) may refer to: Cholecalciferol 7-Dehydrocholesterol Desmosterol Previtamin D3 Zymosterol, a cholesterol intermediate This set index page...

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ABCG4

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determined. ABCG4 has demonstrated, in vitro, to participate in the efflux of desmosterol and amyloid-β peptide (Aβ). It is highly expressed in the brain, but...

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president, Isidro A. T. Savillo, announces the Molecule of the Year 2012 as Desmosterol. 24 February Following a long delay due to technical issues, the first...

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