Desmosterol

Desmosterol
Names


IUPAC name (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Other names Cholesta-5,24-dien-3β-ol
Identifiers
CAS Number	313-04-2^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17737^Y
ChEMBL	ChEMBL455876^Y
ChemSpider	388662^Y
ECHA InfoCard	100.005.671
IUPHAR/BPS	2748
PubChem	439577
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^Y Key: AVSXSVCZWQODGV-DPAQBDIFSA-N^Y 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).
Y verify (what is ^YN ?)
Infobox references

Desmosterol is a molecule similar to cholesterol. Desmosterol is the immediate precursor of cholesterol in the Bloch pathway of cholesterol biosynthesis.^[1] 24-dehydrocholesterol reductase catalyses the reduction of desmosterol to cholesterol.^[2] It is accumulated in desmosterolosis.

In 2014, it was named the Molecule of the Year 2012 by the International Society for Molecular and Cell Biology and Biotechnology Protocols and Researches (ISMCBBPR).^[3]

References

↑ Vainio, S.; Jansen, M.; Koivusalo, M.; Rog, T.; Karttunen, M.; Vattulainen, I.; Ikonen, E. (25 October 2005). "Significance of Sterol Structural Specificity: DESMOSTEROL CANNOT REPLACE CHOLESTEROL IN LIPID RAFTS". Journal of Biological Chemistry. 281 (1): 348–355. doi:10.1074/jbc.M509530200. PMID 16249181. Retrieved 30 June 2015.
↑ Keber, R.; Rozman, D.; Horvat, S. (23 October 2012). "Sterols in spermatogenesis and sperm maturation". The Journal of Lipid Research. 54 (1): 20–33. doi:10.1194/jlr.R032326. PMID 23093550. Retrieved 30 June 2015.
↑ Announcing ISMCBBPR's Molecule of the Year 2012

Cholesterol and steroid metabolic intermediates

Mevalonate pathway

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA

Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid

to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate

Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate

Carotenoid	Prephytoene diphosphate Phytoene

Non-mevalonate pathway

To Cholesterol

From Cholesterol
(to steroids)

Steroid hormones

See here instead.

Nonhuman

Phytosterols	Stigmasterol Brassicasterol

Ergosterols	Ergosterol Ergocalciferol

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Desmosterol

See also

References