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Zymosterone

From Wikipedia, the free encyclopedia
Zymosterone
Names
IUPAC name
(5S,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,4,5,6,7,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Other names
cholesta-8(9),24-dien-3-one; zymosterol intermediate 2[1]
Identifiers
3D model (JSmol)
ChEBI
KEGG
  • InChI=1S/C27H42O/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/h7,19-20,23-24H,6,8-17H2,1-5H3/t19-,20?,23?,24?,26+,27-/m1/s1 ☒N
    Key: AUNLIRXIJAVBNM-ZSFXRWSJSA-N ☒N
  • C[C@]1(CC2)C(CCC3=C1CC[C@@]4(C)C3CCC4[C@@H](CCC=C(C)C)C)CC2=O
Properties
C27H42O
Molar mass382.632 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N (what is checkY☒N ?)
Chemical compound

Zymosterone is a syntheticanabolic steroid that has been studied for its potential use in veterinary medicine and as agrowth promoter in livestock. The compound is structurally related totestosterone and is known for its strong anabolic effects with relatively low androgenic activity.[2][3][4]

Uses

[edit]

Zymosterone,NADPH and H(+) react to producezymosterol and NADP(+). This reaction takes place in theendoplasmic reticulum, catalyzed byHSD17B7.[5]

The conversion of zymosterone to zymosterol plays an important role in the synthesis ofergosterol, a crucial component for maintaining the structure and functionality of fungalcell membranes. Similar to how cholesterol functions in animal cells, ergosterol supports the membrane's stability and participates in multiple cellular activities.[6]

References

[edit]
  1. ^"zymosterone | SGD". yeastgenome.org. Retrieved20 July 2025.
  2. ^"zymosterone".Sigma Aldrich. Retrieved20 July 2025.
  3. ^Hitzler, Pascal; Fernández, Miriam; Janowicz, Krzysztof; Zaveri, Amrapali; Gray, Alasdair J. G.; Lopez, Vanessa; Haller, Armin; Hammar, Karl (24 May 2019).The Semantic Web: 16th International Conference, ESWC 2019, Portorož, Slovenia, June 2–6, 2019, Proceedings.Springer. p. 151.ISBN 978-3-030-21348-0. Retrieved20 July 2025.
  4. ^Hill, R. A.; Makin, H. L. J.; Kirk, D. N.; Murphy, G. M. (23 May 1991).Dictionary of Steroids.CRC Press. p. 110.ISBN 978-0-412-27060-4. Retrieved20 July 2025.
  5. ^"Reactome | Zymosterone (cholesta-8(9),24-dien-3-one) is reduced to zymosterol (cholesta-8(9),24-dien-3beta-ol)". reactome.org. Retrieved20 July 2025.
  6. ^"Zymosterone | Dihydrofolate reductase (DHFR) | MedChemExpress". MedchemExpress.com. Retrieved20 July 2025.
Mevalonate pathway
toHMG-CoA
Ketone bodies
toDMAPP
Geranyl-
Carotenoid
Non-mevalonate pathway
ToCholesterol
FromCholesterol
toSteroid hormones
Nonhuman
ToSitosterol
ToErgocalciferol
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