Zymosterone

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
CAS Number	27192-37-6  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:52386  N
KEGG	C22136  N
PubChem CID	22298942
InChI 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
SMILES C[C@]1(CC2)C(CCC3=C1CC[C@@]4(C)C3CCC4[C@@H](CCC=C(C)C)C)CC2=O
Properties
Chemical formula	C27H42O
Molar mass	382.632 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N (what is  YN ?) Infobox references

Zymosterone is a synthetic anabolic steroid that has been studied for its potential use in veterinary medicine and as a growth promoter in livestock. The compound is structurally related to testosterone and is known for its strong anabolic effects with relatively low androgenic activity. ^{[2] [3] [4]}

Uses

Zymosterone, NADPH and H(+) react to produce zymosterol and NADP(+). This reaction takes place in the endoplasmic reticulum, catalyzed by HSD17B7. ^[5]

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

References

1. "zymosterone | SGD". yeastgenome.org. Retrieved 20 July 2025.
2. "zymosterone". Sigma Aldrich . Retrieved 20 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 . Retrieved 20 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 . Retrieved 20 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. Retrieved 20 July 2025.
6. "Zymosterone | Dihydrofolate reductase (DHFR) | MedChemExpress". MedchemExpress.com. Retrieved 20 July 2025.