1662-06-2
Chemical Structure
17α,20β-Dihydroxy-4-pregnen-3-one
Synonym(s): 17,20β-P; 17,20β-DHP
- CAS No.: 1662-06-2
- Formula:C21H32O3
- Molecular Weight:332.48
IUPAC Name: (5s,8s)-3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one
InChIKey: MASCESDECGBIBB-FSHQYNQFSA-N
SMILES: C[C@@]12[C@](CC[C@]2(O)[C@H](O)C)([H])[C@@]3([H])[C@@](CC1)([H])[C@@]4(C(CC3)=CC(CC4)=O)C
Biological Activity: 17α,20β-Dihydroxy-4-pregnen-3-one (17,20β-P; 17,20β-DHP) acts as the maturation-inducing hormone (MIH) in salmonid fish and rainbow trout. 17α,20β-Dihydroxy-4-pregnen-3-one binds to oocyte-specific plasma membrane receptors and pertussis toxin-sensitive inhibitory G proteins in fish, inhibits Adenylate Cyclase and reduces intracellular cAMP via the membrane receptor-G protein coupling pathway, thereby initiating downstream signal transduction. 17α,20β-Dihydroxy-4-pregnen-3-one induces de novo synthesis of cyclin B, mediates the translation of cyclin B mRNA and the phosphorylation of cdc2, and promotes the production of maturation-promoting factor (MPF). 17α,20β-Dihydroxy-4-pregnen-3-one drives meiotic maturation of fish oocytes. 17α,20β-Dihydroxy-4-pregnen-3-one is applicable for development-related research[1][2].
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17α,20β-Dihydroxy-4-pregnen-3-one | 96.69% | 17α,20β-Dihydroxy-4-pregnen-3-one (17,20β-P; 17,20β-DHP) acts as the maturation-inducing hormone (MIH) in salmonid fish and rainbow trout. 17α,20β-Dihydroxy-4-pregnen-3-one binds to oocyte-specific plasma membrane receptors and pertussis toxin-sensitive inhibitory G proteins in fish, inhibits Adenylate Cyclase and reduces intracellular cAMP via the membrane receptor-G protein coupling pathway, thereby initiating downstream signal transduction. 17α,20β-Dihydroxy-4-pregnen-3-one induces de novo synthesis of cyclin B, mediates the translation of cyclin B mRNA and the phosphorylation of cdc2, and promotes the production of maturation-promoting factor (MPF). 17α,20β-Dihydroxy-4-pregnen-3-one drives meiotic maturation of fish oocytes. 17α,20β-Dihydroxy-4-pregnen-3-one is applicable for development-related research. | ||||||||||||||||||||
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- [1]. Nagahama Y, et al. 17 alpha,20 beta-dihydroxy-4-pregnen-3-one, a maturation-inducing hormone in fish oocytes: mechanisms of synthesis and action. Steroids. 1997 Jan;62(1):190-6. [Content Brief]
- [2]. Yoshikuni M, et al. Involvement of an inhibitory G-protein in the signal transduction pathway of maturation-inducing hormone (17 alpha,20 beta-dihydroxy-4-pregnen-3-one) action in rainbow trout (Oncorhynchus mykiss) oocytes. Developmental biology. 1994 Dec;166(2):615-22. [Content Brief]
Keywords
