17alpha,20alpha-Dihydroxypregn-4-en-3-one (BioDeep_00000005548)

Main id: BioDeep_00000637522

 

human metabolite Endogenous


代谢物信息卡片


(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

化学式: C21H32O3 (332.2351)
中文名称: 4-孕烯-17α,20α-二醇-3-酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O)O
InChI: InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12-13,16-18,22,24H,4-11H2,1-3H3/t13-,16+,17-,18-,19-,20-,21-/m0/s1

描述信息

17 alpha,20alpha-Dihydroxypregn-4-en-3-one, also known as 17,20 alpha-OHP or 20alpha-dihydroxyprogesterone, is a steroid hormone that is elevated in late pregnancy. In particular, the concentration of plasma 17,20 alpha-OHP is significantly increased during the third trimester of pregnancy, and the increment continues to increase through labour and delivery (PMID:6874891). 17,20 alpha-OHP is known to be a substrate for the enzyme 20alpha-hydroxysteroid dehydrogenase or 20alpha-HSD (EC 1.1.1.149). This enzyme catalyzes the following chemical reaction: 17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+ = 17alpha-hydroxyprogesterone + NAD(P)H + H+. This enzyme is actively involved in the control of progesterone homeostasis in the pregnancy of mammals. While 20alpha-HSD expression and activity is downregulated in the corpus luteum of pregnancy, 24 hours prior to parturition, ovarian 20alpha-HSD activity is acutely stimulated. 17,20 alpha-OHP is a biologically weaker progestin. Progestin facilitates estrogen induction of the preovulatory luteinizing hormone (LH) surge. It is known that 17,20 alpha-OHP is increased at midcycle but its importance in regulating LH has not been studied. However, periovulatory levels of 17,20 alpha-OHP do not play a role in modulating the estrogen-induced bioactive LH surge (PMID:2245841).
17 alpha, 20 alpha-dihydroxy-4-pregnen-3-one (17 alpha, 20 alpha-OHP) is a steroid hormone that is elevated in late pregnancy. In particular, the concentration of plasma 17,20 alpha-OHP is significantly increased during the third trimester of pregnancy, and the increment continues to increase through labor and delivery (PMID: 6874891). 17 alpha, 20 alpha-dihydroxy-4-pregnen-3-one is known to be a substrate for the enzyme 20a-hydroxysteroid dehydrogenase or 20alpha-HSD (EC 1.1.1.149). This enzyme catalyzes the chemical reaction: 17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+ = 17alpha-hydroxyprogesterone + NAD(P)H + H+. This enzyme is actively involved in the control of progesterone homeostasis in pregnancy of mammals. While 20alpha-HSD expression and activity is downregulated in the corpus luteum of pregnancy, 24 hrs prior to parturition ovarian 20alpha-HSD activity is acutely stimulated. [HMDB]

同义名列表

40 个代谢物同义名

(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one; 17alpha-Hydroxy-20alpha-dihydroprogesterone; 17-alpha,20-alpha-Dihydroxypregn-4-en-3-one; 17alpha,20alpha-Dihydroxypregn-4-ene-3-one; 17alpha,20alpha-Dihydroxypregn-4-en-3-one; 17alpha,20alpha-Dihydroxy-4-pregnen-3-one; Pregn-4-ene-17alpha,20alpha-diol-3-one; 17alpha,20alpha-Dihydroxyprogesterone; (20S)-17,20-dihydroxypregn-4-en-3-one; 4-Pregnen-17alpha, 20alpha-diol-3-one; 17,20alpha-Dihydroxy-pregn-4-en-3-one; 17,20alpha-Dihydroxy-4-pregnen-3-one; 17-a,20-a-Dihydroxypregn-4-en-3-one; 17-α,20-α-dihydroxypregn-4-en-3-one; 17a-Hydroxy-20a-dihydroprogesterone; 17α-Hydroxy-20α-dihydroprogesterone; 17a,20a-Dihydroxypregn-4-ene-3-one; 17α,20α-Dihydroxypregn-4-ene-3-one; 17a,20a-Dihydroxy-4-pregnen-3-one; 17,20α-Dihydroxy-pregn-4-en-3-one; 17a,20a-Dihydroxypregn-4-en-3-one; 17,20a-Dihydroxy-pregn-4-en-3-one; 17Α,20α-dihydroxypregn-4-en-3-one; 17α,20α-Dihydroxy-4-pregnen-3-one; 17,20α-Dihydroxy-4-pregnen-3-one; 17,20a-Dihydroxy-4-pregnen-3-one; Pregn-4-ene-17α,20α-diol-3-one; Pregn-4-ene-17a,20a-diol-3-one; 17a,20a-Dihydroxyprogesterone; 4-Pregnen-17a, 20a-diol-3-one; 4-Pregnen-17α, 20α-diol-3-one; 17α,20α-Dihydroxyprogesterone; 20alpha-Dihydroxyprogesterone; 20-alfa-Dhydrodydrogesterone; 20α-Dihydroxyprogesterone; 20a-Dihydroxyprogesterone; 17 alpha, 20 alpha-OHP; 17 alpha, 20 alpha-P; 17,20 alpha-OHP; 17alpha,20alpha-Dihydroxypregn-4-en-3-one



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代谢反应

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1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

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文献列表

  • Sylvain Milla, Xavier Terrien, Armin Sturm, Fidaa Ibrahim, Franck Giton, Jean Fiet, Patrick Prunet, Florence Le Gac. Plasma 11-deoxycorticosterone (DOC) and mineralocorticoid receptor testicular expression during rainbow trout Oncorhynchus mykiss spermiation: implication with 17alpha, 20beta-dihydroxyprogesterone on the milt fluidity?. Reproductive biology and endocrinology : RB&E. 2008 May; 6(?):19. doi: 10.1186/1477-7827-6-19. [PMID: 18489781]