17alpha,20alpha-Dihydroxypregn-4-en-3-one (BioCAD00000002073)

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Metabolite Card

Formula: C21H32O3 (332.2351)
SMILES: [H][C@@]12CC[C@](O)([C@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

Synonyms [en]

(20S)-17,20-dihydroxypregn-4-en-3-one; 17alpha,20alpha-Dihydroxypregn-4-en-3-one; 17Α,20α-dihydroxypregn-4-en-3-one; 17 alpha, 20 alpha-OHP; 4-Pregnen-17alpha, 20alpha-diol-3-one; 4-Pregnen-17a, 20a-diol-3-one

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

17alpha,20alpha-Dihydroxypregn-4-en-3-one. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000002073). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 652-69-7
  • PubChem: 440368
  • ChEBI: ChEBI:16418
  • HMDB: HMDB0011653
  • LipidMaps: LMST02030183
  • KEGG: C04518
  • BioCyc: 17-ALPHA20-ALPHA-DIHYDROXYPREGN-4-EN-3-
  • Metlin: METLIN_57873

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R03325 1.1.1.149 17alpha,20alpha-dihydroxypregn-4-en-3-one:NADP+ 20-oxidoreductase
Rhea:RHEA:15854 1.1.1.149 (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NAD+ => 17α-hydroxyprogesterone + NADH + H+
Rhea:RHEA:15855 1.1.1.149 17α-hydroxyprogesterone + NADH + H+ => (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NAD+
Rhea:RHEA:15856 1.1.1.149 (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NAD+ <=> 17α-hydroxyprogesterone + NADH + H+
Rhea:RHEA:15858 1.1.1.149 (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NADP+ => 17α-hydroxyprogesterone + NADPH + H+
Rhea:RHEA:15859 1.1.1.149 17α-hydroxyprogesterone + NADPH + H+ => (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NADP+
Rhea:RHEA:15860 1.1.1.149 (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NADP+ <=> 17α-hydroxyprogesterone + NADPH + H+
BioCyc:1.1.1.149-RXN 1.1.1.149 17-ALPHA20-ALPHA-DIHYDROXYPREGN-4-EN-3- + NAD-P-OR-NOP<=>17-ALPHA-HYDROXYPROGESTERONE + NADH-P-OR-NOP + PROTON
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Organism Source

Taxonomy Source

Pathway Synthetic

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