20alpha-Hydroxy-4-pregnen-3-one (BioCAD00000003198)

blood placenta testis

Metabolite Card

Formula: C21H32O2 (316.2402)
SMILES: [H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)O

Synonyms [en]

20alpha-Hydroxy-4-pregnen-3-one; 20alpha-Hydroxyprogesterone; 20alpha-Hydroxypregn-4-en-3-one; 20alpha-Dihydroprogesterone; Dihydroprogesterone; (S)-20-Hydroxypregn-4-en-3-one

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

20alpha-Hydroxy-4-pregnen-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: BioCAD00000003198). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

20alpha-Dihydroprogesterone is a biologically active 20-alpha-reduced metabolite of progesterone. It is converted from progesterone to 20-alpha-hydroxypregn-4-en-3-one by the 20-alpha-hydroxysteroid dehydrogenase in the corpus luteum and the placenta. Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation), and embryogenesis of humans and other species. Progesterone belongs to a class of hormones called progestagens, and is the major naturally occurring human progestagen (Wikipedia). During implantation and gestation, progesterone appears to decrease the maternal immune response to allow for the acceptance of the pregnancy. Progesterone decreases contractility of the uterine smooth muscle. The fetus metabolizes placental progesterone in the production of adrenal mineralo- and glucosteroids. A drop in progesterone levels is possibly one step that facilitates the onset of labour. In addition, progesterone inhibits lactation during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production (Wikipedia).

Cytoplasm Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 145-14-2
  • CAS Registry Number: 145-15-3
  • PubChem: 8956
  • PubChem: 92747
  • ChEBI: ChEBI:28453
  • ChEBI: ChEBI:36729
  • HMDB: HMDB0003069
  • LipidMaps: LMST02030153
  • LipidMaps: LMST02030169
  • KEGG: C04042
  • NCBI MeSH: 20-alpha-Dihydroprogesterone
  • Wikipedia: 20%CE%B2-Dihydroprogesterone
  • Wikipedia: 20α-Dihydroprogesterone
  • RefMet: RM0135776
  • Coconut NaturalProduct: CNP0323939.1

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02207 1.1.1.149 20alpha-hydroxy-4-pregnen-3-one:NAD+ 20-oxidoreductase
KEGG:R02209 1.1.1.149 20alpha-hydroxy-4-pregnen-3-one:NADP+ 20-oxidoreductase
Rhea:RHEA:42109 (20S)-hydroxypregn-4-en-3-one + NAD+ => progesterone + NADH + H+
Rhea:RHEA:42110 progesterone + NADH + H+ => (20S)-hydroxypregn-4-en-3-one + NAD+
Rhea:RHEA:42111 (20S)-hydroxypregn-4-en-3-one + NAD+ <=> progesterone + NADH + H+
Rhea:RHEA:42113 (20S)-hydroxypregn-4-en-3-one + NADP+ => progesterone + NADPH + H+
Rhea:RHEA:42114 progesterone + NADPH + H+ => (20S)-hydroxypregn-4-en-3-one + NADP+
Rhea:RHEA:42115 (20S)-hydroxypregn-4-en-3-one + NADP+ <=> progesterone + NADPH + H+
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Organism Source

Taxonomy Source

  1. Homo sapiens [ncbi taxid: 9606]
  2. Mus musculus [ncbi taxid: 10090]

Pathway Synthetic

pathway id name
WikiPathways:WP5277 Steroid hormone precursor biosynthesis
View All Pathways