5beta-Pregnane-3,20-dione (BioCAD00000005087)

blood

Metabolite Card

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

Synonyms [en]

5beta-Pregnane-3,20-dione; 5beta-Dihydroprogesterone; 3,20-Pregnanedione; 5beta-Pregnan-3,20-dione; (5BETA)-PREGNANE-3,20-DIONE; 5b-dihydroprogesterone

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

5beta-Pregnane-3,20-dione. 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: BioCAD00000005087). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

(5beta)-pregnane-3,20-dione, also known as 3,20-pregnanedione or 5beta-dihydroprogesterone, belongs to gluco/mineralocorticoids, progestogins and derivatives class of compounds. Those are steroids with a structure based on a hydroxylated prostane moiety. Thus, (5beta)-pregnane-3,20-dione is considered to be a steroid lipid molecule (5beta)-pregnane-3,20-dione is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (5beta)-pregnane-3,20-dione can be found in a number of food items such as opium poppy, walnut, rowal, and italian sweet red pepper, which makes (5beta)-pregnane-3,20-dione a potential biomarker for the consumption of these food products.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 128-23-4
  • PubChem: 92745
  • ChEBI: ChEBI:30154
  • HMDB: HMDB0304221
  • HMDB: HMDB0304221_cms_2189
  • LipidMaps: LMST02030146
  • KEGG: C05479
  • Wikipedia: 5%CE%B2-Dihydroprogesterone
  • DrugBank: DB07557
  • RefMet: RM0135775
  • Metlin: METLIN_57844
  • Coconut NaturalProduct: CNP0201363.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02215 1.3.99.6 5beta-pregnane-3,20-dione:(acceptor) delta4-oxidoreductase
KEGG:R02219 1.3.1.3 3-oxo-5beta-steroid:NADP+ delta4-oxidoreductase;
KEGG:R04845 1.1.1.50 3alpha-hydroxy-5beta-pregnane-20-one:NAD+ oxidoreductase (B-specific)
KEGG:R04846 1.1.1.50 3alpha-hydroxy-5beta-pregnane-20-one:NADP+ oxidoreductase (B-specific)
KEGG:R06166 1.1.1.277 3beta-hydroxy-5beta-steroid:NADP+ 3-oxidoreductase
Rhea:RHEA:22945 1.1.1.277 3β-hydroxy-5β-pregnane-20-one + NADP+ => 5β-pregnan-3,20-dione + NADPH + H+
Rhea:RHEA:22946 1.1.1.277 5β-pregnan-3,20-dione + NADPH + H+ => 3β-hydroxy-5β-pregnane-20-one + NADP+
Rhea:RHEA:22947 1.1.1.277 3β-hydroxy-5β-pregnane-20-one + NADP+ <=> 5β-pregnan-3,20-dione + NADPH + H+
Rhea:RHEA:42169 20α-hydroxy-5β-pregnan-3-one + NADP+ => 5β-pregnan-3,20-dione + NADPH + H+
Rhea:RHEA:42170 5β-pregnan-3,20-dione + NADPH + H+ => 20α-hydroxy-5β-pregnan-3-one + NADP+
Rhea:RHEA:42171 20α-hydroxy-5β-pregnan-3-one + NADP+ <=> 5β-pregnan-3,20-dione + NADPH + H+
Rhea:RHEA:46661 progesterone + NADPH + H+ => 5β-pregnan-3,20-dione + NADP+
Rhea:RHEA:46662 5β-pregnan-3,20-dione + NADP+ => progesterone + NADPH + H+
Rhea:RHEA:46663 progesterone + NADPH + H+ <=> 5β-pregnan-3,20-dione + NADP+
Rhea:RHEA:69017 3α-hydroxy-5β-pregnan-20-one + NADP+ => 5β-pregnan-3,20-dione + NADPH + H+
Rhea:RHEA:69018 5β-pregnan-3,20-dione + NADPH + H+ => 3α-hydroxy-5β-pregnan-20-one + NADP+
Rhea:RHEA:69019 3α-hydroxy-5β-pregnan-20-one + NADP+ <=> 5β-pregnan-3,20-dione + 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
BioCyc:HUMAN_PWY-6032 cardenolide biosynthesis
BioCyc:META_PWY-6032 cardenolide biosynthesis
PlantCyc:PLANT_PWY-6032 cardenolide biosynthesis
WikiPathways:WP4523 Classical pathway of steroidogenesis with glucocorticoid and mineralocorticoid metabolism
WikiPathways:WP5277 Steroid hormone precursor biosynthesis
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