5beta-Androstane-3,17-dione (BioCAD00000005079)

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Metabolite Card

Formula: C19H28O2 (288.2089)
SMILES: [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C

Synonyms [en]

Etiocholanedione; 5beta-androstane-3,17-dione; Etiocholane-3,17-dione; 5b-Androstanedione; (5b)-Androstane-3,17-dione; Etiochola-3,17-dione

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

5beta-Androstane-3,17-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: BioCAD00000005079). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Etiocholanedione is a 5-beta metabolite product of the catabolism of androgens. Etiocholanedione has been identified as a ketosteroid and isolated from the urine of healthy and diseased persons. Etiocholanedione has been identified as a metabolite of an altered androgen metabolism that eventually leads hepatocellular carcinoma to impaired hormone responsiveness in human. Etiocholanedione has been identified as a metabolite of 17alpha-hydroxyprogesterone in some patients affected by congenital adrenal hyperplasia, although it doesn't appear to account for the masculinization observed in congenital hyperplasia. Etiocholanedione can be the product of microbial contamination of urine since a few organisms are able to synthesize it using endogenous steroids as substrates. Human axillary bacteria are able to produce small amounts of etiocholanedione from testosterone. (PMID: 12161001, 13795320, 11161304, 2026727). Etiocholanedione has been found to be a metabolite of Corynebacterium (PMID: 11161304).

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 1229-12-5
  • PubChem: 440114
  • ChEBI: ChEBI:16985
  • HMDB: HMDB0003769
  • HMDB: HMDB03769
  • LipidMaps: LMST02020058
  • KEGG: C03772
  • BioCyc: 5-BETA-ANDROSTANE-317-DIONE
  • Wikipedia: Etiocholanedione
  • DrugBank: DB07375
  • MoNA: HMDB0003769_c_ms_99826
  • MoNA: HMDB0003769_c_ms_99827
  • Metlin: METLIN_41855

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R01835 1.3.1.3 5beta-androstane-3,17-dione:NADP+ 4,5-oxidoreductase
KEGG:R04309 1.1.1.50 3alpha-hydroxy-5beta-androstan-17-one:NAD+ oxidoreductase (B-specific)
KEGG:R04310 1.1.1.50 3alpha-hydroxy-5beta-androstan-17-one:NADP+ oxidoreductase (B-specific)
Rhea:RHEA:10357 1.1.1.152 3α-hydroxy-5β-androstan-17-one + NAD+ => 5β-androstane-3,17-dione + NADH + H+
Rhea:RHEA:10358 1.1.1.152 5β-androstane-3,17-dione + NADH + H+ => 3α-hydroxy-5β-androstan-17-one + NAD+
Rhea:RHEA:10359 1.1.1.152 3α-hydroxy-5β-androstan-17-one + NAD+ <=> 5β-androstane-3,17-dione + NADH + H+
Rhea:RHEA:46657 androst-4-ene-3,17-dione + NADPH + H+ => 5β-androstane-3,17-dione + NADP+
Rhea:RHEA:46658 5β-androstane-3,17-dione + NADP+ => androst-4-ene-3,17-dione + NADPH + H+
Rhea:RHEA:46659 androst-4-ene-3,17-dione + NADPH + H+ <=> 5β-androstane-3,17-dione + NADP+
Rhea:RHEA:69037 5β-androstane-3,17-dione + NADPH + H+ => 3β-hydroxy-5β-androstane-17-one + NADP+
Rhea:RHEA:69038 3β-hydroxy-5β-androstane-17-one + NADP+ => 5β-androstane-3,17-dione + NADPH + H+
Rhea:RHEA:69039 5β-androstane-3,17-dione + NADPH + H+ <=> 3β-hydroxy-5β-androstane-17-one + NADP+
BioCyc:RXN-16513 1.3.1.- ANDROST4ENE + NADPH + PROTON --> 5-BETA-ANDROSTANE-317-DIONE + NADP
BioCyc:1.1.1.152-RXN 1.1.1.152 3-ALPHA-HYDROXY-5-BETA-ANDROSTAN-17-ONE + NAD<=>PROTON + 5-BETA-ANDROSTANE-317-DIONE + NADH
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
WikiPathways:WP3604 Biochemical pathways: part I
PathBank:SMP0030406 Androstenedione Metabolism
PathBank:SMP0087530 Androstenedione Metabolism
PathBank:SMP0087421 Androstenedione Metabolism
PathBank:SMP0087364 Androstenedione Metabolism
PathBank:SMP0063688 Androstenedione Metabolism
PathBank:SMP0087271 Androstenedione Metabolism
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