Androsta-1,4-diene-3,17-dione (BioCAD00000006564)

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Metabolite Card

Formula: C19H24O2 (284.1776)
SMILES: [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C

Synonyms [en]

androsta-1,4-diene-3,17-dione; ANDROSTA-1,4-DIEN-3,17-DIONE; 1-Dehydroandrostenedione; Androstadienedione; boldione; 1,4-androstadiene-3,17-dione

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Androsta-1,4-diene-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: BioCAD00000006564). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Boldione is a direct precursor (prohormone) to the anabolic steroid boldenone (1,4-androstadiene-17beta-ol-3-one). It is advertised as a highly anabolic/androgenic compound promoting muscularity, enhancing strength and overall physical performance, and is available on the Internet and in health stores. Conflicting findings regarding the boldenone content of bovine faeces suggest it may be synthesized de novo in emitted faeces. Boldione is the oxidized form of boldenone, an this anabolic steroid is forbidden in EU countries in calves and bulls bred for meat production, and is illegally used as growth promoters, as they improve the growth and feed conversion in food producing animals. (PMID: 16449054, 16308875, 16244993).

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 593235-02-0
  • CAS Registry Number: 897-06-3
  • PubChem: 13472
  • ChEBI: ChEBI:40799
  • HMDB: HMDB0003422
  • KEGG: C20144
  • BioCyc: CPD-13704
  • NCBI MeSH: 1,4-androstadiene-3,17-dione
  • Wikipedia: Boldione
  • DrugBank: DB07373
  • RefMet: RM0128381
  • MoNA: Bruker_HCD_library001516
  • MoNA: Bruker_HCD_library001517
  • MoNA: CCMSLIB00001059058
  • MoNA: FFF00050
  • MoNA: FFF00051
  • MoNA: FFF00052
  • MoNA: FFF00053
  • MoNA: FFF00054
  • MoNA: FFF00055
  • MoNA: FFF00056
  • MoNA: FFF00057
  • MoNA: FFF00058
  • MoNA: FFF00059
  • MoNA: FFF00060
  • MoNA: FFF00061
  • MoNA: FFF00062
  • MoNA: VF-NPL-LTQ006790
  • MoNA: VF-NPL-LTQ006791
  • MoNA: VF-NPL-LTQ006792
  • MoNA: VF-NPL-QTOF006650
  • MoNA: VF-NPL-QTOF006651
  • MoNA: VF-NPL-QTOF006652
  • Metlin: METLIN_44529
  • Coconut NaturalProduct: CNP0108557.0
  • Coconut NaturalProduct: CNP0217348.0
  • Coconut NaturalProduct: CNP0282764.1
  • Coconut NaturalProduct: CNP0282764.3
  • Coconut NaturalProduct: CNP0282764.4

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R09860 1.14.15.30 androsta-1,4-diene-3,17-dione,[reduced ferredoxin]:oxygen oxidoreductase (9alpha-hydroxylating)
KEGG:R09884 1.3.99.4 androstenedione:acceptor Delta1-oxidoreductase
Rhea:RHEA:32200 1.14.15.30 androsta-1,4-diene-3,17-dione + 2 reduced [2Fe-2S]-[ferredoxin] + O2 + 2 H+ => 9α-hydroxyandrosta-1,4-diene-3,17-dione + 2 oxidized [2Fe-2S]-[ferredoxin] + H2O
Rhea:RHEA:32201 1.14.15.30 9α-hydroxyandrosta-1,4-diene-3,17-dione + 2 oxidized [2Fe-2S]-[ferredoxin] + H2O => androsta-1,4-diene-3,17-dione + 2 reduced [2Fe-2S]-[ferredoxin] + O2 + 2 H+
Rhea:RHEA:32202 1.14.15.30 androsta-1,4-diene-3,17-dione + 2 reduced [2Fe-2S]-[ferredoxin] + O2 + 2 H+ <=> 9α-hydroxyandrosta-1,4-diene-3,17-dione + 2 oxidized [2Fe-2S]-[ferredoxin] + H2O
Rhea:RHEA:51057 1.3.99.4 androst-4-ene-3,17-dione + A => androsta-1,4-diene-3,17-dione + AH2
Rhea:RHEA:51058 1.3.99.4 androsta-1,4-diene-3,17-dione + AH2 => androst-4-ene-3,17-dione + A
Rhea:RHEA:51059 1.3.99.4 androst-4-ene-3,17-dione + A <=> androsta-1,4-diene-3,17-dione + AH2
Rhea:RHEA:51061 1.3.99.5 5α-androst-1-ene-3,17-dione + A => androsta-1,4-diene-3,17-dione + AH2
Rhea:RHEA:51062 1.3.99.5 androsta-1,4-diene-3,17-dione + AH2 => 5α-androst-1-ene-3,17-dione + A
Rhea:RHEA:51063 1.3.99.5 5α-androst-1-ene-3,17-dione + A <=> androsta-1,4-diene-3,17-dione + AH2
BioCyc:RXN-12714 1.3.99.4 ANDROST4ENE + Acceptor --> CPD-13704 + Donor-H2
BioCyc:RXN-12691 1.14.15.30 CPD-13704 + OXYGEN-MOLECULE + 2 Reduced-ferredoxins + 2 PROTON --> CPD-13680 + 2 Oxidized-ferredoxins + WATER
BioCyc:RXN-21463 1.3.99.5 CPD-13704 + Donor-H2 --> CPD-23354 + Acceptor
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Organism Source

Taxonomy Source

  1. Chaenomeles sinensis [ncbi taxid: ]
  2. Neorautanenia mitis [ncbi taxid: 167620]
  3. Pterocella vesiculosa [ncbi taxid: 2780185]
  4. Relhania fruticosa [ncbi taxid: ]
  5. Plumbago zeylanica [ncbi taxid: 76149]
  6. Aglaia rubiginosa [ncbi taxid: 1475121]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-6937 superpathway of testosterone and androsterone degradation
BioCyc:MTBCDC1551_PWY-6937 superpathway of testosterone and androsterone degradation
BioCyc:META_PWY-6944 androstenedione degradation
BioCyc:MTBH37RV_PWY-6947 superpathway of cholesterol degradation II (cholesterol dehydrogenase)
BioCyc:MTBCDC1551_PWY-6947 superpathway of cholesterol degradation II (cholesterol dehydrogenase)
BioCyc:META_PWY-6947 superpathway of cholesterol degradation II (cholesterol dehydrogenase)
BioCyc:META_PWY-6928 superpathway of cholesterol degradation I (cholesterol oxidase)
BioCyc:MTBH37RV_PWY-6944 androstenedione degradation
BioCyc:MTBCDC1551_PWY-6944 androstenedione degradation
View All Pathways