Androstenedione (BioCAD00000006571)

blood cerebrospinal fluid (csf) urine adipose tissue adrenal cortex adrenal gland epidermis fibroblasts kidney liver ovary placenta prostate skeletal muscle testis plant natural products microbial natural products

Metabolite Card

Formula: C19H26O2 (286.1933)
SMILES: [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

Synonyms [en]

androstenedione; Androst-4-ene-3,17-dione; 4-Androstene-3,17-dione; 4-ANDROSTENE-3-17-DIONE; 4-Androstenedione; delta-4-Androstenedione

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Androstenedione. 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: BioCAD00000006571). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Androstenedione is a delta-4 19-carbon steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. It is the common precursor of male and female sex hormones. Some androstenedione is also secreted into the plasma and may be converted in peripheral tissues to testosterone and estrogens. Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. It is further converted to either testosterone or estrone. The production of adrenal androstenedione is governed by ACTH, while the production of gonadal androstenedione is under control by gonadotropins.

Cytoplasm Extracellular Membrane Endoplasmic reticulum
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 117598-81-9
  • CAS Registry Number: 63-05-8
  • CAS Registry Number: 897039-79-1
  • PubChem: 2193
  • PubChem: 6128
  • PubChem: 6432604
  • ChEBI: ChEBI:16422
  • HMDB: HMDB0000053
  • LipidMaps: LMST02020007
  • KEGG: C00280
  • BioCyc: ANDROST4ENE
  • NCBI MeSH: Androstenedione
  • Wikipedia: Androstenedione
  • DrugBank: DB01536
  • RefMet: RM0159794
  • MoNA: AU280301
  • MoNA: AU280302
  • MoNA: AU280303
  • MoNA: AU280304
  • MoNA: AU280305
  • MoNA: AU280306
  • MoNA: CB000375
  • MoNA: FFF00258
  • MoNA: FFF00259
  • MoNA: FFF00260
  • MoNA: FFF00261
  • MoNA: FFF00262
  • MoNA: FFF00263
  • MoNA: FFF00264
  • MoNA: FiehnHILIC000193
  • MoNA: FiehnLib000155
  • MoNA: FiehnLib000156
  • MoNA: HMDB0000053_c_ms_2118
  • MoNA: HMDB0000053_c_ms_2121
  • MoNA: HMDB0000053_ms_ms_84
  • MoNA: HMDB0000053_ms_ms_85
  • MoNA: HMDB0000053_ms_ms_86
  • MoNA: JP005721
  • MoNA: JP011413
  • MoNA: LU039601
  • MoNA: LU039602
  • MoNA: LU039603
  • MoNA: LU039604
  • MoNA: LU039605
  • MoNA: SM873201
  • MoNA: UF416501
  • MoNA: UF416502
  • MoNA: UF416503
  • MoNA: UF416504
  • Metlin: METLIN_2795
  • Coconut NaturalProduct: CNP0118298.1
  • Coconut NaturalProduct: CNP0267219.1
  • Coconut NaturalProduct: CNP0378301.1
  • Coconut NaturalProduct: CNP0378301.2
  • Coconut NaturalProduct: CNP0378301.5

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R01833 1.14.99.12 androst-4-ene-3,17-dione,hydrogen-donor:oxygen oxidoreductase (13-hydroxylating, lactonizing)
KEGG:R01834 1.3.99.5 3-oxo-5alpha-steroid:(acceptor) delta4-oxidoreductase
KEGG:R01835 1.3.1.3 5beta-androstane-3,17-dione:NADP+ 4,5-oxidoreductase
KEGG:R01836 1.1.1.51 testosterone:NAD+ 17-oxidoreductase
KEGG:R01837 1.1.1.145 3beta-hydroxyandrost-5-en-17-one:NAD+ 3-oxidoreductase/delta5-delta-4 isomerase
KEGG:R01838 1.1.1.51 testosterone:NADP+ 17-oxidoreductase
KEGG:R01840 1.14.14.14 androstenedione,NADPH---hemoprotein reductase:oxygen oxidoreductase (19-hydroxylating)
KEGG:R01842 1.14.14.1 androstenedione,NADPH---hemoprotein reductase:oxygen oxidoreductase (7alpha-hydroxylating)
KEGG:R02725 1.14.15.4 androstenedione,reduced-adrenal-ferredoxin:oxygen oxidoreductase (11-hydroxylating)
KEGG:R08205 1.14.13.54 C00280 + C00005 + C00080 + C00007<=>C04676 + C00006 + C00001
KEGG:R08206 1.14.13.54 C01176 + C00005 + C00080 + C00007<=>C00280 + C00033 + C00006 + C00001
KEGG:R08518 1.14.14.32 17alpha-hydroxyprogesterone,NADPH---hemoprotein reductase:oxygen oxidoreductase (17alpha-hydroxylating, acetate-releasing)
KEGG:R09884 1.3.99.4 androstenedione:acceptor Delta1-oxidoreductase
KEGG:R09919 C21076<=>C00280
KEGG:R09955 5.3.3.1 5-androstene-3,17-dione delta5-delta4-isomerase
KEGG:R10242 1.3.1.22 5alpha-androstane-3,17-dione:NADP+ delta4-oxidoreductase
KEGG:R10515 1.14.14.14 androst-4-ene-3,17-dione monooxygenase (estrone-forming)
KEGG:R13474 4.1.3.- C23019<=>C00280 + C00100
Rhea:RHEA:14754 1.14.14.19 17α-hydroxyprogesterone + reduced [NADPH—hemoprotein reductase] + O2 => androst-4-ene-3,17-dione + acetate + oxidized [NADPH—hemoprotein reductase] + H2O + 2 H+
Rhea:RHEA:14755 1.14.14.19 androst-4-ene-3,17-dione + acetate + oxidized [NADPH—hemoprotein reductase] + H2O + 2 H+ => 17α-hydroxyprogesterone + reduced [NADPH—hemoprotein reductase] + O2
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Organism Source

Taxonomy Source

  1. Hugonia busseana [ncbi taxid: 586373]
  2. Alcea rosea [ncbi taxid: 65557]
  3. Alcyonium utinomii [ncbi taxid: ]
  4. Aldisa sanguinea [ncbi taxid: 2049529]
  5. Alpinia blepharocalyx [ncbi taxid: 105668]
  6. Anguilla japonica [ncbi taxid: 7937]
  7. Aonidiella aurantii [ncbi taxid: 30082]
  8. Aplysina archeri [ncbi taxid: 289390]
  9. Araiostegiella perdurans [ncbi taxid: ]
  10. Aspergillus carneus [ncbi taxid: 41282]
  11. Aspergillus striatus [ncbi taxid: 469280]
  12. Balanops australiana [ncbi taxid: 1118758]
  13. Cortinarius odoratus [ncbi taxid: ]
  14. Curcuma aromatica [ncbi taxid: 136209]
  15. Daphnia magna [ncbi taxid: 35525]
  16. Eleutherobia albiflora [ncbi taxid: ]
  17. Eucalyptus jenseni [ncbi taxid: ]
  18. Euonymus tingens [ncbi taxid: 1089406]
  19. Euphorbia cornigera [ncbi taxid: 2510634]
  20. Euphorbia tithymaloides [ncbi taxid: 212310]
  21. Gymnopus confluens [ncbi taxid: ]
  22. Halla parthenopeia [ncbi taxid: ]
  23. Homo sapiens [ncbi taxid: 9606]
  24. Hylocomium splendens [ncbi taxid: 53007]
  25. Kokoona reflexa [ncbi taxid: 1504447]
  26. Lilium lancifolium [ncbi taxid: 79002]
  27. Linum usitatissimum [ncbi taxid: 4006]
  28. Macrolepiota neomastoidea [ncbi taxid: ]
  29. Maesa ramentacea [ncbi taxid: 1526298]
  30. Melolontha melolontha [ncbi taxid: 7061]
  31. Millettia laurentii [ncbi taxid: 2747815]
  32. Monodora tenuifolia [ncbi taxid: 306973]
  33. Mus musculus [ncbi taxid: 10090]
  34. Nototodarus sloanii [ncbi taxid: 215440]
  35. Ocimum tenuiflorum [ncbi taxid: 204149]
  36. Penicillium janczewskii [ncbi taxid: 121612]
  37. Pinus strobus [ncbi taxid: 3348]
  38. Pinus sylvestris [ncbi taxid: 3349]
  39. Pluchea odorata [ncbi taxid: 1548633]
  40. Pseudoplexaura flagellosa [ncbi taxid: 287903]
  41. Salacia lehmbachii [ncbi taxid: 213839]
  42. Salvia yosgadensis [ncbi taxid: 1933769]
  43. Sideritis brevibracteata [ncbi taxid: ]
  44. Sideroxylon cubense [ncbi taxid: 362723]
  45. Viguiera decurrens [ncbi taxid: 1048926]
  46. Streptomyces hydrogenans [ncbi taxid: 1873719]

Pathway Synthetic

pathway id name
BioCyc:HUMAN_PWY66-378 androgen biosynthesis
BioCyc:META_PWY66-380 estradiol biosynthesis I (via estrone)
BioCyc:MTBH37RV_PWY-6946 cholesterol degradation to androstenedione II (cholesterol dehydrogenase)
BioCyc:MTBCDC1551_PWY-6943 testosterone and androsterone degradation to androstendione
BioCyc:META_PWY-6946 cholesterol degradation to androstenedione II (cholesterol dehydrogenase)
BioCyc:META_PWY-6937 superpathway of testosterone and androsterone degradation
BioCyc:MTBCDC1551_PWY-6937 superpathway of testosterone and androsterone degradation
BioCyc:HUMAN_PWY66-380 estradiol biosynthesis I
BioCyc:META_PWY66-378 androgen biosynthesis
BioCyc:META_PWY-6944 androstenedione degradation
BioCyc:MTBH37RV_PWY-6947 superpathway of cholesterol degradation II (cholesterol dehydrogenase)
BioCyc:MTBH37RV_PWY-6945 cholesterol degradation to androstenedione I (cholesterol oxidase)
BioCyc:MTBCDC1551_PWY-6947 superpathway of cholesterol degradation II (cholesterol dehydrogenase)
BioCyc:MTBCDC1551_PWY-6945 cholesterol degradation to androstenedione I (cholesterol oxidase)
BioCyc:META_PWY-6947 superpathway of cholesterol degradation II (cholesterol dehydrogenase)
BioCyc:META_PWY-6928 superpathway of cholesterol degradation I (cholesterol oxidase)
BioCyc:META_PWY-6945 cholesterol degradation to androstenedione I (cholesterol oxidase)
BioCyc:META_PWY-6943 testosterone and androsterone degradation to androstendione
BioCyc:META_PWY-6948 sitosterol degradation to androstenedione
BioCyc:MTBH37RV_PWY-6944 androstenedione degradation
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