CHEBI:17347 - testosterone

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ChEBI Name testosterone
ChEBI ID CHEBI:17347
Definition An androstanoid having 17β-hydroxy and 3-oxo groups, together with unsaturation at C-4‒C-5..
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45798, CHEBI:9461, CHEBI:15214, CHEBI:26883
Supplier Information ZINC000013508431
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Testosterone is the primary male sex hormone and androgen in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testicles and prostate, as well as promoting secondary sexual characteristics such as increased muscle and bone mass, and the growth of body hair. It is associated with increased aggression, sex drive, dominance, courtship display, and a wide range of behavioral characteristics. In addition, testosterone in both sexes is involved in health and well-being, where it has a significant effect on overall mood, cognition, social and sexual behavior, metabolism and energy output, the cardiovascular system, and in the prevention of osteoporosis. Insufficient levels of testosterone in men may lead to abnormalities including frailty, accumulation of adipose fat tissue within the body, anxiety and depression, sexual performance issues, and bone loss. Excessive levels of testosterone in men may be associated with hyperandrogenism, higher risk of heart failure, increased mortality in men with prostate cancer, and male pattern baldness. Testosterone is a steroid hormone from the androstane class containing a ketone and a hydroxyl group at positions three and seventeen respectively. It is biosynthesized in several steps from cholesterol and is converted in the liver to inactive metabolites. It exerts its action through binding to and activation of the androgen receptor. In humans and most other vertebrates, testosterone is secreted primarily by the testicles of males and, to a lesser extent, the ovaries of females. On average, in adult males, levels of testosterone are about seven to eight times as great as in adult females. As the metabolism of testosterone in males is more pronounced, the daily production is about 20 times greater in men. Females are also more sensitive to the hormone. In addition to its role as a natural hormone, testosterone is used as a medication to treat hypogonadism and breast cancer. Since testosterone levels decrease as men age, testosterone is sometimes used in older men to counteract this deficiency. It is also used illicitly to enhance physique and performance, for instance in athletes. The World Anti-Doping Agency lists it as S1 Anabolic agent substance "prohibited at all times".
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Formula C19H28O2
Net Charge 0
Average Mass 288.42440
Monoisotopic Mass 288.20893
InChI InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
InChIKey MUMGGOZAMZWBJJ-DYKIIFRCSA-N
SMILES [H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@H](O)CC[C@@]21[H]
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Daphnia magna (NCBI:txid35525) See: Changes in the Metabolic Elimination Profile of Testosterone Following Exposure of the Crustacean Daphnia magna to TributyltinGerald A. LeBlanc and James B. McLachlanEcotoxicology and Environmental Safety 45, 296-303 (2000)
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): androgen
A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors.
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing testosterone (CHEBI:17347) has role Daphnia magna metabolite (CHEBI:83056)
testosterone (CHEBI:17347) has role androgen (CHEBI:50113)
testosterone (CHEBI:17347) has role human metabolite (CHEBI:77746)
testosterone (CHEBI:17347) has role mouse metabolite (CHEBI:75771)
testosterone (CHEBI:17347) is a 17β-hydroxy steroid (CHEBI:35343)
testosterone (CHEBI:17347) is a 3-oxo-Δ4 steroid (CHEBI:47909)
testosterone (CHEBI:17347) is a androstanoid (CHEBI:50402)
testosterone (CHEBI:17347) is a C19-steroid (CHEBI:131621)
Incoming 1α-hydroxytestosterone (CHEBI:132358) has functional parent testosterone (CHEBI:17347)
1β-hydroxytestosterone (CHEBI:137076) has functional parent testosterone (CHEBI:17347)
11β-hydroxytestosterone (CHEBI:81481) has functional parent testosterone (CHEBI:17347)
11-oxotestosterone (CHEBI:34133) has functional parent testosterone (CHEBI:17347)
15α-hydroxytestosterone (CHEBI:34161) has functional parent testosterone (CHEBI:17347)
16α-hydroxytestosterone (CHEBI:34172) has functional parent testosterone (CHEBI:17347)
16β-fluoro-17β-hydroxyandrost-4-en-3-one propionate (CHEBI:79755) has functional parent testosterone (CHEBI:17347)
16β-hydroxytestosterone (CHEBI:83027) has functional parent testosterone (CHEBI:17347)
19-hydroxytestosterone (CHEBI:798) has functional parent testosterone (CHEBI:17347)
19-oxotestosterone (CHEBI:75308) has functional parent testosterone (CHEBI:17347)
2α-fluoro-17β-hydroxyandrost-4-en-3-one (CHEBI:79778) has functional parent testosterone (CHEBI:17347)
2α-hydroxytestosterone (CHEBI:83025) has functional parent testosterone (CHEBI:17347)
2-hydroxytestosterone (CHEBI:86013) has functional parent testosterone (CHEBI:17347)
6β-hydroxytestosterone (CHEBI:34477) has functional parent testosterone (CHEBI:17347)
6-dehydrotestosterone (CHEBI:29117) has functional parent testosterone (CHEBI:17347)
7α -hydroxytestosterone (CHEBI:2295) has functional parent testosterone (CHEBI:17347)
ethisterone (CHEBI:34749) has functional parent testosterone (CHEBI:17347)
glucosyltestosterone (CHEBI:83022) has functional parent testosterone (CHEBI:17347)
methyltestosterone (CHEBI:27436) has functional parent testosterone (CHEBI:17347)
testosterone 17-glucosiduronic acid (CHEBI:28835) has functional parent testosterone (CHEBI:17347)
testosterone 3-(O-carboxymethyl)oxime (CHEBI:60297) has functional parent testosterone (CHEBI:17347)
testosterone acetate (CHEBI:16524) has functional parent testosterone (CHEBI:17347)
testosterone cypionate (CHEBI:9463) has functional parent testosterone (CHEBI:17347)
testosterone enanthate (CHEBI:9464) has functional parent testosterone (CHEBI:17347)
testosterone-3-CMO-Hist (CHEBI:60303) has functional parent testosterone (CHEBI:17347)
IUPAC Name
17β-hydroxyandrost-4-en-3-one
INNs Sources
testosterona ChemIDplus
testosterone ChemIDplus
testosteronum ChemIDplus
Synonyms Sources
17beta-hydroxy-4-androsten-3-one ChEBI
17beta-Hydroxy-4-androsten-3-one KEGG COMPOUND
4-androsten-17β-ol-3-one NIST Chemistry WebBook
Androderm ChemIDplus
Testosteron ChemIDplus
Testosterone KEGG COMPOUND
TESTOSTERONE PDBeChem
testosterone UniProt
Manual Xrefs Databases
2607 DrugCentral
C00003675 KNApSAcK
C00535 KEGG COMPOUND
D00075 KEGG DRUG
DB00624 DrugBank
HMDB0000234 HMDB
LMST02020002 LIPID MAPS
TES PDBeChem
Testosterone Wikipedia
View more database links
Registry Numbers Types Sources
1915399 Reaxys Registry Number Reaxys
3653705 Beilstein Registry Number Beilstein
538843 Gmelin Registry Number Gmelin
58-22-0 CAS Registry Number ChemIDplus
58-22-0 CAS Registry Number NIST Chemistry WebBook
Citations
Hadeed NN, Thanoon IA, Al-Mukhtar SB (2014)
Total testosterone levels and the effect of sildenafil on type 2 diabetics with erectile dysfunction.
Oman medical journal 29, 46-50 [PubMed:24498482]
[show Abstract]
Howell S, Shalet S (2001)
Testosterone deficiency and replacement.
Hormone research 56 Suppl 1, 86-92 [PubMed:11786693]
[show Abstract]
Ball WJ, Kasturi R, Dey P, Tabet M, O'Donnell S, Hudson D, Fishwild D (1999)
Isolation and characterization of human monoclonal antibodies to digoxin.
Journal of immunology (Baltimore, Md. : 1950) 163, 2291-2298 [PubMed:10438974]
[show Abstract]
McGAVACK TH (1947)
Hormones and the aging process; testosterone.
New York medicine 3, 15-18 [PubMed:18900503]
Last Modified
10 April 2018