testosterone (CHEBI:17347)

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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	ChemicalBook:CB5380541, eMolecules:511977, ZINC000118912393

Download	Molfile XML SDF

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Molfile

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M END): 20 ms

reading 49 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

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49 atoms created

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Wikipedia	License
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".
Read full article at Wikipedia

Formula

C19H28O2

Net Charge

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]

Objectives

Hypotestosteronemia has been reported in approximately half of type 2 diabetic men in general. This study aims to assess serum total testosterone levels in type 2 diabetics with erectile dysfunction and to correlate the degree of improvement between sildenafil citrate and testosterone levels.

Methods

A cross sectional and prospective comparative interventional study was conducted at the Diabetic Clinic of Assalam Teaching Hospital in Mosul, during the period from January 1, 2009 through to December 31, 2011. The study enrolled 120 type 2 diabetic males with erectile dysfunction who were analyzed with regard to age, duration of diabetes, duration and severity of erectile dysfunction, serum total testosteron levels and the degree of response to sildenafil citrate in terms of testosterone levels. The data were statistically analyzed using the independent two-sample Student t test, χ (2) test and Pearson correlation test. A p-value of <0.05 was considered statistically significant.

Results

Thirty six percent of type 2 diabetic males with erectile dysfunction were found to have low serum testosterone levels. The hypotestosteronemic and normotestosteronemic subgroups were not significantly different in terms of mean age, duration of diabetes, reduction of libido, and reduction in erectile function. The rate and the degree of improvement of erection by sildenafil in the normo-and-hypotestosteronemic respondents were not significantly different, but the degree of improvement by sildenafil was significantly correlated to testosterone levels among the hypotestosteronemic group.

Conclusion

Hypotestosteronemia was found in 36% of type 2 diabetic males with erectile dysfunction. The degree of improvement of erectile dysfunction by sildenafil was directly proportional to the serum testosterone levels among the hypotestosteronemic group. Therapeutic supplement with testosterone preparation in the hypotestosteronemic diabetics with erectile dysfunction may improve their response to sildenafil.

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

CHEBI:17347 - testosterone

Objectives

Methods

Results

Conclusion

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