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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:22 UTC
Update Date2021-09-14 15:40:23 UTC
HMDB IDHMDB0002961
Secondary Accession Numbers
  • HMDB02961
Metabolite Identification
Common NameDihydrotestosterone
DescriptionDihydrotestosterone is a potent androgenic metabolite of testosterone. Dihydrotestosterone (DHT) is generated by a 5-alpha reduction of testosterone. Unlike testosterone, DHT cannot be aromatized to estradiol therefore DHT is considered a pure androgenic steroid. -- Pubchem; Dihydrotestosterone (DHT) (INN: androstanolone) is a biologically active metabolite of the hormone testosterone, formed primarily in the prostate gland, testes, hair follicles, and adrenal glands by the enzyme 5-alpha-reductase by means of reducing the alpha 4,5 double-bond. Dihydrotestosterone belongs to the class of compounds called androgens, also commonly called androgenic hormones or testoids. DHT is thought to be approximately 30 times more potent than testosterone because of increased affinity to the androgen receptor.
Structure
Data?1582752259
Synonyms
ValueSource
17beta-Hydroxyandrostan-3-oneChEBI
4,5alpha-DihydrotestosteroneChEBI
5alpha-DHTChEBI
5alpha-DihydrotestosteroneChEBI
AndrostanolonaChEBI
AndrostanoloneChEBI
AndrostanolonumChEBI
DHTChEBI
DihydrotestosteronChEBI
StanoloneChEBI
17beta-Hydroxy-5alpha-androstan-3-oneKegg
AndractimKegg
17b-Hydroxyandrostan-3-oneGenerator
17Β-hydroxyandrostan-3-oneGenerator
4,5a-DihydrotestosteroneGenerator
4,5Α-dihydrotestosteroneGenerator
5a-DHTGenerator
5Α-DHTGenerator
5a-DihydrotestosteroneGenerator
5Α-dihydrotestosteroneGenerator
17b-Hydroxy-5a-androstan-3-oneGenerator
17Β-hydroxy-5α-androstan-3-oneGenerator
17beta-Hydroxy-3-oxo-5alpha-androstanoneHMDB
17b-Hydroxy-3-oxo-5a-androstanoneHMDB
17Β-hydroxy-3-oxo-5α-androstanoneHMDB
17-Hydroxy-androstan-3-oneHMDB
17-Hydroxyandrostan-3-oneHMDB
17b-Hydroxy-3-androstanoneHMDB
4-DihydrotestosteroneHMDB
5-a-AndrostanoloneHMDB
5-alpha-AndrostanoloneHMDB
5a-Androstan-17b-ol-3-oneHMDB
5a-Androstan-3-on-17b-olHMDB
5alpha-Androstan-17beta-ol-3-oneHMDB
5b-Androstan-3-on-17b-olHMDB
AnaboleenHMDB
AnabolexHMDB
AndroloneHMDB
AndrostaloneHMDB
Cristerona MBHMDB
DrolbanHMDB
NeodrolHMDB
ProteinaHMDB
ProtonaHMDB
StanaprolHMDB
StanoroneHMDB
17beta Hydroxy 5alpha androstan 3 oneHMDB
5 alpha DihydrotestosteroneHMDB
5 beta DihydrotestosteroneHMDB
5 beta-DihydrotestosteroneHMDB
Besins-iscovesco brand OF androstanoloneHMDB
5-alpha-DHTHMDB
AnaprotinHMDB
Berenguer infale brand OF androstanoloneHMDB
DihydroepitestosteroneHMDB
5 alpha DHTHMDB
5 alpha-DihydrotestosteroneHMDB
Besins iscovesco brand OF androstanoloneHMDB
Dihydrotestosterone, 5-alphaHMDB
17 beta Hydroxy 5 beta androstan 3 oneHMDB
17 beta-Hydroxy-5 beta-androstan-3-oneHMDB
5-alpha DihydrotestosteroneHMDB
Cuxson brand OF androstanoloneHMDB
GelovitHMDB
beta-Hydroxy-5 beta-androstan-3-one, 17HMDB
DIHYDROTESTOSTERONEChEBI
Chemical FormulaC19H30O2
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
IUPAC Name(1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
Traditional Name(1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
CAS Registry Number521-18-6
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H30O2/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/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyNVKAWKQGWWIWPM-ABEVXSGRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-oxosteroid
  • 3-oxo-5-alpha-steroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point181 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility525 mg/mL at 25 °CNot Available
LogP3.55HANSCH,C ET AL. (1995)
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP10(3.37) g/LALOGPS
logP10(3.41) g/LChemAxon
logS10(-4.5) g/LALOGPS
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.6 m³·mol⁻¹ChemAxon
Polarizability34.54 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.42731661259
DarkChem[M-H]-168.93731661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydrotestosterone,1TMS,#1C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C)CC[C@@H]122624.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrotestosterone,1TMS,#2C[C@]12CC[C@H]3[C@@H](CC[C@H]4CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@H]2O2596.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrotestosterone,1TMS,#3C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2O2578.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrotestosterone,1TBDMS,#1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C2887.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrotestosterone,1TBDMS,#2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]32)C12864.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrotestosterone,1TBDMS,#3CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC12823.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Dihydrotestosterone EI-B (Non-derivatized)splash10-015c-8970000000-ef0c6a4fd9c52be302842017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dihydrotestosterone EI-B (Non-derivatized)splash10-001l-1790000000-60cff73adc796876d4692017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dihydrotestosterone EI-B (Non-derivatized)splash10-015c-8970000000-ef0c6a4fd9c52be302842018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dihydrotestosterone EI-B (Non-derivatized)splash10-001l-1790000000-60cff73adc796876d4692018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrotestosterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gj-0390000000-9eeab8ff981af1be878c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrotestosterone GC-MS (1 TMS) - 70eV, Positivesplash10-001j-2129000000-dbb4c264166c851e22c12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrotestosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrotestosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-000x-9870000000-f6d80b2a53942c9af50b2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrotestosterone 30V, Positive-QTOFsplash10-0bta-0930000000-078d7455103eab0cf1ee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrotestosterone 40V, Positive-QTOFsplash10-08gj-0900000000-9f326ea5c1c454997fd32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrotestosterone 20V, Positive-QTOFsplash10-0a4i-0390000000-85c48da18cebca66ba3c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrotestosterone 10V, Positive-QTOFsplash10-0006-0090000000-f81b1315d55db1d47ec42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrotestosterone 50V, Positive-QTOFsplash10-02cv-0900000000-9d78808dd524e4ca6c502021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrotestosterone 30V, Positive-QTOFsplash10-0bta-0930000000-49751ee4f183943f62fa2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrotestosterone 10V, Positive-QTOFsplash10-00dl-0190000000-32b12edcbd16045a4a2e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrotestosterone 20V, Positive-QTOFsplash10-00dl-0390000000-a2704bedea3c7bf92d652016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrotestosterone 40V, Positive-QTOFsplash10-016r-2790000000-d1a3cc2c786b582339b32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrotestosterone 10V, Negative-QTOFsplash10-000i-0090000000-62e8fc46490b14aee68a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrotestosterone 20V, Negative-QTOFsplash10-000i-0090000000-d712d8c85325f4935c062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrotestosterone 40V, Negative-QTOFsplash10-05fu-2190000000-d8e9f38bc70955a04aea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrotestosterone 10V, Positive-QTOFsplash10-0006-0090000000-48f400d66433b81d9a662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrotestosterone 20V, Positive-QTOFsplash10-0aba-1950000000-acfc6238e1a13c48e8592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrotestosterone 40V, Positive-QTOFsplash10-066s-2900000000-1bc41566c7dc5d14c9032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrotestosterone 10V, Negative-QTOFsplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrotestosterone 20V, Negative-QTOFsplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrotestosterone 40V, Negative-QTOFsplash10-000i-0090000000-20b22a4e3152e3639e642021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Epidermis
  • Fibroblasts
  • Hair
  • Kidney
  • Liver
  • Neuron
  • Ovary
  • Prostate
  • Skeletal Muscle
  • Testis
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000172-0.00207 uMNewborn (0-30 days old)Female
Normal
details
BloodDetected and Quantified0.000200 - 0.00110 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.000860 - 0.00340 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.00041 +/- 0.00016 uMAdult (>18 years old)MaleNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0054 +/- 0.0028 uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.00006.89 uMNewborn (0-30 days old)Female
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
details
BloodDetected and Quantified0.000900-0.00390 uMAdult (>18 years old)MaleX-linked ichthyosis details
BloodDetected and Quantified0.0054 +/- 0.0029 uMAdult (>18 years old)Both
Psychiatric disorder
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0000010000 +/- 0.000004135 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00001275 +/- 0.00001792 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism with testosterone replacment details
Associated Disorders and Diseases
Disease References
Alcoholism
  1. Nieminen LR, Makino KK, Mehta N, Virkkunen M, Kim HY, Hibbeln JR: Relationship between omega-3 fatty acids and plasma neuroactive steroids in alcoholism, depression and controls. Prostaglandins Leukot Essent Fatty Acids. 2006 Oct-Nov;75(4-5):309-14. Epub 2006 Sep 7. [PubMed:16959481 ]
Major depressive disorder
  1. Nieminen LR, Makino KK, Mehta N, Virkkunen M, Kim HY, Hibbeln JR: Relationship between omega-3 fatty acids and plasma neuroactive steroids in alcoholism, depression and controls. Prostaglandins Leukot Essent Fatty Acids. 2006 Oct-Nov;75(4-5):309-14. Epub 2006 Sep 7. [PubMed:16959481 ]
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
  1. Kim CJ, Lin L, Huang N, Quigley CA, AvRuskin TW, Achermann JC, Miller WL: Severe combined adrenal and gonadal deficiency caused by novel mutations in the cholesterol side chain cleavage enzyme, P450scc. J Clin Endocrinol Metab. 2008 Mar;93(3):696-702. doi: 10.1210/jc.2007-2330. Epub 2008 Jan 8. [PubMed:18182448 ]
X-linked ichthyosis
  1. Lykkesfeldt G, Bennett P, Lykkesfeldt AE, Micic S, Moller S, Svenstrup B: Abnormal androgen and oestrogen metabolism in men with steroid sulphatase deficiency and recessive X-linked ichthyosis. Clin Endocrinol (Oxf). 1985 Oct;23(4):385-93. [PubMed:3864567 ]
Associated OMIM IDs
  • 608516 (Major depressive disorder)
  • 613743 (Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete)
  • 308100 (X-linked ichthyosis)
DrugBank IDDB02901
Phenol Explorer Compound IDNot Available
FooDB IDFDB023086
KNApSAcK IDNot Available
Chemspider ID10189
KEGG Compound IDC03917
BioCyc ID17-BETA-HYDROXY-5ALPHA-ANDROSTAN-3-O
BiGG ID42776
Wikipedia LinkDihydrotestosterone
METLIN ID2789
PubChem Compound10635
PDB IDNot Available
ChEBI ID16330
Food Biomarker OntologyNot Available
VMH ID5ADTSTSTERONE
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceGardi, Rinaldo; Castelli, Pier Paolo; Gandolfi, Roberto; Ercoli, Alberto. Conversion of 5a-pregnane-3,2O-dione to dihydrotestosterone. (1961), 1250-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tincello DG, Saunders PT, Hodgins MB, Simpson NB, Edwards CR, Hargreaves TB, Wu FC: Correlation of clinical, endocrine and molecular abnormalities with in vivo responses to high-dose testosterone in patients with partial androgen insensitivity syndrome. Clin Endocrinol (Oxf). 1997 Apr;46(4):497-506. [PubMed:9196614 ]
  2. Gratterola R: Anovulation and increased androgenic activity as breast cancer risk in women with fibrocystic disease of the breast. Cancer Res. 1978 Sep;38(9):3051-4. [PubMed:679211 ]
  3. Choi MH, Kim JN, Chung BC: Rapid HPLC-electrospray tandem mass spectrometric assay for urinary testosterone and dihydrotestosterone glucuronides from patients with benign prostate hyperplasia. Clin Chem. 2003 Feb;49(2):322-5. [PubMed:12560362 ]
  4. Farthing MJ, Rees LH, Edwards CR, Dawson AM: Male gonadal function in coeliac disease: 2. Sex hormones. Gut. 1983 Feb;24(2):127-35. [PubMed:6682819 ]
  5. Aganovic I, Alac M, Cabrijan T, Grizelj V, Korsic M, Misjak-Vitez M, Reiner Z, Suchanek E, Simunic V, Zjacic-Rotkvic V: [National consensus on hyperandrogenemia]. Lijec Vjesn. 1996 Sep;118(9):189-90. [PubMed:9011736 ]
  6. Clark RV, Hermann DJ, Cunningham GR, Wilson TH, Morrill BB, Hobbs S: Marked suppression of dihydrotestosterone in men with benign prostatic hyperplasia by dutasteride, a dual 5alpha-reductase inhibitor. J Clin Endocrinol Metab. 2004 May;89(5):2179-84. [PubMed:15126539 ]
  7. Sato T, Sonoda T, Itami S, Takayasu S: Predominance of type I 5alpha-reductase in apocrine sweat glands of patients with excessive or abnormal odour derived from apocrine sweat (osmidrosis). Br J Dermatol. 1998 Nov;139(5):806-10. [PubMed:9892945 ]
  8. Christiansen K, Knussmann R: Androgen levels and components of aggressive behavior in men. Horm Behav. 1987 Jun;21(2):170-80. [PubMed:3610056 ]
  9. Hammond GL, Leinonen P, Bolton NJ, Vihko R: Measurement of sex hormone binding globulin in human amniotic fluid: its relationship to protein and testosterone concentrations, and fetal sex. Clin Endocrinol (Oxf). 1983 Apr;18(4):377-84. [PubMed:6683603 ]
  10. Boccon-Gibod L, Laudat MH, Guiban D, Steg A: Hormonal consequences of orchidectomy for carcinoma of the prostate. With special reference to the measurement of free testosterone in saliva and prostatic dihydrotestosterone levels. Eur Urol. 1988;15(1-2):99-102. [PubMed:3215246 ]
  11. Misao R, Itoh N, Mori H, Fujimoto J, Tamaya T: Sex hormone-binding globulin mRNA levels in human uterine endometrium. Eur J Endocrinol. 1994 Dec;131(6):623-9. [PubMed:7804446 ]
  12. Toscano V, Horton R: Circulating dihydrotestosterone may not reflect peripheral formation. J Clin Invest. 1987 Jun;79(6):1653-8. [PubMed:3584464 ]
  13. Pineiro V, Casabiell X, Peino R, Lage M, Camina JP, Menendez C, Baltar J, Dieguez C, Casanueva F: Dihydrotestosterone, stanozolol, androstenedione and dehydroepiandrosterone sulphate inhibit leptin secretion in female but not in male samples of omental adipose tissue in vitro: lack of effect of testosterone. J Endocrinol. 1999 Mar;160(3):425-32. [PubMed:10076188 ]
  14. Dawood MY, Saxena BB: Testosterone and dihydrotestosterone in maternal and cord blood and in amniotic fluid. Am J Obstet Gynecol. 1977 Sep 1;129(1):37-42. [PubMed:900166 ]
  15. Geller J, Candari CD: Comparison of dihydrotestosterone levels in prostatic cancer metastases and primary prostate cancer. Prostate. 1989;15(2):171-5. [PubMed:2798234 ]
  16. Cutolo M, Seriolo B, Villaggio B, Pizzorni C, Craviotto C, Sulli A: Androgens and estrogens modulate the immune and inflammatory responses in rheumatoid arthritis. Ann N Y Acad Sci. 2002 Jun;966:131-42. [PubMed:12114267 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
Reactions
Dihydrotestosterone + NADPH + Hydrogen Ion → Androstan-3alpha,17beta-diol + NADPdetails
General function:
Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:
Converts testosterone (T) into 5-alpha-dihydrotestosterone (DHT) and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A2
Uniprot ID:
P31213
Molecular weight:
28407.035
Reactions
Dihydrotestosterone + Acceptor → Testosterone + Reduced acceptordetails
General function:
Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A1
Uniprot ID:
P18405
Molecular weight:
29458.18
Reactions
Dihydrotestosterone + Acceptor → Testosterone + Reduced acceptordetails
General function:
Involved in DNA binding
Specific function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:
AR
Uniprot ID:
P10275
Molecular weight:
98987.9
General function:
Involved in oxidoreductase activity, acting on the CH-CH group of donors
Specific function:
Plays a key role in early steps of protein N-linked glycosylation by being required for the conversion of polyprenol into dolichol. Dolichols are required for the synthesis of dolichol-linked monosaccharides and the oligosaccharide precursor used for N-glycosylation. Acts as a polyprenol reductase that promotes the reduction of the alpha-isoprene unit of polyprenols into dolichols in a NADP-dependent mechanism. Also able to convert testosterone (T) into 5-alpha-dihydrotestosterone (DHT).
Gene Name:
SRD5A3
Uniprot ID:
Q9H8P0
Molecular weight:
36521.005
Reactions
Dihydrotestosterone + Acceptor → Testosterone + Reduced acceptordetails