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Record Information
Version3.6
Creation Date2006-05-22 15:12:22 UTC
Update Date2016-02-11 01:05:55 UTC
HMDB IDHMDB02961
Secondary Accession NumbersNone
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. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
17beta-Hydroxy-3-oxo-5alpha-androstanoneChEBI
17beta-Hydroxyandrostan-3-oneChEBI
4,5alpha-DihydrotestosteroneChEBI
5alpha-DHTChEBI
5alpha-DihydrotestosteroneChEBI
AndrostanolonaChEBI
AndrostanoloneChEBI
AndrostanolonumChEBI
DHTChEBI
DihydrotestosteronChEBI
DIHYDROTESTOSTERONEChEBI
StanoloneChEBI
17b-Hydroxy-3-oxo-5a-androstanoneGenerator
17β-hydroxy-3-oxo-5α-androstanoneGenerator
17b-Hydroxyandrostan-3-oneGenerator
17β-hydroxyandrostan-3-oneGenerator
4,5a-DihydrotestosteroneGenerator
4,5α-dihydrotestosteroneGenerator
5a-DHTGenerator
5α-DHTGenerator
5a-DihydrotestosteroneGenerator
5α-dihydrotestosteroneGenerator
17-Hydroxy-androstan-3-oneHMDB
17-Hydroxyandrostan-3-oneHMDB
17b-Hydroxy-3-androstanoneHMDB
17beta-Hydroxy-5alpha-androstan-3-oneHMDB
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
AndractimHMDB
AndroloneHMDB
AndrostaloneHMDB
Cristerona MBHMDB
DrolbanHMDB
NeodrolHMDB
ProteinaHMDB
ProtonaHMDB
StanaprolHMDB
StanoroneHMDB
Chemical FormulaC19H30O2
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
IUPAC Name(1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
Traditional Namedihydrotestosterone
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 KeyInChIKey=NVKAWKQGWWIWPM-ABEVXSGRSA-N
Chemical Taxonomy
DescriptionThis compound 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-oxo-5-alpha-steroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • Cyclohexanone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point181 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility525 mg/mL at 25 °CNot Available
LogP3.55HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.01 mg/mLALOGPS
logP3.37ALOGPS
logP3.41ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.6 m3·mol-1ChemAxon
Polarizability34.69 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-000x-9870000000-f6d80b2a53942c9af50bView in MoNA
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Fibroblasts
  • Gonads
  • Hair
  • Kidney
  • Liver
  • Muscle
  • Myelin
  • Neuron
  • Prostate
  • Skin
  • Testes
  • Thyroid Gland
Pathways
NameSMPDB LinkKEGG Link
Androgen and Estrogen MetabolismSMP00068map00150
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00041 +/- 0.00016 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0054 +/- 0.0028 uMAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0054 +/- 0.0029 uMAdult (>18 years old)Both
Psychiatric disorder
details
Cerebrospinal Fluid (CSF)Detected and Quantified1.0000e-06 +/- 4.135e-06 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism details
Cerebrospinal Fluid (CSF)Detected and Quantified1.275e-05 +/- 1.792e-05 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. [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. [16959481 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00558
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023086
KNApSAcK IDNot Available
Chemspider ID10189
KEGG Compound IDC03917
BioCyc ID17-BETA-HYDROXY-5ALPHA-ANDROSTAN-3-O
BiGG ID42776
Wikipedia LinkDihydrotestosterone
NuGOwiki LinkHMDB02961
Metagene LinkHMDB02961
METLIN ID2789
PubChem Compound10635
PDB IDDHT
ChEBI ID16330
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. [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. [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. [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. [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. [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. [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. [9892945 ]
  8. Christiansen K, Knussmann R: Androgen levels and components of aggressive behavior in men. Horm Behav. 1987 Jun;21(2):170-80. [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. [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. [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. [7804446 ]
  12. Toscano V, Horton R: Circulating dihydrotestosterone may not reflect peripheral formation. J Clin Invest. 1987 Jun;79(6):1653-8. [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. [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. [900166 ]
  15. Geller J, Candari CD: Comparison of dihydrotestosterone levels in prostatic cancer metastases and primary prostate cancer. Prostate. 1989;15(2):171-5. [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. [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