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Record Information
Version1.0
Creation Date2014-09-11 05:14:48 UTC
Update Date2016-11-09 01:09:12 UTC
Accession NumberCHEM003708
Identification
Common NameDihydrotestosterone
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Androgen
  • Animal Toxin
  • Drug
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Steroid
Chemical Structure
Thumb
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 Mass290.440 g/mol
Monoisotopic Mass290.225 g/mol
CAS Registry Number521-18-6
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
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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • 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 MetabolismSMP00068 map00150
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point181°C
Boiling PointNot Available
Solubility525 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.6 m³·mol⁻¹ChemAxon
Polarizability34.54 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-03gj-0390000000-9eeab8ff981af1be878cView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-015c-8970000000-ef0c6a4fd9c52be30284View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001l-1790000000-60cff73adc796876d469View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-001j-2129000000-dbb4c264166c851e22c1View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-015c-8970000000-ef0c6a4fd9c52be30284View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001l-1790000000-60cff73adc796876d469View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0190000000-32b12edcbd16045a4a2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0390000000-a2704bedea3c7bf92d65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-2790000000-d1a3cc2c786b582339b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-62e8fc46490b14aee68aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-d712d8c85325f4935c06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-2190000000-d8e9f38bc70955a04aeaView in MoNA
MSMass Spectrum (Electron Ionization)splash10-000x-9870000000-f6d80b2a53942c9af50bView in MoNA
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureBioavailability is very low (0-2%) following oral administration.
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesDihydrotestosterone is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02901
HMDB IDHMDB0002961
FooDB IDFDB023086
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID42776
BioCyc ID17-BETA-HYDROXY-5ALPHA-ANDROSTAN-3-O
METLIN ID2789
PDB IDNot Available
Wikipedia LinkDihydrotestosterone
Chemspider ID10189
ChEBI ID16330
PubChem Compound ID10635
Kegg Compound IDC03917
YMDB IDNot Available
ECMDB IDM2MDB005768
References
Synthesis Reference

A. Glenn Braswell, Aftab J. Ahmed, “Composition for inhibiting production of dihydrotestosterone to treat benign prostate hyperplasia.” U.S. Patent US6264996, issued October, 1996.

MSDSLink
General References
1. Gardi, Rinaldo; Castelli, Pier Paolo; Gandolfi, Roberto; Ercoli, Alberto. Conversion of 5a-pregnane-3,2O-dione to dihydrotestosterone. (1961), 1250-7.
2. Gardi, Rinaldo; Castelli, Pier Paolo; Gandolfi, Roberto; Ercoli, Alberto. Conversion of 5a-pregnane-3,2O-dione to dihydrotestosterone. (1961), 1250-7.
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.
4. 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.
5. Farthing MJ, Rees LH, Edwards CR, Dawson AM: Male gonadal function in coeliac disease: 2. Sex hormones. Gut. 1983 Feb;24(2):127-35.
6. 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.
7. 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.
8. 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.
9. Christiansen K, Knussmann R: Androgen levels and components of aggressive behavior in men. Horm Behav. 1987 Jun;21(2):170-80.
10. 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.
11. 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.
12. 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.
13. 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.
14. Toscano V, Horton R: Circulating dihydrotestosterone may not reflect peripheral formation. J Clin Invest. 1987 Jun;79(6):1653-8.
15. 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.
16. 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.
17. Geller J, Candari CD: Comparison of dihydrotestosterone levels in prostatic cancer metastases and primary prostate cancer. Prostate. 1989;15(2):171-5.
18. 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.
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=15251265
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=15811352
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=18076420