Record Information |
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Version | 2.0 |
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Creation Date | 2014-09-11 05:14:48 UTC |
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Update Date | 2014-12-24 20:26:56 UTC |
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Accession Number | T3D4751 |
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Identification |
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Common Name | Dihydrotestosterone |
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Class | Small Molecule |
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Description | Dihydrotestosterone 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. |
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Compound Type | - Androgen
- Animal Toxin
- Drug
- Food Toxin
- Metabolite
- Natural Compound
- Organic Compound
- Steroid
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Chemical Structure | |
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Synonyms | Synonym | (5a,17b)-17-Hydroxyandrostan-3-one | (5alpha,17beta)-17-hydroxyandrostan-3-one | 17-Hydroxy-androstan-3-one | 17-Hydroxyandrostan-3-one | 17b-Hydroxy-3-androstanone | 17beta-hydroxy-5alpha-androstan-3-one | 17beta-Hydroxy-5alpha-androstane-3-one | 17beta-Hydroxyandrostan-3-one | 4,5a-Dihydrotestosterone | 4-Dihydrotestosterone | 5-a-Androstanolone | 5-alpha-Androstanolone | 5.alpha.-Dihydrotestosterone | 5a-Androstan-17b-ol-3-one | 5A-Androstan-3-on-17B-ol | 5a-Dihydrotestosterone | 5alpha dihydrotestosterone | 5alpha-androstan-17beta-ol-3-one | 5alpha-Dihydrotestosterone | 5B-Androstan-3-on-17B-ol | Anaboleen | Anabolex | Anaprotin | Andractim | Androlone | Androstalone | Androstan-17b-ol-3-one | Androstan-17beta-ol-3-one | Androstanolone | Cristerona MB | DHT | Drolban | Neodrol | Proteina | Protona | Stanaprol | Stanolone | Stanorone |
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Chemical Formula | C19H30O2 |
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Average Molecular Mass | 290.440 g/mol |
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Monoisotopic Mass | 290.225 g/mol |
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CAS Registry Number | 521-18-6 |
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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 |
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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 |
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SMILES | [H][C@]1(O)CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C |
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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 |
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InChI Key | InChIKey=NVKAWKQGWWIWPM-ABEVXSGRSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Androstane steroids |
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Direct Parent | Androgens and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Endogenous |
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Cellular Locations | - Cytoplasm
- Endoplasmic reticulum
- Extracellular
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | - Adipose Tissue
- Adrenal Cortex
- Adrenal Gland
- Fibroblasts
- Gonads
- Hair
- Kidney
- Liver
- Muscle
- Myelin
- Neuron
- Prostate
- Skin
- Testes
- Thyroid Gland
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Pathways | |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 181°C | Boiling Point | Not Available | Solubility | 525 mg/mL at 25°C | LogP | 3.55 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-015c-8970000000-ef0c6a4fd9c52be30284 | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-001l-1790000000-60cff73adc796876d469 | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-015c-8970000000-ef0c6a4fd9c52be30284 | 2018-05-18 | View Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-001l-1790000000-60cff73adc796876d469 | 2018-05-18 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03gj-0390000000-9eeab8ff981af1be878c | 2017-09-01 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-001j-2129000000-dbb4c264166c851e22c1 | 2017-10-06 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0bta-0930000000-078d7455103eab0cf1ee | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-08gj-0900000000-9f326ea5c1c454997fd3 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-0390000000-85c48da18cebca66ba3c | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0090000000-f81b1315d55db1d47ec4 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-02cv-0900000000-9d78808dd524e4ca6c50 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0bta-0930000000-49751ee4f183943f62fa | 2021-09-20 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dl-0190000000-32b12edcbd16045a4a2e | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dl-0390000000-a2704bedea3c7bf92d65 | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-016r-2790000000-d1a3cc2c786b582339b3 | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-62e8fc46490b14aee68a | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0090000000-d712d8c85325f4935c06 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05fu-2190000000-d8e9f38bc70955a04aea | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0090000000-48f400d66433b81d9a66 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0aba-1950000000-acfc6238e1a13c48e859 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-066s-2900000000-1bc41566c7dc5d14c903 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-c8c452fd99c6bb4f3631 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0090000000-c8c452fd99c6bb4f3631 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-0090000000-20b22a4e3152e3639e64 | 2021-09-22 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-000x-9870000000-f6d80b2a53942c9af50b | 2014-09-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental) | Not Available | 2014-09-23 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Bioavailability is very low (0-2%) following oral administration. |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Dihydrotestosterone is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB02901 |
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HMDB ID | HMDB02961 |
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PubChem Compound ID | 10635 |
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ChEMBL ID | Not Available |
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ChemSpider ID | 14 |
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KEGG ID | C03917 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 16330 |
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BioCyc ID | 17-BETA-HYDROXY-5ALPHA-ANDROSTAN-3-O |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | DHT |
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ACToR ID | Not Available |
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Wikipedia Link | Dihydrotestosterone |
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References |
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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. |
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MSDS | Link |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Christiansen K, Knussmann R: Androgen levels and components of aggressive behavior in men. Horm Behav. 1987 Jun;21(2):170-80. [3610056 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Toscano V, Horton R: Circulating dihydrotestosterone may not reflect peripheral formation. J Clin Invest. 1987 Jun;79(6):1653-8. [3584464 ]
- 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 ]
- 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 ]
- Geller J, Candari CD: Comparison of dihydrotestosterone levels in prostatic cancer metastases and primary prostate cancer. Prostate. 1989;15(2):171-5. [2798234 ]
- 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 ]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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