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Showing Compound Dihydrotestosterone (FDB023086)

Record Information
Version1.0
Creation date2011-09-21 00:24:28 UTC
Update date2024-11-29 22:28:05 UTC
Primary IDFDB023086
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDihydrotestosterone
DescriptionA 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 [HMDB]
CAS Number521-18-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
17beta-hydroxy-5alpha-androstan-3-onehmdb
17β-hydroxy-5α-androstan-3-oneGenerator
17β-hydroxyandrostan-3-oneGenerator
4,5α-dihydrotestosteroneGenerator
5A-Androstan-3-on-17B-olhmdb
5alpha-androstan-17beta-ol-3-onehmdb
5B-Androstan-3-on-17B-olhmdb
5α-dhtGenerator
5α-dihydrotestosteroneGenerator
Dihydrotestosteronehmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H30O2
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
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
Isomeric 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
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
Classification
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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000x-9870000000-f6d80b2a53942c9af50b2014-09-20View Spectrum
GC-MSDihydrotestosterone, non-derivatized, GC-MS Spectrumsplash10-015c-8970000000-ef0c6a4fd9c52be30284Spectrum
GC-MSDihydrotestosterone, non-derivatized, GC-MS Spectrumsplash10-001l-1790000000-60cff73adc796876d469Spectrum
GC-MSDihydrotestosterone, non-derivatized, GC-MS Spectrumsplash10-015c-8970000000-ef0c6a4fd9c52be30284Spectrum
GC-MSDihydrotestosterone, non-derivatized, GC-MS Spectrumsplash10-001l-1790000000-60cff73adc796876d469Spectrum
Predicted GC-MSDihydrotestosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03gj-0390000000-9eeab8ff981af1be878cSpectrum
Predicted GC-MSDihydrotestosterone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001j-2129000000-dbb4c264166c851e22c1Spectrum
Predicted GC-MSDihydrotestosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDihydrotestosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0bta-0930000000-078d7455103eab0cf1ee2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-08gj-0900000000-9f326ea5c1c454997fd32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0390000000-85c48da18cebca66ba3c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-f81b1315d55db1d47ec42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-02cv-0900000000-9d78808dd524e4ca6c502021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0bta-0930000000-49751ee4f183943f62fa2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0190000000-32b12edcbd16045a4a2e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0390000000-a2704bedea3c7bf92d652016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-2790000000-d1a3cc2c786b582339b32016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-62e8fc46490b14aee68a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-d712d8c85325f4935c062016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-2190000000-d8e9f38bc70955a04aea2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-48f400d66433b81d9a662021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aba-1950000000-acfc6238e1a13c48e8592021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066s-2900000000-1bc41566c7dc5d14c9032021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-20b22a4e3152e3639e642021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Spectrum
ChemSpider ID10189
ChEMBL IDCHEMBL27769
KEGG Compound IDC03917
Pubchem Compound ID10635
Pubchem Substance IDNot Available
ChEBI ID16330
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02961
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID42776
KNApSAcK IDNot Available
HET IDDHT
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDihydrotestosterone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
3-oxo-5-alpha-steroid 4-dehydrogenase 2SRD5A2P31213
3-oxo-5-alpha-steroid 4-dehydrogenase 1SRD5A1P18405
Androgen receptorARP10275
Polyprenol reductaseSRD5A3Q9H8P0
Pathways
NameSMPDB LinkKEGG Link
Androgen and Estrogen MetabolismSMP00068 map00150
Metabolism and Physiological Effects of Androsterone sulfateSMP0127012 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference