5b-Dihydrotestosterone (CHEM036233)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:20:02 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036233
Identification
Common Name5b-Dihydrotestosterone
ClassSmall Molecule
Description5b-Dihydrotestosterone, also known as 5-beta-DHT or 5-β-DHT, 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. Thus, 5b-dihydrotestosterone is considered to be a steroid lipid molecule. 5b-Dihydrotestosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5b-Dihydrotestosterone can be converted into testosterone through its interaction with the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. In cattle, 5b-dihydrotestosterone is involved in the metabolic pathway called the androgen and estrogen metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(5beta,17beta)-17-Hydroxyandrostan-3-oneChEBI
(5beta,8alpha,17beta)-17-Hydroxyandrostan-3-oneChEBI
17beta-Hydroxyetiocholan-3-oneChEBI
5-beta-DHTChEBI
5beta,17beta-Hydroxyandrostan-3-oneChEBI
5beta-Androstan-17beta-ol-3-oneChEBI
Etiocholan-17-beta-ol-3-oneChEBI
(5b,17b)-17-Hydroxyandrostan-3-oneGenerator
(5Β,17β)-17-hydroxyandrostan-3-oneGenerator
(5b,8a,17b)-17-Hydroxyandrostan-3-oneGenerator
(5Β,8α,17β)-17-hydroxyandrostan-3-oneGenerator
17b-Hydroxyetiocholan-3-oneGenerator
17Β-hydroxyetiocholan-3-oneGenerator
5-b-DHTGenerator
5-Β-DHTGenerator
5b,17b-Hydroxyandrostan-3-oneGenerator
5Β,17β-hydroxyandrostan-3-oneGenerator
5b-Androstan-17b-ol-3-oneGenerator
5Β-androstan-17β-ol-3-oneGenerator
Etiocholan-17-b-ol-3-oneGenerator
Etiocholan-17-β-ol-3-oneGenerator
5beta-DihydrotestosteroneHMDB
17beta-Hydroxy-5beta-androstan-3-oneHMDB
Chemical FormulaC19H30O2
Average Molecular Mass290.440 g/mol
Monoisotopic Mass290.225 g/mol
CAS Registry Number571-22-2
IUPAC Name(1S,2S,7R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
Traditional Name5β-dihydrotestosterone
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+/m1/s1
InChI KeyNVKAWKQGWWIWPM-MISPCMORSA-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-beta-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
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability34.46 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gj-0390000000-9eeab8ff981af1be878cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-007k-2249000000-51ef016e7481976493bdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-62e8fc46490b14aee68aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-d712d8c85325f4935c06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-2190000000-d8e9f38bc70955a04aeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-c8c452fd99c6bb4f3631Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-c8c452fd99c6bb4f3631Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-20b22a4e3152e3639e64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0190000000-32b12edcbd16045a4a2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0390000000-a2704bedea3c7bf92d65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-2790000000-d1a3cc2c786b582339b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-48f400d66433b81d9a66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aba-1950000000-acfc6238e1a13c48e859Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066s-2900000000-1bc41566c7dc5d14c903Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB07447
HMDB IDHMDB0006770
FooDB IDFDB024072
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID10827
ChEBI ID428206
PubChem Compound ID11302
Kegg Compound IDC05293
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10357254
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11430920
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15758151
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17804019
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18276759
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19215525
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=591837
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=6542571