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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-06 16:25:44 UTC
Update Date2021-09-14 15:40:23 UTC
HMDB IDHMDB0006770
Secondary Accession Numbers
  • HMDB06770
Metabolite Identification
Common Name5b-Dihydrotestosterone
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.
Structure
Data?1582752405
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 Weight290.4403
Monoisotopic Molecular Weight290.224580204
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
CAS Registry Number571-22-2
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+/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
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP10(3.37) g/LALOGPS
logP10(3.41) g/LChemAxon
logS10(-4.5) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+170.08231661259
DarkChem[M-H]-166.31531661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5b-Dihydrotestosterone,1TMS,#1C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2O[Si](C)(C)C2624.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
5b-Dihydrotestosterone,1TMS,#2C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]34C)[C@@H]1CC[C@@H]2O2596.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
5b-Dihydrotestosterone,1TMS,#3C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC[C@@H]2O2578.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
5b-Dihydrotestosterone,1TBDMS,#1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C2887.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
5b-Dihydrotestosterone,1TBDMS,#2CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3CC[C@]4(C)[C@@H](O)CC[C@H]4[C@@H]3CC[C@@H]2C12864.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
5b-Dihydrotestosterone,1TBDMS,#3CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC12823.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Dihydrotestosterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gj-0390000000-9eeab8ff981af1be878c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Dihydrotestosterone GC-MS (1 TMS) - 70eV, Positivesplash10-007k-2249000000-51ef016e7481976493bd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Dihydrotestosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Dihydrotestosterone 10V, Positive-QTOFsplash10-00dl-0190000000-32b12edcbd16045a4a2e2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Dihydrotestosterone 20V, Positive-QTOFsplash10-00dl-0390000000-a2704bedea3c7bf92d652017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Dihydrotestosterone 40V, Positive-QTOFsplash10-016r-2790000000-d1a3cc2c786b582339b32017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Dihydrotestosterone 10V, Negative-QTOFsplash10-000i-0090000000-62e8fc46490b14aee68a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Dihydrotestosterone 20V, Negative-QTOFsplash10-000i-0090000000-d712d8c85325f4935c062017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Dihydrotestosterone 40V, Negative-QTOFsplash10-05fu-2190000000-d8e9f38bc70955a04aea2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Dihydrotestosterone 10V, Positive-QTOFsplash10-0006-0090000000-48f400d66433b81d9a662021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Dihydrotestosterone 20V, Positive-QTOFsplash10-0aba-1950000000-acfc6238e1a13c48e8592021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Dihydrotestosterone 40V, Positive-QTOFsplash10-066s-2900000000-1bc41566c7dc5d14c9032021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Dihydrotestosterone 10V, Negative-QTOFsplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Dihydrotestosterone 20V, Negative-QTOFsplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Dihydrotestosterone 40V, Negative-QTOFsplash10-000i-0090000000-20b22a4e3152e3639e642021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07447
Phenol Explorer Compound IDNot Available
FooDB IDFDB024072
KNApSAcK IDNot Available
Chemspider ID10827
KEGG Compound IDC05293
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11302
PDB IDNot Available
ChEBI ID428206
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Reactions
5b-Dihydrotestosterone + NADP → Testosterone + NADPH + Hydrogen Iondetails