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Record Information
Version3.6
Creation Date2008-08-06 16:25:44 UTC
Update Date2016-02-11 01:07:56 UTC
HMDB IDHMDB06770
Secondary Accession NumbersNone
Metabolite Identification
Common Name5b-Dihydrotestosterone
Description5beta-Dihydrotestosterone is an intermediate in Androgen and estrogen metabolism. 5beta-Dihydrotestosterone is generated from Testosterone via the enzyme 3-oxo-5beta-steroid 4-dehydrogenase (EC 1.3.99.6).
Structure
Thumb
Synonyms
ValueSource
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 KeyInChIKey=NVKAWKQGWWIWPM-MISPCMORSA-N
Chemical Taxonomy
DescriptionThis compound 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.01 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.6 m3·mol-1ChemAxon
Polarizability34.46 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
17-Beta Hydroxysteroid Dehydrogenase III DeficiencySMP00356Not Available
Androgen and Estrogen MetabolismSMP00068map00150
Aromatase deficiencySMP00565Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024072
KNApSAcK IDNot Available
Chemspider ID10827
KEGG Compound IDC05293
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06770
Metagene LinkHMDB06770
METLIN IDNot Available
PubChem Compound11302
PDB IDBDT
ChEBI ID428206
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