Showing Metabocard for 17beta-hydroxy-5alpha-androstan-3-one (BASm0000589)

Common Name17beta-hydroxy-5alpha-androstan-3-one
DescriptionDihydrotestosterone 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.
Structure
Molecular FormulaC19H30O2
Average Mass290.44030
Monoisotopic Mass290.22458
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
Traditional NameDihydrotestosterone
CAS Registry Number521-18-6
SMILESC[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
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
CHEBI IDCHEBI:16330
HMDB IDHMDB0002961
Pathways
NameSMPDB/PathBank
Androgen and Estrogen Metabolism
StateNot Available
Water Solubility9.98e-03 g/l
logP3.37
logS-4.46
pKa (Strongest Acidic)19.38
pKa (Strongest Basic)-0.88
Hydrogen Acceptor Count2
Hydrogen Donor Count1
Polar Surface Area37.3 Ų
Rotatable Bond Count0
Physiological Charge0
Formal Charge0
Refractivity83.60 m³·mol⁻¹
Polarizability34.69

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