5β-Dihydrotestosterone

5β-Dihydrotestosterone
Names
	IUPAC name 17β-Hydroxy-5β-androstan-3-one
	Systematic IUPAC name (1S,3aS,3bR,5aR,9aS,9bS,11aS)-1-Hydroxy-9a,11a-dimethylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one
	Other names 5β-Androstan-17β-ol-3-one; Etiocholan-17β-ol-3-one; 5β-Dihydrotestosterone; 5β-DHT
Identifiers
CAS Number	571-22-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:2150;
ChEMBL	ChEMBL373357;
ChemSpider	10827;
DrugBank	DB07447;
ECHA InfoCard	100.164.933
EC Number	637-207-6;
KEGG	C05293;
PubChem CID	11302;
UNII	SVX1G0C5VD ;
CompTox Dashboard (EPA)	DTXSID0022488 ;
	InChI 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 Key: NVKAWKQGWWIWPM-MISPCMORSA-N;
	SMILES C[C@]12CCC(=O)C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C;
Properties
Chemical formula	C19H30O2
Molar mass	290.447 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H312, H332, H350, H360
Precautionary statements	P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

5β-Dihydrotestosterone (5β-DHT), also known as 5β-androstan-17β-ol-3-one or as etiocholan-17β-ol-3-one, is an etiocholane (5β-androstane) steroid as well as an inactive metabolite of testosterone formed by 5β-reductase in the liver and bone marrow^[1]^[2] and an intermediate in the formation of 3α,5β-androstanediol and 3β,5β-androstanediol (by 3α- and 3β-hydroxysteroid dehydrogenase) and, from them, respectively, etiocholanolone and epietiocholanolone (by 17β-hydroxysteroid dehydrogenase).^[3]^[4] Unlike its isomer 5α-dihydrotestosterone (5α-DHT or simply DHT), 5β-DHT either does not bind to or binds only very weakly to the androgen receptor.^[1] 5β-DHT is notable among metabolites of testosterone in that, due to the fusion of the A and B rings in the cis orientation, it has an extremely angular molecular shape, and this could be related to its lack of androgenic activity.^[5] 5β-DHT, unlike 5α-DHT, is also inactive in terms of neurosteroid activity,^[6]^[7] although its metabolite, etiocholanolone, does possess such activity.^[8]^[9]

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