3β-Dihydroprogesterone

3β-Dihydroprogesterone
Names
	IUPAC name 3β-Hydroxypregn-4-en-20-one
	Systematic IUPAC name 1-[(1S,3aS,3bS,7S,9aR,9bS,11aS)-7-Hydroxy-9a,11a-dimethyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one
	Other names Pregn-4-en-3β-ol-20-one; 3β-Dihydroprogesterone; 3β-DHP; δ4-Pregnenolone; 4-Pregnenolone
Identifiers
CAS Number	566-66-5;
3D model (JSmol)	Interactive image;
ChemSpider	19148924;
PubChem CID	12838303;
UNII	AW2D4ZZ5YQ ;
	InChI InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,15-19,23H,4-11H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1 Key: QWVWXRKHAXWWSV-QGVNFLHTSA-N;
	SMILES CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C[C@H](CC[C@]34C)O)C;
Properties
Chemical formula	C21H32O2
Molar mass	316.485 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3β-Dihydroprogesterone (3β-DHP), also known as 3β-hydroxyprogesterone, or pregn-4-en-3β-ol-20-one (4-pregnenolone, δ⁴-pregnenolone), is an endogenous steroid. It is biosynthesized by 3β-hydroxysteroid dehydrogenase from progesterone. Unlike 3α-dihydroprogesterone (3α-DHP), 3β-DHP does not act as a positive allosteric modulator of the GABA_A receptor, which is in accordance with the fact that other 3β-hydroxylated progesterone metabolites such as isopregnanolone and epipregnanolone similarly do not act as potentiators of this receptor and instead inhibit it as well as reverse the effects of potentiators like allopregnanolone. 3β-DHP has been reported to possess about the same potency as progesterone in a bioassay of progestogenic activity, whereas 3α-DHP was not assessed.

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