![]() | |
Names | |
---|---|
IUPAC name 3α,17-Dihydroxy-5α-pregnan-20-one [1] | |
Systematic IUPAC name 1-[(1R,3aS,3bR,5aS,7R,9aS,9bS,11aS)-1,7-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one | |
Other names | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
EC Number |
|
PubChem CID | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C21H34O3 | |
Molar mass | 334.500 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
5α-Pregnane-3α,17α-diol-20-one, also known as 17α-hydroxyallopregnanolone (17-OH-allo) is an endogenous steroid.
5α-Pregnane-3α,17α-diol-20-one is a metabolite, an intermediate product within the androgen backdoor pathway [17] in which 17α-hydroxyprogesterone (17-OHP) is 5α-reduced and finally converted to 5α-dihydrotestosterone (DHT) without testosterone as a metabolic intermediate. [18] [6]
The pathway can be outlined as 17-OHP → 5α-pregnan-17α-ol-3,20-dione → 5α-pregnane-3α,17α-diol-20-one → androsterone → 5α-androstane-3α,17β-diol → DHT. [19] [14] [20]
5α-Pregnane-3α,17α-diol-20-one is produced from 5α-pregnan-17α-ol-3,20-dione [21] in a reaction catalyzed by a reductive 3α-hydroxysteroid dehydrogenase (3α-HSD), [22] i.e. by the two aldo-keto reductase isozymes: AKR1C2 and AKR1C4, [23] and by 17β-hydroxysteroid dehydrogenase 6 (HSD17B6) that also has the 3α-HSD activity. [23]
Most steroids are identified by their common names; 17-hydroxy-dihydroprogesterone (17OH-DHP) is 5α-pregnane-17α-ol-3,20-dione; 17-hydroxy-allopregnanolone (17OH-allo) is 5α-pregnan-3α,17α-diol-20-one; 5α-dihydroprogesterone (5α-DHP) is 5α-pregnane-3,20-dione, and allopregnanolone is 3α-hydroxy-dihydroprogesterone (3α-OH-DHP) or 5α-pregnane-3α-ol-20-one.
17-OH-Allo 5α-pregnane-3α,17α-diol-20-one (17-hydroxyallopregnanolone)
17-Hydroxyallopregnanolone, Metabolite, CHEBI:11909 (ChEBI)
17-hydroxyallopregnanolone (5-pregnane-3,17-diol-20-one)
The product of 17-hydroxyprogesterone reduction, 5α-pregnan-17α-ol-3,20-dione, was metabolized by a reductive 3α-HSD to a new key intermediate, 5α-pregnane-3α,17α-diol-20-one (Pdiol)