5α-Pregnane-3α,17α-diol-20-one
Chemical compound
From Wikipedia, the free encyclopedia
5α-Pregnane-3α,17α-diol-20-one, also known as 17α-hydroxyallopregnanolone (17-OH-allo) is an endogenous steroid.
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| 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 | |
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| 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).
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Function
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]
Biosynthesis
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]