Comparison of chemical structures for
allopregnane,
allopregnanolone and 5α-Pregnane-3α,17α-diol-20-one (17α-allopregnanolone). Please note that the difference between the
allopregnanolone and 5α-Pregnane-3α,17α-diol-20-one is a hydroxyl function group (−OH) at C17 position.Structure of
cholestane, a steroid with 27 carbon atoms. Its core ring system (ABCD), composed of 17 carbon atoms, is shown with
IUPAC-approved ring lettering and atom numbering.
5α-Pregnane-3α,17α-diol-20-one, also known as 17α-hydroxyallopregnanolone (17-OH-allo) is an
endogenoussteroid.
^Barnard L, Gent R, van Rooyen D, Swart AC (November 2017). "Adrenal C11-oxy C21 steroids contribute to the C11-oxy C19 steroid pool via the backdoor pathway in the biosynthesis and metabolism of 21-deoxycortisol and 21-deoxycortisone". The Journal of Steroid Biochemistry and Molecular Biology. 174: 86–95.
doi:
10.1016/j.jsbmb.2017.07.034.
PMID28774496.
S2CID24071400.
^Bremer AA, Miller WL (2014).
"Regulation of Steroidogenesis". Cellular Endocrinology in Health and Disease. Academic Press. pp. 207–227.
doi:
10.1016/B978-0-12-408134-5.00013-5.
ISBN978-0-12-408134-5.
Archived from the original on 24 October 2020. Retrieved 21 October 2020. 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.
^
abGupta MK, Guryev OL, Auchus RJ (October 2003). "5alpha-reduced C21 steroids are substrates for human cytochrome P450c17". Archives of Biochemistry and Biophysics. 418 (2): 151–160.
doi:
10.1016/j.abb.2003.07.003.
PMID14522586.
^Saito K, Matsuzaki T, Iwasa T, Miyado M, Saito H, Hasegawa T, et al. (April 2016). "Steroidogenic pathways involved in androgen biosynthesis in eumenorrheic women and patients with polycystic ovary syndrome". The Journal of Steroid Biochemistry and Molecular Biology. 158: 31–37.
doi:
10.1016/j.jsbmb.2016.02.010.
PMID26877255.
S2CID22243788.
Comparison of chemical structures for
allopregnane,
allopregnanolone and 5α-Pregnane-3α,17α-diol-20-one (17α-allopregnanolone). Please note that the difference between the
allopregnanolone and 5α-Pregnane-3α,17α-diol-20-one is a hydroxyl function group (−OH) at C17 position.Structure of
cholestane, a steroid with 27 carbon atoms. Its core ring system (ABCD), composed of 17 carbon atoms, is shown with
IUPAC-approved ring lettering and atom numbering.
5α-Pregnane-3α,17α-diol-20-one, also known as 17α-hydroxyallopregnanolone (17-OH-allo) is an
endogenoussteroid.
^Barnard L, Gent R, van Rooyen D, Swart AC (November 2017). "Adrenal C11-oxy C21 steroids contribute to the C11-oxy C19 steroid pool via the backdoor pathway in the biosynthesis and metabolism of 21-deoxycortisol and 21-deoxycortisone". The Journal of Steroid Biochemistry and Molecular Biology. 174: 86–95.
doi:
10.1016/j.jsbmb.2017.07.034.
PMID28774496.
S2CID24071400.
^Bremer AA, Miller WL (2014).
"Regulation of Steroidogenesis". Cellular Endocrinology in Health and Disease. Academic Press. pp. 207–227.
doi:
10.1016/B978-0-12-408134-5.00013-5.
ISBN978-0-12-408134-5.
Archived from the original on 24 October 2020. Retrieved 21 October 2020. 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.
^
abGupta MK, Guryev OL, Auchus RJ (October 2003). "5alpha-reduced C21 steroids are substrates for human cytochrome P450c17". Archives of Biochemistry and Biophysics. 418 (2): 151–160.
doi:
10.1016/j.abb.2003.07.003.
PMID14522586.
^Saito K, Matsuzaki T, Iwasa T, Miyado M, Saito H, Hasegawa T, et al. (April 2016). "Steroidogenic pathways involved in androgen biosynthesis in eumenorrheic women and patients with polycystic ovary syndrome". The Journal of Steroid Biochemistry and Molecular Biology. 158: 31–37.
doi:
10.1016/j.jsbmb.2016.02.010.
PMID26877255.
S2CID22243788.