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17α-hydroxy Pregnenolone is a metabolite of pregnenolone and a precursor in the biosynthesis of dehydroepiandrosterone (DHEA).¹ It is formed from pregnenolone by cytochrome P450 (CYP) isoform CYP17A1 hydroxylase activity and then converted to dehydroepiandrosterone by CYP17A1-mediated 17,20-lyase activity. Plasma levels of 17α-hydroxy pregnenolone are elevated in patients with type II 3β-hydroxysteroid dehydrogenase deficiency, a form of congenital adrenal hyperplasia.²

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References

1. Petrunak, E.M., DeVore, N.M., Porubsky, P.R., et al. Structures of human steroidogenic cytochrome P450 17A1 with substrates. The Journal of Biological Chemisty 289(47), 32952-32964 (2014).

2. Fiet, J., Giton, F., Boudi, A., et al. Plasma 17-OH pregnenolone: Comparison of a time-resolved fluoroimmunoassay using a new tracer 17-OH pregnenolone-3-oxyacetyl-biotine with a radioimmunoassay using 125I 17-OH pregnenolone-3-hemisuccinate-histamine. Steroids 66(2), 81-86 (2001).

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String Representations

InChiKey (Click to copy)

JERGUCIJOXJXHF-TVWVXWENSA-N

InChi (Click to copy)

InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1

SMILES (Click to copy)

[C@]12(CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@](O)(C(=O)C)CC[C@@]21[H])[H]