LIPID MAPS

11-deoxy Corticosterone (DOC) is an endogenous mineralocorticoid synthesized in the zona fasciculata and zona glomerulosa of the adrenal gland.¹ It is a metabolite of progesterone and precursor to aldosterone and corticosterone .² DOC is metabolized to the neuroactive compound (3α,5α)-2,21-dihydroxypregnan-20-one (THDOC), which positively modulates GABAA receptors and produces effects similar to barbiturates in rats.³ Injections of naloxone (ISO60191) and corticotropin-releasing hormone (CRH) increase, while dexamethasone decreases, DOC in cynomolgus monkeys.¹ DOC levels are increased 3.4-fold in obese and diabetic mice.²

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References

1. Hofmann, A., Peitzsch, M., Brunssen, C., et al. Elevated steroid hormone production in the db/db mouse model of obesity and type 2 diabetes. Horm. Metab. Res. 49(1), 43-49 (2017).

2. Jimenez, V.A., Porcu, P., Morrow, A.L., et al. Adaptations in basal and hypothalamic-pituitary-adrenal-activated deoxycorticosterone responses following ethanol self-administration in cynomolgus monkeys. Front. Endocrinol. (Lausanne) 8(19), (2017).

3. Majewska, M.D., Harrison, N.L., Schwartz, R.D., et al. Steroid hormone metabolites are barbiturate-like modulators of the GABA receptor. Science 232(4753), 1004-1007 (1986).

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String Representations

InChiKey (Click to copy)

ZESRJSPZRDMNHY-YFWFAHHUSA-N

InChi (Click to copy)

InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1

SMILES (Click to copy)

[C@]12(CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@H](C(=O)CO)CC[C@@]21[H])[H]