4299 Deoxycorticosterone 11-Deoxycorticosterone (also called desoxycortone, 21-hydroxyprogesterone, DOC, or simply deoxycorticosterone) is a steroid hormone produced by the adrenal gland that possesses mineralocorticoid activity and acts as a precursor to aldosterone. It is classified as a member of the 21-hydroxysteroids. 21-hydroxysteroids are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Deoxycorticosterone is very hydrophobic, practically insoluble (in water), and relatively neutral. Deoxycorticosterone can be synthesized from progesterone by 21-beta-hydroxylase and is then converted to corticosterone by 11-beta-hydroxylase. Corticosterone is then converted to aldosterone by aldosterone synthase. Deoxycorticosterone can be found throughout all human tissues and has been detected in amniotic fluid and blood. When present in sufficiently high levels, deoxycorticosterone can act as a hypertensive agent and a metabotoxin. A hypertensive agent increases blood pressure and causes the production of more urine. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of deoxycorticosterone are associated with congenital adrenal hyperplasia (CAH) and with adrenal tumors producing deoxycorticosterone (PMID: 20671982). High levels of this mineralocorticoid are associated with resistant hypertension, which can result in polyuria, polydipsia, increased blood volume, edema, and cardiac enlargement. 64-85-7 6166 C21H30O3 White powder. 141 - 142°C 0.0595 mg/mL at 37°C No indication of carcinogenicity to humans (not listed by IARC). This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation. Chronically high levels of deoxycorticosterone are associated with the inborn errors of metabolism known as Congenital adrenal hyperplasia. 2014-08-29T06:02:24Z 2018-03-21T17:46:11Z Deoxycorticosterone C03205 16973 11-DEOXYCORTICOSTERONE 1CA true [H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(=O)CO C21H30O3 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 InChIKey=ZESRJSPZRDMNHY-YFWFAHHUSA-N 330.4611 330.219494826 Endogenous Solid 2.88 HMDB00016 CHEMBL1498 5932 Mattox V R; Goodrich J E; Vrieze W D Synthesis of C-21 glucosiduronates of cortisone and related corticosteroids. Biochemistry (1969), 8(3), 1188-99.