11-Deoxycorticosterone

Last modified: Fri Jul 9 14:29:24 BST 2004

Steroid carbon nomenclature

Trivial names: 11-Deoxycorticosterone; Deoxycorticosterone; 11-Desoxycorticosterone; Desoxycortone; DOC; 21-Hydroxyprogesterone; Kendall's desoxy compound B
Systematic name: 21-Hydroxypregn-4-ene-3,20-dione
Molecular formula: C21H30O3
CAS Number: 64-85-7
Merck Index (11th Ed) Number: 2882

Substrate [1]

Pathway: 11-Deoxycorticosterone -> Corticosterone
Reaction: steroid ß-hydroxylation at C11
Enzyme: P450c11 (steroid 11ß-hydroxylase), CYP11B
EC 1.14.15.4

Substrate [1]

Pathway: 11-Deoxycorticosterone -> 18-Hydroxydeoxycorticosterone
Reaction: steroid hydroxylation at C18
Enzyme: P450c18 (steroid 18-hydroxylase), CYP11B
EC 1.14.15.4 Enzyme: P450c18 (steroid 18-hydroxylase), CYP11B2
EC 1.14.15.5 Enzyme: P450c18 (steroid 18-hydroxylase), CYP11B3
EC 1.14.15.4

Substrate [1]

Pathway: 11-Deoxycorticosterone -> 19-Hydroxydeoxycorticosterone
Reaction: steroid hydroxylation at C19
Enzyme: P450c19 (steroid 19-hydroxylase), CYP11B
EC 1.14.15.4

Product

Pathway: Progesterone -> 11-Deoxycorticosterone
Reaction: steroid hydroxylation at C21
Enzyme: P450c21 (steroid 21-hydroxylase), CYP21A [1]
EC 1.14.99.10 Enzyme: progesterone 21-hydroxylase, CYP2C [2]
EC 1.14.14.1 Enzyme: progesterone 21-hydroxylase, CYP2B11 [3]
EC 1.14.14.1

References

  1. Ruckpaul, K. and Rein, H., Eds. (1990) Frontiers in Biotransformation, vol. 3: Molecular Mechanisms of Adrenal Steroidogenesis and Aspects of Regulation and Application. Taylor & Francis, London.
  2. Richardson, T.H., Jung, F., Griffin, K.J., Wester, M., Raucy, J.L., Kemper, B., Bornheim, L.M., Hassett, C., Omiecinski, C.J. and Johnson, E.F. (1995) A universal approach to the expression of human and rabbit cytochrome P450s of the 2C subfamily in Escherichia coli. Arch. Biochem. Biophys. 323, 87-96.
  3. Born, S.L., John, G.H., Harlow, G.R. and Halpert, J.R. (1995) Characterization of the progesterone 21-hydroxylase activity of canine cytochrome P450 PBD-2/P450 2B11 through reconstitution, heterologous expression, and site-directed mutagenesis. Drug Metab. Dispos. 23, 702-707.

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