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androstenedione degradation

Androstenedione is a key intermediate of microbial steroid metabolism. It is a naturally occurring steroid hormone produced in the gonad or ovary, and an immediate precursor of testosterone in males and estradiol and estrone in females |CITS: [18329874]|. The compound was first isolated in 1931 from a male policeman?s urine and named androsterone (andro = male, ster = sterol, one = ketone) |CITS: [Butenandt34]|. The chemical structure of androsterone was reported soon after |CITS: [Ruzicka34]|. The pathway for the degradation of |FRAME: ANDROST4ENE| was proposed already in 1968 based on analysis of the compounds produced in culture of testosterone-grown |FRAME: TAX-285| |CITS: [Coulter68]|. |FRAME: ANDROST4ENE "Androst-4-en-3,17-dione"| undergoes Δ1-dehydrogenation followed by a 9alpha-hydroxylation to produce |FRAME: CPD-13680|, an unstable compound that rearranges spontaneously to form |FRAME: CPD-13708|, a structure that misses the B ring. The opening of the A ring is achieved by the successive actions of a hydroxylase that hydroxylates the C4 position and a meta-cleavage dioxygenase that opens the ring |CITS: [11739769]|. A hydrolase (|FRAME: G-14727|) then breaks the product into two parts - |FRAME: CPD-13711| (which still contains the intact C and D rings) and |FRAME: CPD-13712| |CITS: [12676694][16151114]|. The latter is believed to be processed by three enzymes, encoded by |FRAME: G-14747|, |FRAME: G-14748| and |FRAME: G-14749|, into |FRAME: PYRUVATE| and |FRAME: PROPIONYL-COA| |CITS: [16151114]|. The degradation of the other product of the hydrolase, |FRAME: CPD-13711|, starts with removal of its side chain in the form of |FRAME: ACETYL-COA| by one beta-oxidation cycle |CITS:[Lee67][Miclo90][Miclo92]| that involves the |FRAME: G-17939| and |FRAME: G-14760| genes |CITS: [21901092][23146019]|. The degradation of the end product of this beta-oxidation cycle, |FRAME: CPD-13759|, has not been characterized yet.

from BIOCYC source record: META_PWY-6944
Type: pathway
Taxonomic scope
conserved biosystem

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