dhsa dhsa 3,4-dhsa is an organic compound which is the intermediate product of the metabolism of cholesterol, by the bacteria most commonly responsible for tuberculosis (mycobacterium tuberculosis). 3,4-dhsa is an acronym for 3,4-dihydroxy-9,10-seco-androst-1,3,5(10)-triene-9,17-dione, the official name of this substance. it is classified as a secosteroid, since one of the four rings of cholesterol from which it is derived is broken. dhsa names iupac name 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione systematic iupac name (3as,4s,7as)-4--7a-methylhexahydro-1h-indene-1,5(4h)-dione identifiers 3d model (jsmol) interactive image chebi chebi:15896 y chemspider 389410 y drugbank db08542 y kegg c04793 pubchem cid 440483 inchi inchi=1s/c19h24o4/c1-11-3-7-16(21)18(23)12(11)4-5-13-14-6-8-17(22)19(14,2)10-9-15(13)20/h3,7,13-14,21,23h,4-6,8-10h2,1-2h3/t13-,14-,19-/m0/s1 ykey: yuhvbhdsvlkfni-njslbksfsa-n y smiles cc1=c(c(=c(c=c1)o)o)ccc2c3ccc(=o)c3(ccc2=o)c properties chemical formula c19h24o4 molar mass 316.39146 except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). y verify (what is yn ?) infobox references 3,4-dhsa is a catecholic intermediate (a compound containing an aromatic ring with two adjacent hydroxyl groups) produced by m. tuberculosis during the breakdown of cholesterol. 3,4-dhsa is also produced by other bacteria such as comamonas testosteroni. a particular type of enzyme known as extradiol dioxygenase is responsible for the oxidation and ring opening of 3,4-dhsa to 4,9-dsha (see metabolic scheme below). m. tuberculosis bacteria that are deficient in this enzyme are less lethal than wild-type bacteria. 3,4-dhsa itself appears to be toxic to the bacteria while the breakdown products of 3,4-dhsa can be used as energy source by the bacteria. hence blocking the oxidation of 3,4-dhsa by the extradiol dioxygenase enzyme may be useful in the treatment of tuberculosis. a crystal structure of dhsa in complex with m. tuberculosis iron-dependent extradiol dioxygenase has been determined. synthesis and degradation of 3,4-dhsa.