DHSA (original) (raw)
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. A crystal structure of DHSA in complex with M. tuberculosis iron-dependent extradiol dioxygenase has been determined.
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|---|---|
| dbo:abstract | 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. 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. (en) |
| dbo:iupacName | (3aS,4S,7aS)-4-[2-(2,3-Dihydroxy-6-methylphenyl)ethyl]-7a-methylhexahydro-1H-indene-1,5(4H)-dione (en) 3,4-Dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione (en) |
| dbo:thumbnail | wiki-commons:Special:FilePath/DHSA.svg?width=300 |
| dbo:wikiPageID | 24485522 (xsd:integer) |
| dbo:wikiPageLength | 4503 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1043972996 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Catechol dbr:Metabolite dbr:Secosteroid dbr:Cyclic_compound dbr:Enzyme dbr:Comamonas_testosteroni dbr:Tuberculosis dbc:Secosteroids dbr:Redox dbr:Cholesterol dbr:Biphenyl-2,3-diol_1,2-dioxygenase dbr:Metabolism dbr:Catabolism dbr:Hydroxyl dbr:Mycobacterium_tuberculosis dbr:Aromatic_ring dbr:IUPAC_nomenclature dbr:File:DHSA_metabolism.tif |
| dbp:imagefile | DHSA.svg (en) |
| dbp:imagesize | 120 (xsd:integer) |
| dbp:iupacname | 34 (xsd:integer) |
| dbp:pin | -4 (xsd:integer) |
| dbp:verifiedrevid | 443680947 (xsd:integer) |
| dbp:wikiPageUsesTemplate | dbt:Chembox dbt:Chembox_Hazards dbt:Chembox_Identifiers dbt:Chembox_Properties dbt:Clear dbt:Reflist dbt:Chemspidercite dbt:Drugbankcite dbt:Ebicite dbt:Stdinchicite |
| dcterms:subject | dbc:Secosteroids |
| gold:hypernym | dbr:Compound |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q11173 dbo:ChemicalCompound |
| rdfs:comment | 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. A crystal structure of DHSA in complex with M. tuberculosis iron-dependent extradiol dioxygenase has been determined. (en) |
| rdfs:label | DHSA (en) |
| owl:sameAs | freebase:DHSA wikidata:DHSA http://azb.dbpedia.org/resource/دیاچاسای dbpedia-fa:DHSA dbpedia-sh:DHSA dbpedia-sr:DHSA https://global.dbpedia.org/id/4j5j4 |
| prov:wasDerivedFrom | wikipedia-en:DHSA?oldid=1043972996&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/DHSA.svg |
| foaf:isPrimaryTopicOf | wikipedia-en:DHSA |
| is dbo:wikiPageWikiLink of | dbr:Catechol dbr:C19H24O4 dbr:Biphenyl-2,3-diol_1,2-dioxygenase |
| is foaf:primaryTopic of | wikipedia-en:DHSA |
