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{{chembox |
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{{chembox |
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| verifiedrevid = 443557644 |
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| verifiedrevid = 443680947 |
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| ImageFile = DHSA structure.png |
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| ImageFile = DHSA.svg |
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| ImageSize = 120px |
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| ImageSize = 120px |
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| IUPACName = 3,4-Dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione |
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| IUPACName = 3,4-Dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione |
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| SystematicName = (3a''S'',4''S'',7a''S'')-4--7a-methylhexahydro-1''H''-indene-1,5(4''H'')-dione |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo= |
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| CASNo=2168-61-8 |
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| CASNo_Ref = {{Cascite|changed|EPA}} |
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| PubChem=440483 |
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| PubChem=440483 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 15896 |
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| ChEBI = 15896 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB08542 |
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| DrugBank = DB08542 |
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| KEGG = C04793 |
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| SMILES=CC1=C(C(=C(C=C1)O)O)CCC2C3CCC(=O)C3(CCC2=O)C |
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| SMILES=CC1=C(C(=C(C=C1)O)O)CCC2C3CCC(=O)C3(CCC2=O)C |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 389410 |
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| ChemSpiderID = 389410 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI=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 |
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| StdInChI=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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = YUHVBHDSVLKFNI-NJSLBKSFSA-N |
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| StdInChIKey = YUHVBHDSVLKFNI-NJSLBKSFSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>19</sub>H<sub>24</sub>O<sub>4</sub> |
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| Formula=C<sub>19</sub>H<sub>24</sub>O<sub>4</sub> |
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| MolarMass=316.39146 |
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| MolarMass=316.39146 |
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| Appearance= |
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| Appearance= |
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| Density= |
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| Density= |
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| MeltingPt= |
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| BoilingPt= |
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| Solubility= |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| MainHazards= |
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| FlashPt= |
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| FlashPt= |
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| AutoignitionPt = |
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| Autoignition= |
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'''3,4-DHSA''' is an organic compound which is the ] of the ] of ], by the bacteria most commonly responsible for ] ('']'').<ref name="pmid19300498">{{PDB|2ZI8}}; {{cite journal | author = Yam KC, D'Angelo I, Kalscheuer R, Zhu H, Wang JX, Snieckus V, Ly LH, Converse PJ, Jacobs WR, Strynadka N, Eltis LD | title = Studies of a ring-cleaving dioxygenase illuminate the role of cholesterol metabolism in the pathogenesis of Mycobacterium tuberculosis | journal = PLoS Pathog. | volume = 5 | issue = 3 | pages = e1000344 | year = 2009 | month = March | pmid = 19300498 | pmc = 2652662 | doi = 10.1371/journal.ppat.1000344 }}</ref> 3,4-DHSA is an acronym for 3,4-<u>'''d'''</u>i<u>'''h'''</u>ydroxy-9,10-<u>'''s'''</u>eco-<u>'''a'''</u>ndrost-1,3,5(10)-triene-9,17-dione, the ] of this substance. It is classified as a ], since one of the four rings of cholesterol from which it is derived is broken. |
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'''3,4-DHSA''' is an organic compound which is the ] of the ] of ], by the bacteria most commonly responsible for ] ('']'').<ref name="pmid19300498">{{PDB|2ZI8}}; {{cite journal | vauthors = Yam KC, D'Angelo I, Kalscheuer R, Zhu H, Wang JX, Snieckus V, Ly LH, Converse PJ, Jacobs WR, Strynadka N, Eltis LD | title = Studies of a Ring-Cleaving Dioxygenase Illuminate the Role of Cholesterol Metabolism in the Pathogenesis of Mycobacterium tuberculosis | journal = PLOS Pathog. | volume = 5 | issue = 3 | pages = e1000344 |date=March 2009 | pmid = 19300498 | pmc = 2652662 | doi = 10.1371/journal.ppat.1000344 | editor1-last = Ramakrishnan | editor1-first = Lalita | doi-access = free }}</ref> 3,4-DHSA is an acronym for 3,4-<u>'''d'''</u>i<u>'''h'''</u>ydroxy-9,10-<u>'''s'''</u>eco-<u>'''a'''</u>ndrost-1,3,5(10)-triene-9,17-dione, the ] of this substance. It is classified as a ], since one of the four rings of cholesterol from which it is derived is broken. |
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3,4-DHSA is a ]ic intermediate (a compound containing an ] with two adjacent ] groups) produced by ''M. tuberculosis'' during the ] of ].<ref name="pmid19300498"/> 3,4-DHSA is also produced by other bacteria such as '']''.<ref name="pmid15474469">{{cite journal | author = Horinouchi M, Kurita T, Yamamoto T, Hatori E, Hayashi T, Kudo T | title = Steroid degradation gene cluster of Comamonas testosteroni consisting of 18 putative genes from meta-cleavage enzyme gene tesB to regulator gene tesR | journal = Biochem. Biophys. Res. Commun. | volume = 324 | issue = 2 | pages = 597–604 | year = 2004 | month = November | pmid = 15474469 | doi = 10.1016/j.bbrc.2004.09.096 }}</ref><ref name="pmid15555908">{{cite journal | author = Horinouchi M, Hayashi T, Kudo T | title = The genes encoding the hydroxylase of 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione in steroid degradation in Comamonas testosteroni TA441 | journal = J. Steroid Biochem. Mol. Biol. | volume = 92 | issue = 3 | pages = 143–54 | year = 2004 | month = October | pmid = 15555908 | doi = 10.1016/j.jsbmb.2004.09.002 }}</ref> |
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3,4-DHSA is a ]ic intermediate (a compound containing an ] with two adjacent ] groups) produced by ''M. tuberculosis'' during the ] of ].<ref name="pmid19300498"/> 3,4-DHSA is also produced by other bacteria such as '']''.<ref name="pmid15474469">{{cite journal | vauthors = Horinouchi M, Kurita T, Yamamoto T, Hatori E, Hayashi T, Kudo T | title = Steroid degradation gene cluster of Comamonas testosteroni consisting of 18 putative genes from meta-cleavage enzyme gene tesB to regulator gene tesR | journal = Biochem. Biophys. Res. Commun. | volume = 324 | issue = 2 | pages = 597–604 |date=November 2004 | pmid = 15474469 | doi = 10.1016/j.bbrc.2004.09.096 }}</ref><ref name="pmid15555908">{{cite journal | vauthors = Horinouchi M, Hayashi T, Kudo T | title = The genes encoding the hydroxylase of 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione in steroid degradation in Comamonas testosteroni TA441 | journal = J. Steroid Biochem. Mol. Biol. | volume = 92 | issue = 3 | pages = 143–54 |date=October 2004 | pmid = 15555908 | doi = 10.1016/j.jsbmb.2004.09.002 | s2cid = 24549812 }}</ref> |
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A particular type of ] known as ] is responsible for the ] and ] 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.<ref name="pmid19300498"/> |
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A particular type of ] known as ] is responsible for the ] and ] 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.<ref name="pmid19300498"/> |
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A crystal structure of DHSA in complex with ''M. tuberculosis'' iron-dependent extradiol dioxygenase has been determined.<ref name="pmid19300498"/> |
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A crystal structure of DHSA in complex with ''M. tuberculosis'' iron-dependent extradiol dioxygenase has been determined.<ref name="pmid19300498"/> |
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==References== |
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==References== |