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brasiliquinone B
A carbopolycyclic compound that is 3,4-dihydrotetraphene-1,7,12(2H)-trione substituted by hydroxy groups at positions 6 and 8 and an ethyl group at position 3 (the S stereoisomer). It is isolated from the culture broth of Nocardia brasiliensis and exhibits antibacterial activity against Gram-positive bacteria. It is also active against the multiple drug-resistant P388/ADR tumour cells.


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03. Biological Effects of Specific Chemicals: antimicrobial agent [CHEBI:33281]
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05. Industrial Uses: pharmaceutical [CHEBI:52217]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 metabolite [CHEBI:25212] (2692) 
 secondary metabolite [CHEBI:26619] (2225) 
 brasiliquinone B [CHEBI:65517] (1)
 antimicrobial agent [CHEBI:33281] (927) 
 antibiotic [CHEBI:22582] (193) 
 brasiliquinone B [CHEBI:65517] (1)
 antibacterial agent [CHEBI:33282] (317) 
 brasiliquinone B [CHEBI:65517] (1)
05. Industrial Uses 
05. Industrial Uses
 pharmaceutical [CHEBI:52217] (1978) 
 drug [CHEBI:23888] (1930) 
 antineoplastic agent [CHEBI:35610] (760) 
 brasiliquinone B [CHEBI:65517] (1)
06. Name of Biological Source of Chemical 
06. Name of Biological Source of Chemical
 Archaea, Cyanobacteria and Bacteria (302) 
 Eubacteria (239) 
 Firmicutes (214) 
 Actinobacteria (204) 
 Actinobacteridae (204) 
 Actinomycetales (204) 
 Nocardiaceae (9) 
 Nocardia (9) 
 Nocardia brasiliensis (6)
07. Part of Biological Source of Chemical 
07. Part of Biological Source of Chemical
 unspecified structure [PO:0000004] (703)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 s-block molecular entity [CHEBI:33674] (7287) 
 hydrogen molecular entity [CHEBI:33608] (6932) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 polyphenol [CHEBI:26195] (189) 
 brasiliquinone B [CHEBI:65517] (1)
 p-block molecular entity [CHEBI:33675] (25343) 
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 polyphenol [CHEBI:26195] (189) 
 brasiliquinone B [CHEBI:65517] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 brasiliquinone B [CHEBI:65517] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 brasiliquinone B [CHEBI:65517] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 brasiliquinone B [CHEBI:65517] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 polyphenol [CHEBI:26195] (189) 
 brasiliquinone B [CHEBI:65517] (1)
 quinone [CHEBI:36141] (209) 
 brasiliquinone B [CHEBI:65517] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 carbocyclic compound [CHEBI:33598] (1130) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 brasiliquinone B [CHEBI:65517] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 polyphenol [CHEBI:26195] (189) 
 brasiliquinone B [CHEBI:65517] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 brasiliquinone B [CHEBI:65517] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 homocyclic compound [CHEBI:33597] (1134) 
 carbocyclic compound [CHEBI:33598] (1130) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 brasiliquinone B [CHEBI:65517] (1)
 homopolycyclic compound [CHEBI:35295] (493) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 brasiliquinone B [CHEBI:65517] (1)
 polycyclic compound [CHEBI:33635] (4078) 
 homopolycyclic compound [CHEBI:35295] (493) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 brasiliquinone B [CHEBI:65517] (1)
 aromatic compound [CHEBI:33655] (3799) 
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 polyphenol [CHEBI:26195] (189) 
 brasiliquinone B [CHEBI:65517] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 carbocyclic compound [CHEBI:33598] (1130) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 brasiliquinone B [CHEBI:65517] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 polyphenol [CHEBI:26195] (189) 
 brasiliquinone B [CHEBI:65517] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 carbocyclic compound [CHEBI:33598] (1130) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 brasiliquinone B [CHEBI:65517] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 polyphenol [CHEBI:26195] (189) 
 brasiliquinone B [CHEBI:65517] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 brasiliquinone B [CHEBI:65517] (1)
 heteroatomic molecular entity [CHEBI:37577] (13672) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 polyphenol [CHEBI:26195] (189) 
 brasiliquinone B [CHEBI:65517] (1)
ChEBI Compound Accession Identifier  [CHEBI:65517]
ChEBI Compound Description  A carbopolycyclic compound that is 3,4-dihydrotetraphene-1,7,12(2H)-trione substituted by hydroxy groups at positions 6 and 8 and an ethyl group at position 3 (the S stereoisomer). It is isolated from the culture broth of Nocardia brasiliensis and exhibits antibacterial activity against Gram-positive bacteria. It is also active against the multiple drug-resistant P388/ADR tumour cells.
ChEBI Compound Identification Number  65517
ChEBI InChI Value  InChI=1S/C20H16O5/c1-2-9-6-10-8-14(23)17-18(15(10)13(22)7-9)19(24)11-4-3-5-12(21)16(11)20(17)25/h3-5,8-9,21,23H,2,6-7H2,1H3/t9-/m0/s1
ChEBI InChIKey Value  YXEPHAVILJDRHK-VIFPVBQESA-N
ChEBI Compound Name  brasiliquinone B
ChEBI SMILES Value  CC[C@@H]1CC(=O)c2c(C1)cc(O)c1C(=O)c3c(O)cccc3C(=O)c21
ChEBI Substance ID  160644956
ChEBI URL  ChEBI:65517
ChemSpider ID  8059861
Ontomatica Chemical Accession Key (OnChAKey)  YXEPHAVILJDRHK_VIFPVBQESA_N_000_000000
PubChem Compound ID  9884187