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phosphatoquinone A
A naphthoquinone that is 1a-methyl-1a,7a-dihydronaphtho[2,3-b]oxirene-2,7-dione substituted at position 7a by a [(2E)-3,7-dimethylocta-2,6-dien-1-yl] group and at positions 3 and 5 by hydroxy groups. It is isolated from the culture broth of Streptomyces sp.TC-0363 and exhibits inhibitory activity against the enzyme protein tyrosine phosphatase.


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03. Biological Effects of Specific Chemicals: biochemical uses [CHEBI:52206] > metabolite [CHEBI:25212] > secondary metabolite [CHEBI:26619] > phosphatoquinone A [CHEBI:66751]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 enzyme inhibitor [CHEBI:23924] (825) 
 protein tyrosine phosphatase inhibitor [CHEBI:35608] (3) 
 phosphatoquinone A [CHEBI:66751] (1)
 metabolite [CHEBI:25212] (2692) 
 secondary metabolite [CHEBI:26619] (2225) 
 phosphatoquinone A [CHEBI:66751] (1)
 antimicrobial agent [CHEBI:33281] (927) 
 antibiotic [CHEBI:22582] (193) 
 phosphatoquinone A [CHEBI:66751] (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) 
 Streptomycetaceae (160) 
 Streptomyces (157)
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) 
 phosphatoquinone A [CHEBI:66751] (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) 
 phosphatoquinone A [CHEBI:66751] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 phosphatoquinone A [CHEBI:66751] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 naphthoquinone [CHEBI:25481] (25) 
 phosphatoquinone A [CHEBI:66751] (1)
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 phosphatoquinone A [CHEBI:66751] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 phosphatoquinone A [CHEBI:66751] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 naphthoquinone [CHEBI:25481] (25) 
 phosphatoquinone A [CHEBI:66751] (1)
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 phosphatoquinone A [CHEBI:66751] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 phosphatoquinone A [CHEBI:66751] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 phosphatoquinone A [CHEBI:66751] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 naphthoquinone [CHEBI:25481] (25) 
 phosphatoquinone A [CHEBI:66751] (1)
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 phosphatoquinone A [CHEBI:66751] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 phosphatoquinone A [CHEBI:66751] (1)
 quinone [CHEBI:36141] (209) 
 naphthoquinone [CHEBI:25481] (25) 
 phosphatoquinone A [CHEBI:66751] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 phosphatoquinone A [CHEBI:66751] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 phosphatoquinone A [CHEBI:66751] (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) 
 naphthoquinone [CHEBI:25481] (25) 
 phosphatoquinone A [CHEBI:66751] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 aromatic compound [CHEBI:33655] (3799) 
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 phosphatoquinone A [CHEBI:66751] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 phosphatoquinone A [CHEBI:66751] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 phosphatoquinone A [CHEBI:66751] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 phosphatoquinone A [CHEBI:66751] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 phosphatoquinone A [CHEBI:66751] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 phosphatoquinone A [CHEBI:66751] (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) 
 naphthoquinone [CHEBI:25481] (25) 
 phosphatoquinone A [CHEBI:66751] (1)
 heteroatomic molecular entity [CHEBI:37577] (13672) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 phenols [CHEBI:33853] (868) 
 phosphatoquinone A [CHEBI:66751] (1)
ChEBI Compound Accession Identifier  [CHEBI:66751]
ChEBI Compound Description  A naphthoquinone that is 1a-methyl-1a,7a-dihydronaphtho[2,3-b]oxirene-2,7-dione substituted at position 7a by a [(2E)-3,7-dimethylocta-2,6-dien-1-yl] group and at positions 3 and 5 by hydroxy groups. It is isolated from the culture broth of Streptomyces sp.TC-0363 and exhibits inhibitory activity against the enzyme protein tyrosine phosphatase.
ChEBI Compound Identification Number  66751
ChEBI InChI Value  InChI=1S/C21H24O5/c1-12(2)6-5-7-13(3)8-9-21-18(24)15-10-14(22)11-16(23)17(15)19(25)20(21,4)26-21/h6,8,10-11,22-23H,5,7,9H2,1-4H3/b13-8+/t20-,21+/m0/s1
ChEBI InChIKey Value  QTORDDSSLVGNHO-BGTMZHHNSA-N
ChEBI Compound Name  phosphatoquinone A
ChEBI SMILES Value  CC(C)=CCC\C(C)=C\C[C@]12O[C@@]1(C)C(=O)c1c(O)cc(O)cc1C2=O
ChEBI Substance ID  160645459
ChEBI URL  ChEBI:66751
ChemSpider ID  8648865
Ontomatica Chemical Accession Key (OnChAKey)  QTORDDSSLVGNHO_BGTMZHHNSA_N_000_000000
PubChem Compound ID  10473454