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CHEBI:66751 - phosphatoquinone A

ChEBI IDCHEBI:66751
ChEBI Namephosphatoquinone A
Stars
DefinitionAn organic heterotricyclic compound resulting from the formal epoxidation of the 2-3 double bond of the 1,4-naphthoquinone moiety of phosphatoquinone B. It is isolated from the culture broth of Streptomyces sp.TC-0363 and exhibits inhibitory activity against the enzyme protein tyrosine phosphatase.
Last Modified7 June 2016
DownloadsMolfile
FormulaC21H24O5
Net Charge0
Average Mass356.418
Monoisotopic Mass356.16237
SMILESCC(C)=CCC/C(C)=C/C[C@]12O[C@@]1(C)C(=O)c1c(O)cc(O)cc1C2=O
InChIInChI=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
InChIKeyQTORDDSSLVGNHO-BGTMZHHNSA-N
Species of MetaboliteComponentSourceComments
Streptomyces sp. (ncbitaxon:1931) - PubMed (10344559) Strain: TA 0363
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor  An EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor which interferes with the activity of the enzyme protein tyrosine phosphatases (PTPs), EC 3.1.3.48, involved in the removal of phosphate groups from phosphorylated tyrosine residues on proteins.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
phosphatoquinone A (CHEBI:66751) has role antimicrobial agent (CHEBI:33281)
phosphatoquinone A (CHEBI:66751) has role EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor (CHEBI:35608)
phosphatoquinone A (CHEBI:66751) has role metabolite (CHEBI:25212)
phosphatoquinone A (CHEBI:66751) is a cyclic ketone (CHEBI:3992)
phosphatoquinone A (CHEBI:66751) is a epoxide (CHEBI:32955)
phosphatoquinone A (CHEBI:66751) is a organic heterotricyclic compound (CHEBI:26979)
phosphatoquinone A (CHEBI:66751) is a phenols (CHEBI:33853)
IUPAC Name 
(1aR,7aS)-7a-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3,5-dihydroxy-1a-methyl-1a,7a-dihydronaphtho[2,3-b]oxirene-2,7-dione
Registry NumbersSources
Reaxys:8168625Reaxys
Citations