CHEBI:66751 - phosphatoquinone A

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ChEBI Name phosphatoquinone A
ChEBI ID CHEBI:66751
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5855401, ZINC000005854633
Download Molfile XML SDF
Formula C21H24O5
Net Charge 0
Average Mass 356.41230
Monoisotopic Mass 356.16237
InChI 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
InChIKey QTORDDSSLVGNHO-BGTMZHHNSA-N
SMILES CC(C)=CCC\C(C)=C\C[C@]12O[C@@]1(C)C(=O)c1c(O)cc(O)cc1C2=O
Metabolite of Species Details
Streptomyces sp. (NCBI:txid1931) of strain TA 0363 See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
8168625 Reaxys Registry Number Reaxys
Citation Type Source
10344559 PubMed citation Europe PMC
Last Modified
07 June 2016