CHEBI:66079 - integrastatin A

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ChEBI Name integrastatin A
ChEBI ID CHEBI:66079
Definition An organic heterotetracyclic compound that is 6H-6,12-epoxydibenzo[b,f]oxocin-11(12H)-one substituted by hydroxy groups at positions 4, 7 and 8, a hydroxymethyl group position 1, methyl groups at positions 6 and 12 and methoxy groups at positions 3 and 9. It is isolated as a racemate from Unidentified fungi (New mexico) and has been shown to exhibit inhibitory activity against HIV-1 integrase.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H20O9
Net Charge 0
Average Mass 404.36740
Monoisotopic Mass 404.11073
InChI InChI=1S/C20H20O9/c1-19-12-8(7-21)5-10(26-3)15(23)17(12)28-20(2,29-19)13-9(18(19)25)6-11(27-4)14(22)16(13)24/h5-6,21-24H,7H2,1-4H3
InChIKey LNYIJBSSELCSKA-UHFFFAOYSA-N
SMILES COc1cc2C(=O)C3(C)OC(C)(Oc4c(O)c(OC)cc(CO)c34)c2c(O)c1O
Metabolite of Species Details
Unidentified fungi (New mexico) of strain ATCC 74478 See: DOI
Roles Classification
Biological Role(s): HIV-1 integrase inhibitor
An inhibitor of HIV-1 integrase, an enzyme required for the integration of the genetic material of the retrovirus into the DNA of the infected cells.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing integrastatin A (CHEBI:66079) has role HIV-1 integrase inhibitor (CHEBI:67268)
integrastatin A (CHEBI:66079) has role metabolite (CHEBI:25212)
integrastatin A (CHEBI:66079) is a aromatic ether (CHEBI:35618)
integrastatin A (CHEBI:66079) is a bridged compound (CHEBI:35990)
integrastatin A (CHEBI:66079) is a cyclic ether (CHEBI:37407)
integrastatin A (CHEBI:66079) is a cyclic ketone (CHEBI:3992)
integrastatin A (CHEBI:66079) is a organic heterotetracyclic compound (CHEBI:38163)
integrastatin A (CHEBI:66079) is a polyphenol (CHEBI:26195)
integrastatin A (CHEBI:66079) is a primary alcohol (CHEBI:15734)
IUPAC Name
4,7,8-trihydroxy-1-(hydroxymethyl)-3,9-dimethoxy-6,12-dimethyl-6H-6,12-epoxydibenzo[b,f]oxocin-11(12H)-one
Synonym Source
rac-4,7,8-trihydroxy-1-(hydroxymethyl)-3,9-dimethoxy-6,12-dimethyl-6H-6,12-epoxydibenzo[b,f]oxocin-11(12H)-one ChEBI
Registry Number Type Source
9166117 Reaxys Registry Number Reaxys
Last Modified
18 July 2013
General Comment
2013-07-18 Tetrahedron Lett.,43(13), 2351-2354.