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CHEBI:66079 - integrastatin A

ChEBI IDCHEBI:66079
ChEBI Nameintegrastatin A
Stars
DefinitionAn 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.
Last Modified8 November 2024
DownloadsMolfile
FormulaC20H20O9
Net Charge0
Average Mass404.371
Monoisotopic Mass404.11073
SMILESCOc1cc2c(c(O)c1O)C1(C)Oc3c(O)c(OC)cc(CO)c3C(C)(O1)C2=O
InChIInChI=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
InChIKeyLNYIJBSSELCSKA-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
unclassified Fungi (ncbitaxon:89443) - DOI (10.1016/S0040-4039(02)00265-4) Strain: ATCC74478
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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)-oneChEBI
Registry NumbersSources
Reaxys:9166117Reaxys