CHEBI:66080 - integrastatin B

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ChEBI Name integrastatin B
ChEBI ID CHEBI:66080
Definition An organic heterotetracyclic compound that is 11,12-dihydro-6H-6,12-epoxydibenzo[b,f]oxocine substituted by hydroxy groups at positions 4, 7 and 8, methoxy groups at positions 3 and 9, methyl groups at positions 6 and 12, an oxo group at position 11 and a formyl group at position 1. It is isolated as a racemate from Ascochyta and exhibits inhibitory activity against HIV-1 integrase.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H18O9
Net Charge 0
Average Mass 402.35150
Monoisotopic Mass 402.09508
InChI InChI=1S/C20H18O9/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/h5-7,22-24H,1-4H3
InChIKey PECRJLBPKXQZDC-UHFFFAOYSA-N
SMILES COc1cc2C(=O)C3(C)OC(C)(Oc4c(O)c(OC)cc(C=O)c34)c2c(O)c1O
Metabolite of Species Details
Ascochyta (NCBI:txid5453) Organism is an endophyte isolated from the leaves of Urtica urens of strain ATCC 74477 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 B (CHEBI:66080) has role HIV-1 integrase inhibitor (CHEBI:67268)
integrastatin B (CHEBI:66080) has role metabolite (CHEBI:25212)
integrastatin B (CHEBI:66080) is a aldehyde (CHEBI:17478)
integrastatin B (CHEBI:66080) is a aromatic ether (CHEBI:35618)
integrastatin B (CHEBI:66080) is a bridged compound (CHEBI:35990)
integrastatin B (CHEBI:66080) is a cyclic ether (CHEBI:37407)
integrastatin B (CHEBI:66080) is a cyclic ketone (CHEBI:3992)
integrastatin B (CHEBI:66080) is a organic heterotetracyclic compound (CHEBI:38163)
integrastatin B (CHEBI:66080) is a polyphenol (CHEBI:26195)
IUPAC Name
4,7,8-trihydroxy-3,9-dimethoxy-6,12-dimethyl-11-oxo-11,12-dihydro-6H-6,12-epoxydibenzo[b,f]oxocine-1-carbaldehyde
Synonym Source
rac-4,7,8-trihydroxy-3,9-dimethoxy-6,12-dimethyl-11-oxo-11,12-dihydro-6H-6,12-epoxydibenzo[b,f]oxocine-1-carbaldehyde ChEBI
Registry Numbers Types Sources
324518-09-4 CAS Registry Number ChemIDplus
9163563 Reaxys Registry Number Reaxys
Last Modified
18 July 2013
General Comment
2013-07-18 Tetrahedron Lett.,43(13), 2351-2354.