CHEBI:66006 - harziphilone

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ChEBI Name harziphilone
ChEBI ID CHEBI:66006
Definition A member of the class of isochromanes that is 1,5,6,7-tetrahydro-8H-isochromen-8-one substituted by hydroxy groups at positions 6 and 7, a methyl group at position 7 and a penta-1,3-dien-1-yl moiety at position 3. Isolated from the fermentation broth of Trichoderma harzianum, it exhibits anti-HIV activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C15H18O4
Net Charge 0
Average Mass 262.30100
Monoisotopic Mass 262.12051
InChI InChI=1S/C15H18O4/c1-3-4-5-6-11-7-10-8-13(16)15(2,18)14(17)12(10)9-19-11/h3-7,13,16,18H,8-9H2,1-2H3/b4-3+,6-5+/t13-,15-/m1/s1
InChIKey GFTDIFRKHSPLIX-VNLWOOSYSA-N
SMILES C\C=C\C=C\C1=CC2=C(CO1)C(=O)[C@](C)(O)[C@H](O)C2
Metabolite of Species Details
Trichoderma harzianum (NCBI:txid5544) See: PubMed
Roles Classification
Biological Role(s): anti-HIV agent
An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
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 harziphilone (CHEBI:66006) has role anti-HIV agent (CHEBI:64946)
harziphilone (CHEBI:66006) has role metabolite (CHEBI:25212)
harziphilone (CHEBI:66006) is a aromatic ketone (CHEBI:76224)
harziphilone (CHEBI:66006) is a diol (CHEBI:23824)
harziphilone (CHEBI:66006) is a enone (CHEBI:51689)
harziphilone (CHEBI:66006) is a isochromanes (CHEBI:38762)
harziphilone (CHEBI:66006) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name
rel-(6R,7R)-6,7-dihydroxy-7-methyl-3-[(1E,3E)-penta-1,3-dien-1-yl]-1,5,6,7-tetrahydro-8H-isochromen-8-one
Registry Numbers Types Sources
183239-75-0 CAS Registry Number ChemIDplus
7590687 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15232001 PubMed citation Europe PMC
8968392 PubMed citation Europe PMC
Last Modified
07 February 2018
General Comment
2013-02-19 The hydroxy group at C-3 is trans to the methyl group at position C-2. The absolute stereochemistry, however, has not been determined.